The Ultimate Midwest Road Trip Itinerary From Chicago (Updated 2024)

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My ultimate Midwest road trip itinerary from Chicago is your ticket to exploring the heartland of America! Starting in the bustling city of Chicago, this journey will take you through charming towns, vibrant cities, and scenic landscapes that showcase the true spirit of the Midwest.

With my guide, you’ll have a blast exploring at a relaxed pace, hitting all the must-see spots without spending too much time behind the wheel. From iconic landmarks to mouth-watering food spots and stunning natural wonders, this road trip has it all. Now, pack your bags and let’s dive into the ultimate Midwest adventure!

Planning the Most Incredible Midwest Road Trip

Road Trip Itinerary Map for the Pacific Northwest

Days 1-2: Chicago, Illinois

Welcome to the start of your epic Midwest road trip! We’re kicking things off in the Windy City, Chicago. Get ready to dive into a city bursting with culture, history, and some seriously good eats.

From iconic skyscrapers and world-class museums to deep-dish pizza and scenic riverwalks, Chicago has it all, making it one of the top places to live and visit in the Midwest. Buckle up and let’s explore everything this incredible city has to offer before we hit the road on our Midwest adventure!

Here are my favorite spots:

• Millennium Park: Start your Chicago adventure at Millennium Park. Snap a selfie with the famous “Bean” sculpture (Cloud Gate) and take a stroll through the beautiful Lurie Garden. If you’re visiting in the summer, catch a free concert at the Jay Pritzker Pavilion. In the winter, ice skating at the McCormick Tribune Plaza is a must!
• Navy Pier: Head to Navy Pier for a mix of entertainment, dining, and stunning lake views. Ride the Centennial Wheel for panoramic views of the city and Lake Michigan. Check out the Chicago Shakespeare Theater for a play or enjoy some delicious Chicago-style popcorn from Garrett Popcorn Shops.
• Art Institute of Chicago: Art lovers, this one’s for you! The Art Institute is home to an impressive collection of artworks, including Grant Wood’s “American Gothic” and Georges Seurat’s “A Sunday on La Grande Jatte.” Don’t miss the Thorne Miniature Rooms – they’re fascinating!
• The Magnificent Mile: Shop till you drop along Michigan Avenue, also known as The Magnificent Mile. From high-end boutiques to popular chain stores, there’s something for every shopper. During the holiday season, the lights and decorations are simply magical.
• Chicago Riverwalk: Take a leisurely walk along the Chicago Riverwalk. It’s a great place to relax, grab a bite to eat, and watch the boats go by.

More Things to Do in Chicago

• Willis Tower Skydeck: Brave the Skydeck at Willis Tower (formerly Sears Tower) for breathtaking views from 1,353 feet above the ground. Step out onto The Ledge, a glass balcony extending four feet outside the building – not for the faint of heart!
• Wrigley Field: If you’re a sports fan, catch a Cubs game at the historic Wrigley Field. Even if it’s not baseball season, you can take a tour of the stadium and learn about its storied past.
• Deep-Dish Pizza: You can’t leave Chicago without trying its iconic deep-dish pizza. Head to Lou Malnati’s, Giordano’s, or Gino’s East for a slice of cheesy, saucy heaven. Pro tip: It takes a while to bake, so order an appetizer or two while you wait.
• Museum of Science and Industry: This massive museum is perfect for families and curious minds of all ages. Explore interactive exhibits like the U-505 submarine, a working coal mine, and a fantastic mirror maze.
• Lincoln Park Zoo: One of the oldest zoos in the country, Lincoln Park Zoo offers free admission and a variety of animals to see. It’s a great spot for a relaxing afternoon, and during the winter, the zoo’s holiday lights display is a real treat.

For a scenic and active way to explore, rent bikes and ride along the Lakefront Trail. It stretches for 18 miles and offers stunning views of Lake Michigan and the skyline. If you plan on hitting multiple attractions, consider getting a CityPass. It gives you discounted entry to top spots like the Art Institute, Shedd Aquarium, and Skydeck.

Day 3: Milwaukee, Wisconsin

Next, drive about an hour and a half north to Milwaukee, Wisconsin. This city is not just about beer and brats (though they are fantastic here). Milwaukee is bursting with unique attractions, from its fascinating brewing heritage to its stunning lakefront.

Known as the “City of Festivals,” Milwaukee hosts a variety of cultural and music festivals year-round. Plus, it’s home to the world-famous Harley-Davidson motorcycles.

I recommend spending at least a day here, as it’s a popular day trip from Chicago. However, 2-3 days is even better if your schedule allows it!

Let’s explore the top spots you shouldn’t miss:

• Milwaukee Art Museum: Home to an impressive collection of over 25,000 works of art, this museum is a must-visit. Don’t miss the stunning Quadracci Pavilion, designed by Santiago Calatrava, with its “wings” that open and close.
• Harley-Davidson Museum: Celebrate Milwaukee’s iconic motorcycle brand. The museum showcases over 450 motorcycles and artifacts. Even if you’re not a motorcycle enthusiast, the history and design elements are fascinating.
• Historic Third Ward: This trendy district is packed with boutique shops, art galleries, and some of the city’s best restaurants. It’s a great place to wander, shop, and dine. Check out the Milwaukee Public Market for a taste of local flavors.
• Lakefront Brewery: Milwaukee is famous for its beer, and Lakefront Brewery offers one of the best tours in the city. It’s fun, informative, and ends with a tasting. Plus, the riverfront beer garden is a perfect spot to relax.
• Milwaukee Riverwalk: Stroll along the scenic Riverwalk, which stretches for nearly three miles through the heart of downtown. Along the way, you’ll find public art installations, charming cafes, lively bars, and unique restaurants.

More Sights to See

• Mitchell Park Horticultural Conservatory (The Domes): Explore these three unique domes, each showcasing a different environment: tropical, desert, and floral show. It’s a lovely spot for plant lovers and families.
• Bradford Beach: On a sunny day, head to Bradford Beach. It’s a great spot for sunbathing, volleyball, and people-watching. There are also some cool beach bars where you can grab a drink.
• Pabst Mansion: Step back in time with a visit to the Pabst Mansion, the former home of Captain Frederick Pabst, founder of Pabst Brewing Company. The mansion is beautifully preserved and offers a glimpse into Milwaukee’s brewing history.
• Summerfest Grounds: If you’re visiting in late June or early July, don’t miss Summerfest, the world’s largest music festival. Even outside of festival season, the grounds are worth a visit for various events and concerts.

The city is walkable, but if you need to get around, the Milwaukee County Transit System (buses) is a reliable option. Bublr Bikes, a bike-sharing program, is also a fun way to explore.

Tip: Milwaukee is known as Brew City for a reason. Book a few brewery tours in advance to avoid missing out, especially during peak tourist season.

Day 4: Madison, Wisconsin

Nestled between two picturesque lakes, Madison is home to the University of Wisconsin-Madison, adding a youthful energy and tons of cultural events to the mix. Known for its bike-friendly streets, farmers’ markets, and an awesome food scene, Madison is a gem you don’t want to miss on your road trip.

Don’t miss these top attractions:

• Wisconsin State Capitol: Kick off your visit with a tour of the stunning Wisconsin State Capitol. This architectural beauty has a dome that offers 360-degree views of the city. And the best part? Free tours are available daily.
• State Street: This lively pedestrian street connects the Capitol to the university campus. It’s lined with quirky shops, delicious eateries, and cool cafes. Perfect for a leisurely stroll and some people-watching.
• University of Wisconsin-Madison Campus: Wander through the picturesque campus. Don’t miss the Memorial Union Terrace, where you can relax by the lake with a scoop of Babcock ice cream, a campus favorite.
• Olbrich Botanical Gardens: These beautiful gardens are a treat year-round. Explore the indoor Bolz Conservatory and stroll through the outdoor gardens. In the summer, the Thai Pavilion is especially stunning.
• Henry Vilas Zoo: This free zoo is a hit with families. From exotic animals to a fun playground, it’s a great spot to spend a few hours.

More Attractions in Madison

• Lake Mendota and Lake Monona: Madison is sandwiched between two beautiful lakes. Rent a kayak or paddleboard, or simply enjoy a lakeside picnic.
• Chazen Museum of Art: Located on the university campus, this museum has an impressive collection of works ranging from ancient to contemporary. Best of all, admission is free.
• Dane County Farmers’ Market: If you’re here on a Saturday, don’t miss the Dane County Farmers’ Market around the Capitol Square. It’s the largest producer-only farmers’ market in the U.S. and a great place to sample local produce and goodies.

If you’re visiting in the warmer months, take advantage of the lakes. Rent a kayak or paddleboard from Brittingham Boats or Wingra Boats. If you prefer to stay on land, there are beautiful walking and biking trails around the lakes.

Days 5-6: Door County, Wisconsin

After soaking in the college-town vibes of Madison, it’s time to head northeast for about three hours to the stunning Door County, Wisconsin. Often referred to as the “Cape Cod of the Midwest,” Door County is a gem in Wisconsin known for its charming small towns, beautiful shoreline, and endless outdoor activities.

With 300 miles of scenic shoreline along Lake Michigan, it’s the perfect spot to unwind and enjoy some of Wisconsin’s landscapes.

Here’s what to do in Door County:

• Peninsula State Park: Start your Door County adventure with a visit to Peninsula State Park. This massive park offers everything from hiking and biking trails to scenic overlooks and a historic lighthouse. The Eagle Trail is a favorite for its stunning views of the bluffs and shoreline.
• Fish Creek: This charming town is a great base for exploring the county. Stroll through Fish Creek’s quaint downtown area, filled with boutiques, art galleries, and cozy cafes. Don’t miss a meal at Wild Tomato for some of the best wood-fired pizza around.
• Scenic Boat Tour: Get out on the water with a scenic boat tour of the Door County coastline. You’ll have a chance to see the iconic bluffs, lighthouses, and maybe even some shipwrecks beneath the clear waters.
• Cave Point County Park: Known for its dramatic limestone cliffs and underwater caves, Cave Point County Park is a must-see. The hiking trails offer stunning views, and if you’re feeling adventurous, consider renting a kayak to explore the caves up close.
• Fish Boil Dinner: Experience a traditional Door County fish boil, a unique local dining tradition. The White Gull Inn in Fish Creek and the Old Post Office in Ephraim are two of the best spots to enjoy this entertaining and delicious meal.

Day Trip Idea from Door County

Day 7: Wisconsin Dells, Wisconsin

• Noah’s Ark Waterpark: As the largest waterpark in the United States, Noah’s Ark boasts over 50 rides and attractions. From the adrenaline-pumping Black Anaconda water coaster to the relaxing lazy river, there’s something for everyone. Pro tip: Arrive early to snag a good spot and avoid the longest lines.
• Wisconsin Deer Park: This unique petting zoo lets you walk among and feed friendly deer. It’s a hit with kids and a great place for some up-close animal encounters. Bring some quarters for the deer feed machines!
• Upper Dells Boat Tour: Explore the stunning rock formations and cliffs along the Wisconsin River on a scenic boat tour. Highlights include the narrow Witches Gulch and the iconic Stand Rock, where you can see the famous dog leap.
• Mt. Olympus Water & Theme Park: A combo of water slides, roller coasters, and go-karts. Don’t miss Hades 360, a wooden coaster with a 360-degree loop! There’s also a cool indoor theme park if the weather isn’t great.
• Tommy Bartlett Exploratory: This hands-on science center is packed with over 175 interactive exhibits, including a Russian space station MIR core module. It’s perfect for curious minds and a great rainy-day activity.

Other Top Spots

Consider staying at a resort with its own waterpark, like the Wilderness Resort or Kalahari Resorts. This can save you time and money, as park admission is often included. Don’t forget to look for combo tickets or passes that offer discounts to multiple attractions. Many hotels also offer packages that include tickets to nearby waterparks and attractions.

Days 8-9: Minneapolis, Minnesota

Minneapolis is home to the famous Mall of America, a thriving arts community, and an extensive network of bike trails. Nestled along the Mississippi River, it’s a perfect blend of urban sophistication and natural beauty.

Here are my favorite spots to visit:

• Minneapolis Institute of Art: This world-class museum houses over 90,000 works of art, ranging from ancient artifacts to contemporary masterpieces. Admission is free, and the collection is diverse and fascinating. Pro tip: Don’t miss the Asian art section; it’s one of the best in the country.
• Mall of America: More than just a shopping center, the Mall of America features an indoor amusement park, an aquarium, and countless dining options. Plan to spend a good part of your day here. If you’re traveling with kids, Nickelodeon Universe is a must-visit.
• Minnehaha Park: One of Minneapolis’s most beautiful parks, featuring the stunning Minnehaha Falls. There are lovely walking trails, picnic spots, and even a historic train depot. In the winter, the frozen falls are a spectacular sight.
• Walker Art Center and Minneapolis Sculpture Garden: Explore contemporary art at the Walker Art Center and then head outside to the Sculpture Garden. The iconic Spoonbridge and Cherry sculpture is a must-see and makes for a great photo op.
• Mississippi Riverfront: Take a stroll along the riverfront and enjoy the scenic views. Stone Arch Bridge offers fantastic views of the city skyline and St. Anthony Falls. It’s a perfect spot for a walk or bike ride.

Other Sights to See

• Uptown Minneapolis: This trendy neighborhood is known for its eclectic mix of shops, restaurants, and nightlife. Check out Calhoun Square and take a walk around Lake Bde Maka Ska (formerly Lake Calhoun).
• Guthrie Theater: Catch a play at this renowned theater, known for its stunning architecture and excellent productions. Even if you’re not seeing a show, the Endless Bridge offers amazing views of the Mississippi River.
• Mill City Museum: Located in the ruins of an old flour mill, this museum offers a fascinating look at Minneapolis’s industrial history. The interactive exhibits are great for all ages.
• Como Park Zoo and Conservatory: Just a short drive away in nearby St. Paul, this zoo and conservatory are free (donations encouraged) and offer a great mix of animals, plants, and beautiful gardens.

Minneapolis boasts a fantastic food scene. Try the Juicy Lucy (a cheese-stuffed burger) at local favorites like Matt’s Bar or the 5-8 Club. For a fine dining experience, visit Spoon and Stable or The Bachelor Farmer.

Weekend Getaway Idea: Duluth and North Shore, Minnesota

If you have a couple of extra days, consider a weekend getaway to Duluth and the North Shore. Just a 2.5-hour drive from Minneapolis, this area is a nature lover’s paradise. Highlights include the breathtaking views of Lake Superior, the historic Split Rock Lighthouse, and the cascading waterfalls at Gooseberry Falls State Park.

The scenic drive along Highway 61 is one of the most beautiful in the Midwest, offering stunning vistas of rugged cliffs, dense forests, and the endless expanse of the lake!

Alternative Idea: Apostle Islands, Wisconsin

Less than a two-hour drive from Duluth, you’ll find the stunning Apostle Islands National Lakeshore. Head to the charming town of Bayfield, where you can hop on a cruise to explore the 21 islands that make up the Apostle Islands. Known for their sea caves, historic lighthouses, and pristine beaches, these islands are a hidden gem in the Midwest.

Days 10-11: Des Moines, Iowa

This vibrant city about three and a half hours south of Minneapolis is bursting with artsy vibes, lush parks, and a growing foodie scene. Known for its friendly locals and a mix of urban and natural attractions, Des Moines offers Midwest charm and modern amenities. Whether you’re exploring the historic downtown or enjoying outdoor activities, there’s something for everyone.

Here are my recommendations:

• Pappajohn Sculpture Park: Located in the heart of downtown, this 4.4-acre park features over 30 sculptures from renowned artists. It’s a perfect spot for a leisurely stroll and some Instagram-worthy photos.
• Iowa State Capitol: This stunning building with its gold dome is a must-visit in Iowa. Take a guided tour to learn about Iowa’s history and government. The view from the top of the dome is breathtaking!
• Des Moines Art Center: Housing an impressive collection of modern and contemporary art, the Des Moines Art Center is a cultural gem. Admission is free, and the architecture of the building itself is worth the visit.
• Downtown Farmers’ Market: If you’re visiting on a Saturday (May to October), don’t miss the Downtown Farmers’ Market. It’s one of the best in the country, offering fresh produce, local crafts, and delicious food.
• Gray’s Lake Park: A beautiful urban oasis, Gray’s Lake Park is perfect for outdoor activities. Rent a paddleboat, kayak, or simply enjoy a walk around the 2-mile trail. The views of the city skyline are fantastic.

More Top Attractions

• Science Center of Iowa: A hit with families, this interactive museum features hands-on exhibits, an IMAX theater, and planetarium shows. It’s a fun and educational experience for all ages.
• East Village: This historic district is packed with unique shops, trendy restaurants, and vibrant nightlife. It’s a great place to explore on foot and find some hidden gems.
• Principal Park: Catch a minor league baseball game at Principal Park, home of the Iowa Cubs. The stadium offers great views of the downtown skyline and the Des Moines River.
• Des Moines Botanical Garden: Explore the lush indoor conservatory and beautiful outdoor gardens. It’s a peaceful retreat with a variety of plant collections.

In the fall, take a scenic drive or bike ride along the High Trestle Trail to see the fall foliage. The trail’s iconic bridge is beautifully lit up at night. Des Moines has a great network of bike trails. Rent a bike and explore the city on two wheels. The Meredith Trail connects many of the city’s top attractions.

Days 12-13: Kansas City, Missouri

It’s time to head south for about three hours to Kansas City, Missouri. Known for its jazz heritage, mouth-watering BBQ, and fountains that rival Rome, Kansas City is a vibrant and welcoming city with plenty to explore. The drive down I-35 is straightforward, and once you arrive, you’ll find a city that effortlessly blends Midwestern charm with a dynamic cultural scene.

Check out my favorite attractions:

• National WWI Museum and Memorial: Start your visit with a dose of history at the National WWI Museum and Memorial. It’s the only museum in the U.S. dedicated to World War I and offers powerful exhibits and stunning views of the city from the Liberty Memorial tower.
• Country Club Plaza: This historic shopping district is the perfect place to stroll, shop, and dine. With its Spanish-inspired architecture and beautiful fountains, the Plaza is a Kansas City icon. Enjoy a meal at one of the many restaurants, or just wander through the boutique shops.
• Nelson-Atkins Museum of Art: Home to a world-class art collection, the Nelson-Atkins Museum of Art is famous for its giant shuttlecock sculptures on the front lawn. Inside, you’ll find everything from ancient artifacts to modern masterpieces. Best of all, admission is free.
• Arthur Bryant’s Barbeque: Kansas City is famous for its BBQ, and Arthur Bryant’s is one of the best restaurants in the city. Dig into some ribs, brisket, or pulled pork, all slathered in the legendary sauce. It’s a must-visit for any BBQ lover.

More Epic Experiences in Kansas

• Jazz District at 18th & Vine: Kansas City is the birthplace of jazz, and the 18th & Vine District is where it all began. Visit the American Jazz Museum to learn about the history of this genre, then catch some live music at one of the nearby clubs.
• Boulevard Brewing Company: Take a tour of Kansas City’s beloved Boulevard Brewing Company. Learn about the brewing process, sample some beers, and enjoy the laid-back atmosphere. The brewery also has a great beer garden for those sunny afternoons.
• Kauffman Center for the Performing Arts: If you’re into the arts, check out what’s playing at the Kauffman Center. The building itself is an architectural marvel, and it hosts everything from opera and ballet to Broadway shows.
• Westport: One of Kansas City’s oldest neighborhoods, Westport is known for its lively nightlife, eclectic shops, and historic charm. It’s a great place to spend an evening, whether you’re grabbing dinner, listening to live music, or just people-watching.

Kansas City is pretty spread out, so having a car is handy. However, the KC Streetcar is free and runs through the downtown area, making it easy to explore the city center without worrying about parking.

Day 14: Springfield, Illinois

From St. Louis, it’s about a 1.5-hour drive north to Springfield, Illinois. This city in Illinois is steeped in history and best known as the hometown of Abraham Lincoln. Walking through Springfield is like stepping back in time, with plenty of historical sites and charming old neighborhoods. Beyond the Lincoln legacy, Springfield offers unique attractions and a friendly, small-town vibe.

Add these spots to your Midwest itinerary:

• Abraham Lincoln Presidential Library and Museum: Dive into Lincoln’s life and legacy at this impressive museum. The exhibits are interactive and engaging, making it a great stop for history buffs and families alike.
• Lincoln Home National Historic Site: Visit the only home Abraham Lincoln ever owned. The house is preserved as it was in Lincoln’s time, and the guided tours are fantastic for getting a real sense of his life before the presidency.
• Old State Capitol: This historic building is where Lincoln delivered his famous “House Divided” speech. Take a guided tour to learn about its role in Illinois’ history and see where Lincoln worked as a lawyer.
• Lincoln Tomb: Located in Oak Ridge Cemetery, the Lincoln Tomb is a somber and beautiful memorial. Don’t forget to rub the nose of Lincoln’s bronze bust at the entrance for good luck!
• Illinois State Museum: Explore Illinois’ natural history, art, and cultural heritage. The museum is family-friendly and offers a mix of permanent and rotating exhibits.

More Sights to Explore

• Dana-Thomas House: Designed by Frank Lloyd Wright, this house is a masterpiece of Prairie School architecture. The guided tours provide fascinating insights into Wright’s design philosophy and the house’s unique features.
• Route 66 Drive-In: Catch a movie at this retro drive-in theater, a nod to the historic Route 66 that runs through Springfield. It’s a fun way to unwind in the evening.
• Downtown Springfield: Wander through the charming downtown area, filled with boutique shops, cafes, and historical landmarks. The Old Capitol Farmers Market is a great spot to pick up local produce and crafts if you’re visiting on a Saturday.

Summer is festival season in Springfield. The Illinois State Fair in August is a must-visit for fun rides, live music, and delicious fair food!

Day Trip or Weekend Getaway from Springfield: The Ozarks

Just a short 1.5 to 2-hour drive from Springfield, Missouri, lies the beautiful and expansive Ozarks region. The Ozarks, known for their rolling hills, deep forests, and pristine rivers, offer a serene escape from city life with endless opportunities for outdoor adventures.

One of the highlights of the Ozarks is the Ozark National Scenic Riverways, America’s first national park dedicated to protecting a river system. This area is famous for its clear, spring-fed rivers—the Current River and the Jacks Fork River—which are ideal for canoeing, kayaking, and fishing. The rivers wind through scenic landscapes, dotted with towering bluffs, caves, and abundant wildlife, making it a paradise for nature lovers.

If you’re into hiking, the Ozarks offer numerous trails, from easy walks to more challenging treks, with many leading to beautiful overlooks and waterfalls. Alley Spring and Mill, a historic site within the riverways, is a must-visit, offering picturesque views and a glimpse into the region’s past.

For a weekend stay, consider camping by the river or staying in one of the cozy cabins or lodges scattered throughout the area. The Ozarks are also home to several quaint towns where you can enjoy local cuisine, browse antique shops, and experience the warm hospitality of the region.

Days 15-16: St. Louis, Missouri

This city is packed with history, incredible food, and tons of cool attractions. Known as the Gateway to the West, St. Louis has a bit of everything – from its iconic arch to vibrant neighborhoods and a rich music scene. Whether you’re a sports fan, foodie, or history buff, you’re going to love it here.

These are the must-see spots:

• Gateway Arch: The Gateway Arch is the tallest monument in the U.S., standing at 630 feet. Take the tram ride to the top for killer views of the city and the Mississippi River. Don’t forget to check out the museum at the base – it’s packed with cool exhibits about America’s westward expansion.
• Forest Park: This place is huge – it’s even bigger than Central Park! You’ve got the St. Louis Zoo (and it’s free), the St. Louis Art Museum, and paddleboats you can rent on the waterways. It’s the perfect spot to spend a whole day exploring.
• City Museum: City Museum is like a giant playground for all ages, with slides, tunnels, and some of the craziest art installations you’ve ever seen.
• Busch Stadium: If you’re into baseball, catching a Cardinals game at Busch Stadium is a must. Even if it’s the offseason, take a tour of the stadium. The view of the city skyline from inside is pretty epic.

More Attractions in St. Louis

• The Hill: This historic Italian neighborhood is foodie heaven. Grab some toasted ravioli at Charlie Gitto’s or Mama’s on The Hill. It’s a local specialty and ridiculously delicious.
• Anheuser-Busch Brewery: Take a tour of this iconic brewery – it’s a St. Louis staple. You’ll learn about the beer-making process, get some free samples, and maybe even see the famous Budweiser Clydesdales.
• Missouri Botanical Garden: One of the oldest botanical gardens in the U.S., this place is stunning. Wander through the Climatron, a huge geodesic dome filled with tropical plants, or just enjoy the beautiful seasonal displays.
• Soulard: Known for its live music and the historic Soulard Farmers Market, which is one of the oldest in the country. It’s a great spot to grab some fresh produce, local goods, and enjoy some tunes.

St. Louis has a great food scene. Don’t leave without trying St. Louis-style BBQ – Pappy’s Smokehouse is a local favorite and one of the unique restaurants in St. Louis. For dessert, grab a slice of gooey butter cake at Park Avenue Coffee. The MetroLink light rail system is a convenient way to get around downtown and to the airport. Day passes are affordable and save you the hassle of parking.

Days 17-18: Shawnee National Forest, Illinois

After exploring St. Louis, it’s time to switch gears and immerse yourself in the natural beauty of Shawnee National Forest in southern Illinois.

Just a two-hour drive east along I-64 and then south on IL-127 will bring you to this stunning area, known for its unique rock formations, lush forests, and scenic trails. If you’re looking to reconnect with nature, this is the perfect spot.

Top Attractions in Shawnee National Forest

• Garden of the Gods: Start your visit at the Garden of the Gods, one of the most iconic spots in Shawnee. The Observation Trail is a short, easy hike that offers breathtaking views of dramatic rock formations and the surrounding forest. Sunrise and sunset here are particularly magical.
• Ferne Clyffe State Park: A bit off the beaten path, Ferne Clyffe offers beautiful hiking trails, waterfalls, and picturesque picnic spots. The Hawk’s Cave Trail is a favorite, leading you through a lush forest to a massive rock shelter.
• Rim Rock Recreational Trail: This moderate trail takes you through a variety of landscapes, from towering rock bluffs to dense woodlands. The trail is well-marked and offers several scenic overlooks. It’s especially beautiful in the fall when the leaves change color.
• Pomona Natural Bridge: A short hike leads you to this impressive natural bridge, formed over thousands of years by erosion. It’s a hidden gem that’s well worth the visit.
• Bell Smith Springs: If you’re up for some more adventure, head to Bell Smith Springs. The area offers multiple hiking trails, natural rock formations, and clear, spring-fed pools. The Devil’s Backbone is a highlight, with a narrow ridge offering incredible views.
• Shawnee Hills Wine Trail: If you’re in the mood for something a little different, take a break from hiking and explore the Shawnee Hills Wine Trail. The area is home to several wineries where you can relax and enjoy local wines in a beautiful setting.

If you’re up for camping, Shawnee has several great spots. Garden of the Gods has a campground with basic facilities, or you can opt for more secluded backcountry camping.

Day 19: Mammoth Cave National Park, Kentucky

Your next destination takes you to one of the most impressive underground wonders in the world: Mammoth Cave National Park in Kentucky. This drive will take you around four hours southeast. Once you reach Cave City, you’re just a short drive away from the park’s entrance.

Mammoth Cave is the longest cave system in the world, with more than 400 miles of explored passageways. Whether you’re a seasoned caver or just curious about what lies beneath, this park offers an unforgettable experience.

Things to Do in Mammoth Cave

• Cave Tours: The highlight of any visit is exploring the cave itself. There are several guided tours available, ranging from easy walks to more strenuous adventures. The Historic Tour is a great starting point, taking you through some of the most famous parts of the cave, including Mammoth Dome and Fat Man’s Misery.
• Frozen Niagara Tour: If you’re short on time or prefer a shorter tour, the Frozen Niagara Tour is a fantastic option. It’s less physically demanding and showcases some of the cave’s most beautiful formations, including the stunning flowstone formation that gives the tour its name.
• Green River Bluffs Trail: After exploring underground, stretch your legs on the Green River Bluffs Trail. This easy hike offers scenic views of the Green River and the surrounding bluffs, making it a great way to see the park’s above-ground beauty.
• Cedar Sink Trail: For a unique experience, hike the Cedar Sink Trail. This 1.5-mile loop takes you to a large sinkhole where you can see how the landscape interacts with the cave system below. It’s a peaceful and intriguing hike through dense forest.
• Visitor Center: Don’t miss the Mammoth Cave Visitor Center before you leave. It offers informative exhibits about the cave’s history, geology, and ecology.

Keep your eyes peeled for wildlife both above and below ground. The park is home to a variety of species, including deer, bats, and various birds. The Echo River Spring Trail is a good spot for birdwatching and possibly spotting other animals.

Where to Stay: Consider staying at the Lodge at Mammoth Cave for a convenient and comfortable place to rest. There are also several campgrounds within the park if you prefer a more rustic experience.

Day 20: Louisville, Kentucky

• Louisville Slugger Museum & Factory: Start your day with a visit to the Louisville Slugger Museum & Factory, where you can see how the famous baseball bats are made. The giant bat outside the museum is an iconic photo spot. Inside, you can take a tour of the factory, hold bats used by baseball legends, and even customize your own mini bat.
• Churchill Downs and the Kentucky Derby Museum: No visit to Louisville is complete without experiencing the legendary Churchill Downs. Home to the Kentucky Derby, this historic racetrack is a must-see. The Kentucky Derby Museum offers a fascinating look at the history and traditions of the Derby, and you can even take a guided tour of the grounds. If you’re visiting during racing season, try to catch a live race!
• Bourbon Trail: Louisville is the gateway to the Kentucky Bourbon Trail, and there are several distilleries in the city where you can sample some of the world’s best bourbon. Stop by Angel’s Envy, Old Forester, or Evan Williams for a tour and tasting. Even if you’re not a big bourbon drinker, the history and craftsmanship behind it are fascinating.

More Attractions

• Waterfront Park: Take a break and enjoy the outdoors at Louisville Waterfront Park. This scenic park along the Ohio River is perfect for a leisurely stroll, a bike ride, or just relaxing by the water. The Big Four Bridge offers great views and connects you to Indiana if you’re up for a longer walk or bike ride.
• Waterfront Park: Take a break and enjoy the outdoors at Louisville Waterfront Park. This scenic park along the Ohio River is perfect for a leisurely stroll, a bike ride, or just relaxing by the water. The Big Four Bridge, a converted railroad bridge, offers great views and connects you to Indiana if you’re up for a longer walk or bike ride.
• Muhammad Ali Center: Dive into the life and legacy of Louisville’s most famous son at the Muhammad Ali Center. The museum is more than just a tribute to Ali’s boxing career; it also explores his activism, humanitarian efforts, and impact on the world. It’s an inspiring stop that’s well worth your time.
• NuLu (East Market District): Louisville’s NuLu district is where old meets new. This revitalized area is full of art galleries, boutique shops, and trendy restaurants. It’s a great spot to grab lunch, shop for unique souvenirs, or just wander around and soak in the local vibe. Check out Please & Thank You for some of the best cookies in town.

If you’re looking to see this city in its most vibrant, I suggest you come in spring during the Derby season! The Kentucky Derby Festival, leading up to the race in early May, is packed with events, parades, and celebrations. It’s the perfect time to visit if you want to experience Louisville at its most vibrant.

Day 21: Indianapolis, Indiana

As your road trip winds through the Midwest, it’s time to head northeast for about two hours to Indianapolis, Indiana. Known as the “Racing Capital of the World,” Indianapolis is famous for the Indy 500, but there’s so much more to this dynamic city. The drive from Louisville to Indianapolis is straightforward, following I-65 N. Traffic in downtown Indy can get busy, especially during events, so plan your timing accordingly.

Here’s what to see and do in Indianapolis:

• Indianapolis Motor Speedway and Museum: Start your day with a visit to the iconic Indianapolis Motor Speedway. Even if you’re not a racing enthusiast, the Speedway Museum is a must-see, offering a deep dive into the history of racing and the legendary Indy 500. If you’re lucky, you might catch a practice session or take a lap around the track in a tour bus.
• White River State Park: This urban park is the perfect place to enjoy some green space in the heart of the city. You can rent a bike, take a paddleboat on the canal, or just stroll along the riverfront. The park is also home to several top attractions, including the Indianapolis Zoo and the Eiteljorg Museum of American Indians and Western Art.
• Massachusetts Avenue (Mass Ave): This vibrant arts and entertainment district is where you’ll find a mix of indie boutiques, art galleries, and great dining spots. It’s a great area to explore on foot, with plenty of street art, quirky shops, and delicious food. Grab a coffee at Coat Check Coffee or indulge in some local fare at The Eagle.
• Monument Circle: Climb to the top of the Soldiers and Sailors Monument for panoramic views of the city, or just relax and people-watch in this bustling area.

More Sights to See

• The Children’s Museum of Indianapolis: If you’re traveling with kids (or just young at heart), the Children’s Museum of Indianapolis is a must-visit. It’s the largest children’s museum in the world, featuring interactive exhibits on everything from dinosaurs to space exploration. Plan to spend a few hours here—it’s that good!
• Indianapolis Museum of Art at Newfields: For art lovers, a visit to Newfields is essential. The museum’s collection spans thousands of years, with everything from classic European paintings to contemporary art. The surrounding gardens and grounds are also worth exploring, especially during the warmer months.
• White River State Park: An urban oasis in the middle of the city, this park offers beautiful trails, green spaces, and access to top attractions like the Indianapolis Zoo and the Indiana State Museum.
• Indianapolis Museum of Art at Newfields: Explore a vast collection of art spanning centuries, plus beautiful gardens and outdoor sculptures. The 100 Acres Art and Nature Park is a hidden gem.
• Broad Ripple Village: A lively neighborhood with a bohemian vibe, Broad Ripple is known for its indie shops, diverse eateries, and vibrant nightlife. Great for a day of exploring or an evening out.
• Lucas Oil Stadium: Even if you’re not a football fan, a visit to this state-of-the-art stadium, home of the Indianapolis Colts, is impressive. Check out a game or take a behind-the-scenes tour.

Indianapolis has a thriving food scene with plenty of options. Try St. Elmo Steak House for a classic Indy experience or hit up Bluebeard for something more modern and eclectic. For breakfast, Café Patachou is a local favorite.

Additional Itinerary Suggestion: Cincinnati, Ohio

If you have an extra day or two, consider heading east from Indianapolis to Cincinnati, Ohio. It’s about a two-hour drive and totally worth it. Cincinnati, known as the “Queen City,” sits along the Ohio River and is famous for its historic architecture, vibrant arts scene, and unique culinary offerings—Skyline Chili, anyone?

While you’re there, take a stroll through the lively Over-the-Rhine neighborhood, visit the Cincinnati Art Museum, and catch a Reds game if you’re a baseball fan. The city’s riverfront parks offer stunning views, and the iconic Roebling Suspension Bridge is a must-see. It’s a great add-on to your Midwest road trip!

Days 22-23: Hocking Hills State Park, Ohio

Your road trip now takes you into the heart of Ohio’s natural beauty—Hocking Hills State Park. Just a little over two hours southeast of Cincinnati, Hocking Hills is a paradise for nature lovers! It offers stunning landscapes, dense forests, and dramatic rock formations. This park is a great spot to unwind and reconnect with nature after exploring the cities.

Top Attractions in Hocking Hills

• Old Man’s Cave: Start your visit with a hike through Old Man’s Cave, one of the most popular spots in the park. The trail winds through lush forests, past waterfalls, and under massive rock overhangs. The scenery here is absolutely breathtaking, so be sure to have your camera ready.
• Ash Cave: Another must-see, Ash Cave is the largest recess cave in Ohio. The easy, accessible trail leads you to this awe-inspiring natural wonder. You’ll see a cascading waterfall that’s particularly impressive after a good rain.
• Cedar Falls: For a bit more adventure, hike the trail to Cedar Falls. This waterfall is one of the most picturesque in the park, surrounded by towering cliffs and dense greenery. It’s a perfect spot to relax and enjoy the sounds of nature.
• Rock House: If you’re up for exploring a bit off the beaten path, head to Rock House. This unique cave, formed entirely of sandstone, has a cathedral-like feel with its high ceilings and “windows” carved out by erosion. It’s a little eerie but very cool to explore.
• Conkle’s Hollow: For a less crowded experience, take a hike at Conkle’s Hollow. The rim trail offers stunning views from the top of the gorge, while the lower trail keeps you shaded and close to the towering cliffs. Either way, it’s a peaceful and scenic hike.

For a truly unique experience in Hocking Hills, try visiting the park at dawn. The early morning light filtering through the trees creates a mystical atmosphere, especially at spots like Old Man’s Cave and Ash Cave.

Plus, you’ll have the trails almost entirely to yourself, making it a peaceful and serene way to explore the park before the crowds arrive.

If You Have Time: Cleveland, Ohio

Beyond the music, Cleveland has a cool downtown area with plenty of restaurants, shops, and attractions. Check out the West Side Market for local eats, or take a stroll through one of the most beautiful places in the Midwest, Cleveland Botanical Garden.

Days 24-25: Detroit, Michigan

Now it’s time to head up to Detroit, Michigan, about a three-hour drive northwest from Cleveland. Detroit, also known as the Motor City, is a place full of history, creativity, and a resilient spirit that’s led to an exciting cultural revival. Whether you’re into cars, music, or art, Detroit has something cool for you to explore.

Make sure to visit these places:

• The Henry Ford Museum of American Innovation: Start your visit with a deep dive into America’s industrial history at The Henry Ford Museum. It’s not just for car enthusiasts—this massive museum has everything from historic planes to the bus where Rosa Parks made her stand.
• Motown Museum: Don’t leave Detroit without visiting Hitsville U.S.A., where Motown legends like Stevie Wonder and The Supremes recorded their hits. The Motown Museum offers a fun, nostalgic look at the music that shaped a generation. You’ll get to see the original recording studio and hear some great stories from the guides.
• Detroit Institute of Arts: Art lovers should head to the Detroit Institute of Arts, home to an incredible collection that spans from ancient to modern art. Diego Rivera’s “Detroit Industry” murals are the highlight here, offering a powerful tribute to the city’s industrial roots.
• Eastern Market: For a taste of local life, explore Eastern Market, one of the oldest and largest year-round markets in the U.S. It’s packed with vendors selling fresh produce, flowers, and unique local goods. It’s also a great place to grab a bite from one of the food trucks or nearby restaurants.

Additional Spots to Visit

Days 26-27: Traverse City, Michigan

Next, it’s time to head up north to the charming town of Traverse City, Michigan, about a four-hour drive from Detroit. Nestled along the shores of Lake Michigan’s Grand Traverse Bay, Traverse City is the cherry capital of the world, famous for its annual National Cherry Festival that draws visitors from all over. This area is also one of the most productive wine regions in the Midwest, with its unique microclimate making it ideal for vineyards.

Here’s how to best spend your two days here:

• Traverse City Wine Trail: If you’re a wine lover, you’re in for a treat. Traverse City is home to over 40 wineries, most of them located on the scenic Old Mission and Leelanau Peninsulas. Spend an afternoon wine tasting and enjoying the stunning vineyard views. Some popular stops include Chateau Chantal, Black Star Farms, and 2 Lads Winery.
• Downtown Traverse City: Explore the heart of the city by wandering through its charming downtown area. You’ll find unique boutiques, art galleries, and plenty of great places to eat. Grab a coffee at Brew, or treat yourself to some locally made chocolates at Cherry Republic.
• Grand Traverse Bay: Get out on the water with a kayak, paddleboard, or even a boat tour of the bay. The crystal-clear waters of Grand Traverse Bay are perfect for a day of fun and relaxation. If you’re there in the summer, don’t miss the National Cherry Festival, a celebration of all things cherry that draws visitors from all over.
• The Village at Grand Traverse Commons: A former asylum turned into a lively hub with unique shops, art galleries, restaurants, and wineries. The historic architecture and surrounding nature trails make it a perfect spot for a leisurely day out.

More Spots to Explore

Day Trip Ideas: Sleeping Bear Dunes National Lakeshore & Mackinac City

If you’re up for a longer day trip, head about two hours north to Mackinac City. This charming town is the gateway to Mackinac Island, known for its historic forts, fudge shops, and the stunning Mackinac Bridge. While you’re in Mackinac City, you can explore Colonial Michilimackinac, visit the Old Mackinac Point Lighthouse, or take a ferry over to the island for a day of exploration.

Day 28: Grand Rapids, Michigan

As you make your way south, your next destination is Grand Rapids, Michigan, about a two-hour drive from Traverse City. Grand Rapids, often dubbed “Beer City, USA,” boasts more than just an impressive craft beer scene—it’s also a hub for art, culture, and history.

Situated along the Grand River, this city was once a major furniture manufacturing center, earning the nickname “Furniture City.”

Add these spots to your Midwest itinerary:

• Frederik Meijer Gardens & Sculpture Park: Start your visit with a trip to Frederik Meijer Gardens, one of the top cultural destinations in the Midwest. This expansive park features stunning gardens, a tropical conservatory, and an impressive collection of sculptures, including works by renowned artists like Rodin and Moore. The Japanese Garden is a particularly peaceful spot to explore.
• Downtown Market: For a taste of local flavor, head to the Downtown Market. This vibrant market is home to a variety of food vendors, offering everything from fresh seafood and artisan cheeses to gourmet chocolates and pastries.
• Grand Rapids Art Museum (GRAM): Art lovers shouldn’t miss the Grand Rapids Art Museum, which houses a diverse collection of art from the Renaissance to modern times. The LEED Gold-certified building itself is a work of art.
• Gerald R. Ford Presidential Museum: Learn about the life and legacy of the 38th President of the United States at the Gerald R. Ford Presidential Museum. The museum offers exhibits on Ford’s presidency, his early life, and significant events of the 1970s.
• Heritage Hill Historic District: Take a stroll through Heritage Hill, one of the largest urban historic districts in the U.S. This neighborhood is home to over 1,300 historic buildings, ranging from Greek Revival to Victorian architecture.

Tour Suggestion: Craft Beer Tour

Day 29: Starved Rock State Park, Illinois

As your road trip starts to wind down, make your way south from Grand Rapids to Starved Rock State Park in Illinois. The drive takes about three and a half hours, leading you to one of the Midwest’s most stunning natural areas. Nestled along the Illinois River, Starved Rock State Park is famous for its dramatic canyons, towering sandstone bluffs, and beautiful waterfalls.

• Hiking Trails: Starved Rock is a hiker’s paradise, with over 13 miles of trails that wind through canyons, forests, and along the river. The most popular trail takes you to the top of Starved Rock itself, where you’ll be rewarded with panoramic views of the Illinois River. Along the way, explore canyons like French Canyon and Wildcat Canyon, which are particularly stunning after a rain when the waterfalls are flowing.
• Waterfalls: The park is home to 18 canyons, many of which feature seasonal waterfalls. Some of the best spots to see these waterfalls include LaSalle Canyon, where you can walk behind the falls, and St. Louis Canyon, known for its picturesque setting. The best time to see the falls is in the spring or after heavy rainfall.
• Eagle Watching: If you’re visiting in the winter, you’re in for a treat. Starved Rock is a prime spot for eagle watching as these majestic birds gather along the river to hunt. The park offers guided eagle-watching tours, or you can grab your binoculars and head to the observation areas on your own.
• Starved Rock Lodge: After a day of hiking, take a break at the historic Starved Rock Lodge. Built in the 1930s, the lodge offers cozy accommodations, a restaurant with stunning views, and a welcoming atmosphere. Even if you’re not staying overnight, it’s a great place to relax and grab a meal.

What to See in Starved Rock State Park

• Wildcat Canyon: This is one of the tallest and most impressive canyons in the park, with a stunning waterfall that flows after rain. It’s a must-see, especially if you’re into photography.
• St. Louis Canyon: Known for its beautiful waterfall, this canyon is a great spot for a hike. The surrounding cliffs and lush greenery make it feel like a hidden oasis.
• French Canyon: One of the most popular canyons in the park, French Canyon features steep walls and a picturesque waterfall. It’s an easy hike from the Visitor Center and a great introduction to the park’s natural beauty.
• Eagle Cliff Overlook: For panoramic views of the Illinois River and the park’s canyons, head to this overlook. It’s a short hike up, but the views are totally worth it.
• Lover’s Leap Overlook: Another great vantage point, Lover’s Leap offers sweeping views of the Illinois River, and if you’re lucky, you might spot some bald eagles soaring above.

The Illinois River offers plenty of opportunities for boating and fishing. You can rent a canoe or kayak to explore the river up close, or cast a line and try your luck catching catfish, bass, and other local species. Boat rentals are available at the nearby marina.

Day 30: Return to Chicago, Illinois

Suggested Routes:

Stops Along the Way:

Once Back in Chicago:

Things to Consider When Planning Your Midwest Road Trip

Where to Start Your Road Trip

Chicago is the perfect starting point for your Midwest road trip, with different fun things to do. It’s a major transportation hub with plenty of flight options, making it easy for travelers from anywhere to fly in and rent a car. Plus, Chicago itself is a fantastic city to explore, offering everything from iconic landmarks and world-class museums to incredible food and vibrant neighborhoods.

If you’re looking for alternatives, consider Minneapolis for its artsy vibe and beautiful lakes or St. Louis for its historic charm and the Gateway Arch. Both cities are perfect launching pads with plenty of fun stuff to explore before you hit the open road.

Best Time of Year for a Road Trip in the Midwest

Number of Days for a Midwest Road Trip

Other Destinations to Consider When Road Tripping Through the Midwest

If you’ve got extra time and want to see even more of the Midwest, check out these awesome spots:

• Galena, IL: This charming town is known for its well-preserved 19th-century buildings, cute shops, and wineries. Perfect for a relaxing getaway.
• Door County, WI: A beautiful peninsula with stunning lake views, quaint villages, and outdoor activities like kayaking and hiking. Don’t miss the fish boils!
• Traverse City, MI: Famous for its wineries, cherry orchards, and gorgeous Lake Michigan beaches. It’s a great place to unwind and enjoy the scenery.
• Indianapolis, IN: Home to the Indianapolis Motor Speedway, cool museums, and a vibrant downtown. It’s a fun stop for racing fans and culture lovers.
• Mackinac Island, MI: Step back in time on this car-free island. Explore historic sites, ride a bike around the island, and indulge in some famous Mackinac Island fudge.

FAQs About the Midwest Road Trip

What does a 5-day Midwest road trip look like?

• Day 1: Chicago, Illinois: Kick things off in the Windy City. Explore iconic sites like Millennium Park, the Art Institute, and Navy Pier. Don’t miss a deep-dish pizza dinner!
• Day 2: Milwaukee, Wisconsin: Head north to Milwaukee. Visit the Milwaukee Art Museum, stroll along the Riverwalk, and tour a local brewery.
• Day 3: Madison, Wisconsin: Drive to Madison. Check out the Wisconsin State Capitol, walk around the UW-Madison campus, and relax at the Memorial Union Terrace by the lake.
• Day 4: Wisconsin Dells, Wisconsin: Spend a fun-filled day at the waterparks, take a scenic boat tour, and explore Mirror Lake State Park.
• Day 5: Return to Chicago: Head back to Chicago, stopping in small towns or scenic spots along the way. Enjoy a farewell dinner in the city.

What is the best route to take for a Midwest road trip?

How long does it take to drive through the Midwest?

Can you take a road trip through the Midwest in 7 days?

Absolutely! Here’s a sample 7-day itinerary:

• Day 1: Chicago: Explore the city’s rich culture and food scene.
• Day 2: Milwaukee: Dive into the city’s breweries and museums.
• Day 3: Madison: Enjoy the college town vibes and lakeside activities.
• Day 4: Wisconsin Dells: Have a blast at the waterparks and scenic tours.
• Day 5: Minneapolis: Discover the art and music scene in the Twin Cities.
• Day 6: Des Moines: Explore parks, markets, and local eateries.
• Day 7: St. Louis: End your trip with iconic sights like the Gateway Arch.

What kind of car is best for this trip?

Are there any tolls on the way?

Yes, there are tolls on some highways, especially around major cities like Chicago. Be sure to have cash or a credit card ready for toll booths. Using an I-PASS or E-ZPass can make the journey smoother. Also, keep an eye out for any specific road rules or permits needed in different states.

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