Chicago is famed for its impressive architecture, hip neighborhoods, skyscraper-dotted skyline, vibrant live music scene, and incredible collection of creative places to stay! From intimate boutiques to sleek high rises, here are some of my favorite spots in the Windy City…
1.theWit Hotel
This place wowed me! I discovered it housed in a striking glass building and inside it was a contemporary and striking design haven with lashings of glass which let in huge swathes of light, trendy, eclectic decor with splashes of bold colors, contemporary art installations, and retro-chic furniture. I found the vibe was playful but still sophisticated and luxurious – it felt like a unique modernist oasis in the heart of the city!
My sleek and stylish guest room came with an individual design with floor-to-ceiling windows, incredible city views, a large plush bed, a flat-screen TV, a coffee maker, air con and a large and very impressive ensuite bathroom with a large soaking tub for relaxation, designer toiletries a bathrobe and more incredible city views!
I found it nestled in the heart of the city’s theater district so I had iconic theaters, cultural attractions, shopping on the Magnificent Mile, and multiple excellent dining options all on my doorstep!
I also made sure I made use out of the private movie theatre, luxurious full-service spa, state-of-the-art gym and the chic rooftop lounge which served up handcrafted cocktails and wood-fired pizzas! On my last night I dined at the onsite State and Lake Tavern overseen Chef Michael Tauss which had a gastropub-style American cuisine menu and a chilled atmosphere!
2. The Robey
I was a big fan of this Insta-worthy spot! I found it set in a striking Art Deco building and inside I discovered light-filled interiors that beautifully mixed sleek modern designs with vintage accents, featuring soft, natural textures, clean lines, and industrial-chic details and lots of terrazzo and natural woods in a palette of red, pink, white, and gray.
My guest room featured a trendy industrial-chic design with custom-designed furniture, hardwood floors, luxurious linens, and floor-to-ceiling windows where I gazed at the sweeping views of the cityscape.
I really liked its location which was ideally situated in the heart of Wicker Park, a hip neighborhood which had a lively arts scene, boutique shopping, and a fine array of boho-styled bars and restaurants – it felt like a genuine local Chicago experience!
I also enjoyed its modern American breakfast, its onsite cozy café, The Cabana Club which had an incredible rooftop pool and terrace complete with lots of comfy sofas to lounge around in, the cocktails on the second-floor Lounge and I thought the exclusive access to live music performances in the bustling Wicker Park area was a nice touch too!
3. Virgin Hotel
I thought this party-hotspot was a fun option! Catering to a trendy crowd, I found a large high-rise hotel with a historic Art Deco façade and inside I found stylish and eclectic decor, with lashings of bold colors, contemporary art and plush velvet sofas. The vibe was upscale but playful and had a youthful spirit which I really loved!
My guest room featured a light but cozy Scandi-chic design, custom-made retro-chic furniture, a hipster-friendly large red Smeg fridge, a minibar stocked with street-priced snacks, plenty of work-space, a patented and very comfortable bed, ample workspaces, a minibar stocked with street-priced snacks, a flat-screen TV and a sliding privacy door that separates the dressing area from the sleeping space – it felt like a home away from home!
I found myself based in an awesome location in the Loop, where I had direct access to cultural and business hubs, including the Theater District, Millennium Park, and the Magnificent Mile.
I also thought the live DJs, the stylish rooftop bar (which had really incredible city views), cute little coffee shop and state-of-the-art fitness center was a great addition as well as the Commons Club restaurant which served up contemporary American cuisine with global influences in a trendy and open setting!
4. Hotel EMC2
This place was just so striking! I discovered a sleek, glass high-rise with an extraordinary avant-garde design and inside I found the interiors were equally as interesting the theme mixed the worlds of art and science and there was an eclectic mix of both modern art and vintage scientific instruments. There were velvet furnishings, brass fitments, industrial style lighting, dark wood floors, marble walls, and lots of oversized artwork!
My gorgeous guest room featured a boutique vintage-chic decor an extra-large luxurious bed complete with a cool action gel memory foam mattress, unique art pieces, organic toiletries, a flat-screen TV, a designer coffeemaker and organic toiletries.
I found it located in the vibrant Streeterville neighborhood, just steps away from the Magnificent Mile and Northwestern University’s downtown campus so I was in within walking distance of awesome shopping, dining, and superb cultural attractions.
I also really loved its other cool features which included a state-of-the-art fitness center, and the Albert, a dining experience where art and science converge in a menu inspired by global flavors and innovative culinary techniques.
The highly regarded Albert restaurant was a feast for the mind, body, and soul and is the perfect place to enjoy the delights of one of the finest hotels in the city. I thought it was just fabulous darling!
- To book, check prices or availability for Hotel EMC2
My personal highlights…
- The incredible robot butlers who were named Cleo and Leo – I saw them independently maneuver through the hotel’s hallways and even use the elevators to deliver items for us. I ordered food and drinks but I also saw them deliver towels and toiletries.
5. Moxy Downtown
I totally fell for this lively, quirky hotel right in the heart of the River North neighborhood, close to Millennium Park, art galleries, nightlife, restaurants, and more.
Like the other Moxy hotels, it is geared to millennial tastes and needs and the rooms have an abundance of USB and power outlets and 49-inch Smart TVs for all streaming needs.
In my opinion the vivid artwork in the shared spaces makes this an Insta-worthy hotel perfect for Millennials and Gen Zs. You’ll find more material sustenance at the 24-hour Zombie Taco and custom cocktails at Bar Moxy.
The rooms are comfortable with a restful, muted decor and many have city views. Inner Circle rooms overlook a quirky art installation inspired by the Garden of Eden.
6. Freehand
Based in the trendy River North neighborhood, I was a big fan of this boutique gem, which is near central amenities and easily accessible to all areas of the city.
The hotel is set inside a refurbished 1920s art deco building and among the city’s numerous Downtown skyscrapers and high-rises. There’s a stylish, relaxed vibe with modern touches to give extra color and warmth.
Tastefully decorated communal spaces and rooms of different sizes give tribute to America’s Midwest heritage. An award-winning cocktail bar called Broken Shaker is well worth visiting for exotic cocktails, light bites, and fun and games. A fitness center, cheap parking, and a coffee bar are some additional popular amenities.
- To book, check prices or availability for Freehand
7. Thompson
The city’s affluent Gold Coast is full of upscale restaurants and historic mansions and nestled amongst them (very near Michigan Avenue and The Magnificent Mile) is this sophisticated spot.
It’s also just a short distance from Lake Michigan and the loft-like, urban interiors have been designed by British design icon Tara Bernerd who has combined industrial fittings with warm woods and mid-century Americana.
My bedroom oozed style, with floor-to-ceiling windows affording fantastic views out across the famous city skyline. It also had all the usual mod cons, such as high-thread-count sheets, a flat-screen TV, and lush rainfall showers.
One of the hottest eateries in the city, Nico Osteria, is located in the hotel. I suggest booking a table if you can!
I also enjoyed drinks and cocktails at the smart Salone Nico, one of the city’s most popular downtown wine bars and cocktail lounges. Think it can’t get any better? They even throw in a complimentary luxury car service – not bad at all!
- To book, check prices or availability for Thompson
8. Chicago Athletic Association
Situated in the Downtown area overlooking Michigan Avenue, this is arguably one of the best-located spots in the city! This place made an instant impression on me with its gothic architecture, low lighting, a variety of classic furniture, and its sporty past connections.
To me, the interior of communal areas felt like an upscale English mansion house: upmarket yet comfortable, featuring tasteful wood paneling and fascinating floor tiling, giving a historic and elegant vibe.
The unique bedrooms mirror the traditional clubrooms of athletic associations and provide plenty of comfort for weary travelers.
A rooftop bar lets guests see fantastic views of Millennium Park and the wider city. Head to the Drawing Room to relax with afternoon tea or coffee next to a warm and cozy fireplace!
9. Selina
In my opinion, Selina hotels are the ultimate hipster hotels. They offer everything necessary for digital nomads’ lives and work, such as co-working spaces, shared kitchens, event and meeting spaces, a library, spa, yoga sessions, and bike and scooter rentals.
It has a premium location in the heart of the city, close to the Magnificent Mile, stores, restaurants, and Oak Street Beach.
My room came with restful shades of cream for an oasis of calm amid the city’s noise. Guests have the option to share rooms with bunk beds as well. The decor in the public spaces is an intriguing mix of contemporary minimalism with the grand traditions of the city’s golden years.
I also found a wide range of restaurants on the nearby Magnificent Mile, and there’s a grab-and-go option for breakfast, which helped when I was eager to explore!
10. The Kimpton Gray Hotel
Set in one of the city’s finest landmarks and top hotels, the 4-star spot is, in my opinion, the height of opulence. It offers smart, sophisticated, and stylish Art Deco-inspired accommodation throughout.
I loved the ornate high-rise building, which dates from 1894. It is just a 12-minute walk from central Millennium Park and offers some of the finest views in the city.
With quirky amenities like loaner bikes, nightly wine socials, and a yoga mat in every room, you will be staying in a cleverly crafted luxury environment.
The rooftop lounge serves light bites and refreshments, and the day spa, salon, and fitness centers offer all the complimentary facilities you would expect from such an upmarket place!
11. The Hoxton
The creative European brand brings its style to downtown, which is only a few minutes’ walk from Morgan Station and great restaurants and shops.
Housed in an industrial brick warehouse, the inside of the pet-friendly abode is a beautifully chic and artful haven with a club-style vibe and gorgeous features such as potted greenery, communal tables, and design elements fashioned by local artists.
My hotel highlights included my chic and vintage/retro-inspired guest room with floor-to-ceiling window, mini-fridge, coffee maker, flat-screen Ts, and free Wi-Fi.
There is also the hip bar and lounge, two restaurants, a co-working space, an intimate cocktail bar, and an outdoor rooftop pool accompanied by an eatery and bar offering great city views!
12. Talbott Hotel
Just a few short steps away from the iconic Magnificent Mile on Michigan Avenue, I was a big fan of how it offers well-appointed rooms and effortless style throughout!
Opulent interiors combine retro chic with industrial touches, whilst my elegant room was well thought out and full of modern conveniences, including free Wi-Fi, a widescreen TV, and Italian linens.
Upgraded rooms come with Apple Mac Mini computers and soaking tubs. Enjoy a drink or two in the contemporary chic hotel restaurant 20 East, which offers a thoroughly modern take on traditional American fare and a wide selection of craft beers.
You can always work off those extra calories in the onsite fitness center. Also, I would suggest not missing the chance to eat outside on the patio area! Sublime!
13. The Gwen
I thought this place was something special! From the breathtaking Art Deco lobby to the first-floor limestone panels carved by locally-born acclaimed sculptor Gwen Lux, this place won me over!
I also loved that it was a few short steps from Central Michigan Avenue with its collection of shops, restaurants, and bars. With brass features and fittings, the 5-star spot has rediscovered its 1930s origins, and the theatrical styling is displayed throughout the hotel in intricate detail.
My upscale, stylish bedroom came with a sumptuous style of the Deco period but combined with a range of modern conveniences, including luxury toiletries, a Keurig coffeemaker, free Wi-Fi, and an enormous wall-mounted TV.
Other fabulous amenities include a sophisticated restaurant, a terrace bar offering superb city views, a gym, and a very grand lobby lounge.
14. 21c Museum Hotel
I loved that contemporary art is part of the decor in this stylish spot there are also curated exhibitions and cultural programming for travelers and residents, making it a cultural hub in itself!
Its location on the Magnificent Mile put me close to everything downtown, including the shopping at Michigan Avenue, Millennium Park, and the city’s famous museums.
My room was designed by the architectural firm of Deborah Berke Partners and has clean, contemporary lines and luxurious furnishings in quiet, neutral shades.
There are 297 rooms and 106 suites and I could always find a quiet retreat to prepare for the next day’s adventures in the Windy City.
For those in need of extra pampering, I would suggest booking an appointment at the Soothe Spa. The Lure Fishbar offers the finest seafood and a fresh bar and has the option of in-room dining.
15. Viceroy
Viceroy hotels are known for reimagining traditional luxury, and in this city, that means a retro-chic hotel located in the upscale Gold Coast neighborhood, right on the shores of Lake Michigan.
In my opinion, the glass-fronted building looks like Art Deco redone for the 21st century, and the theme is echoed in the interior gold and black accents.
The decor is mid-century modern glamour, redone by renowned designers and architects Kelly Wearstler, Inc., Jean-Michel Gathy, and Wimberly Allison Tong & Goo, with a backdrop of floor-to-ceiling windows with views of the city and the lake.
My room was luxurious and well-appointed, and when you’re ready for some fine dining and nightlife I would highly recommend heading to the rooftop Devereaux Lounge, or the Somerset for classic American food and country club style.
