The Windy City is famed for its impressive architecture, museums, parks, the skyscraper-dotted skyline, and vibrant live music scene, which includes many jazz, blues, and rock clubs. It’s also becoming increasingly hip with lots of trendy neighborhoods worth exploring and cool street art telling local historic stories.
Chicago is also home to a growing collection of unique hotels from intimate boutiques to sleek high rises. Thinking of staying? Here are some of the best cool, unusual, and just simply beautiful hotels to stay in Chicago (in no particular order)…
1. theWit Hotel – a hip and very Instagrammable upscale hotel which offers fabulous city views and is perfect for partying Millenials and Gen Zs
A popular Chicago hotel on Tripadvisor and set in a striking glass building in the heart of Chicago’s theatre, arts, and shopping district, the 4-star exceptionally rated theWit Hotel features eye-popping design, stunning views, and creative culinary delights for you to enjoy during your stay.
Designed with elegance in mind, each of the trendy hotels’ smart and stylish guest rooms have their own look and personality and come with a wonderful spa-style bathroom, floor-to-ceiling windows, river views, flat-screen TVs, and iPod docks.
There are many chic and romantic hotels in Chicago but this DoubleTree by Hilton Hotel offers more than just overnight accommodation; it is a destination on its own right.
With a rooftop lounge offering fabulous views across the city, a private movie theatre, an onsite spa, and the delicious, innovative cuisine of the State and Lake Restaurant, The Wit is really quite a fabulous place to stay in the city.
- To book, check prices or availability for theWit Hotel
2. The Robey – a hip, trendy, and very Insta-worthy Chicago hotel located in a cool neighborhood
The exceptionally rated Robey Hotel is very trendy and swish! This iconic and upmarket Art Deco building is set in the heart of Chicago’s hippest neighborhood. You only need to step outside the main entrance to be deep into the streets of Wicker Park and Bucktown, the creative hub of the city.
Discover unsigned bands, boho chic, and vegan eateries on every corner if you can pull yourself away from the modern cool vibe of this hip Chicago abode.
Triangular suites – with plenty of tech, sleek wooden floors, custom furniture, and luxe linens – offer extensive views out across the city, whilst the fab rooftop terrace with its very own pool and Cabana Club cocktail bar means you can still feel tropical even here in the windy city.
Cable TV, free WiFi, and light and airy contemporary rooms come as standard in this uber-chic and very cool Chicago hotel. Wonderful!
- To book, check prices or availability for The Robey Chicago
3. Virgin Hotels Chicago – this hip modern hotel voted #1 Hotel by Conde Nast Reader’s Choice is a great place to party
One of the top-rated hotels on TripAdvisor, this is a trendy Chicago hotel with modern sophistication and truckloads of style. Located in Chicago’s Loop area in Downtown, travelers will be spoilt for choice with so many things to see and do right on their doorstep.
The cool hotel has an upscale ambience without feeling too highbrow, allowing guests to relax, have fun, and be themselves.
Communal areas and bedrooms have great attention to detail with plush furnishings and modern ornamental pieces. Like many hotels in the city, the Virgin Hotels’ Chicago has a chilled-out rooftop bar area with breathtaking views of the wider city.
Although closed during the heart of winter, warmer months see a DJ and lively crowd until the early hours – definitely one of the best four-star hotels in Chicago.
- To book, check prices or availability for Virgin Hotel Chicago
4. Hotel EMC2 – a unique, modern and creative hotel with striking industrial chic contemporary decor
This unique Chicago hotel which is part of the prestigious Autograph collection can be found close to the central Magnificent Mile Shopping District within the vibrant Streeterville neighborhood.
A beautifully decorated luxurious urban refuge, the 4-star, and very highly rated Hotel EMC2 perfectly capture the creative spirit of the city with interiors that are designed to sit at the intersection of art and science.
Think sumptuous velvet furnishings mixed with brass fitments and industrial lighting, dark wood floor, marble walls, and oversized artwork and you have captured the mood of the hotel’s eclectic styling.
The truly gorgeous modern/vintage rooms offer flat-screen TVs, minifridges, coffeemakers, funky glass-enclosed showers, and designer toiletries.
The highly regarded Albert restaurant is 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. Just fabulous darling!
- To book, check prices or availability for Hotel EMC2 Chicago
5. Moxy Chicago Downtown – a new, fun and funky hotel with a sociable vibe is a great choice for partying Millenials and Gen Zs
Moxy Chicago Downtown is a 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.
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.
- To book, check prices or availability for Moxy Chicago Downtown
6. Freehand – fun and funky reasonably priced Chicago accommodation housed in a historic 1927 building
Based in Chicago’s trendy River North neighborhood, Freehand Chicago is nearby central amenities and within easy access to all areas of the city.
The hotel is set inside a refurbished 1920s art deco building and among Chicago’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 plenty of 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 Chicago
7. Thompson Chicago – this dashing Gold Coast beauty is one of the best hotels to stay in Chicago
Chicago’s affluent Gold Coast is full of upscale restaurants and historic mansions and nestled in amongst them (very near Michigan Ave and The Magnificent Mile) is this sophisticated Chicago abode.
The 4-star exceptionally rated Thompson Hotel is 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.
This luxury Chicago boutique hotel offers bedrooms that ooze style, with floor-to-ceiling windows affording fantastic views out across the famous Chicago skyline as well as all the usual mod cons such as high-thread-count sheets, and flat-screen TVs, and rainfall showers.
One of the hottest eateries in the city, Nico Osteria is situated in the hotel, and if you can book a table you are in for a treat.
One of the best and largest hotels in Chicago, you can also enjoy drinks and cocktails at the smart Salone Nico, one of Chicago’s most popular downtown wine bar 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 Chicago
8. Chicago Athletic Association – a unique hipster’s paradise set in an 1890s Gothic building that once housed an exclusive sportsmen’s club
Situated in Chicago’s Downtown area overlooking Michigan Avenue, the Chicago Athletic Association is arguably one of the best-located and coolest hotels in the city.
The hip Chicago hotel makes an instant impression with its gothic architecture, low lighting, a variety of classic furniture, and its sporty past connections.
The interior of communal areas feels 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! Easily one of the coolest and nicest hotels in downtown Chicago.
- To book, check prices or availability for The Chicago Athletic Association
9. Selina Chicago – a funky, arty and sociable hotel located in Near North Side
Selina hotels are the ultimate hipster hotels with everything necessary for life and work for digital nomads, such as co-working spaces, shared kitchens, event and meeting spaces, library, spa, yoga sessions and bike and scooter rentals.
At Selina Chicago, this comes with a premium location in the heart of the city, close to the Magnificent Mile, stores, restaurants, and Oak Street beach.
The rooms are done in restful shades of cream, for an oasis of calm amid the noise of the city. 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 Chicago’s golden years.
You’ll find a wide range of restaurants in the nearby Magnificent Mile and there’s a grab-and-go option for breakfast as well to start off your day just right.
- To book, check prices or availability for Selina Chicago
10. The Kimpton Gray Hotel – a beautiful upscale boutique hotel with an Art Deco-themed design
Set in one of Chicago’s finest landmarks and top hotels, the 4-star very highly rated Kimpton Grey is the height of opulence, offering smart, sophisticated, and stylish Art Deco-inspired accommodation throughout.
The ornate high-rise building dates from 1894 and the trendsetting Chicago hotel is just is a 12-minute walk from central Millennium Park and offers some of the finest views you can find in the city.
With quirky amenities on offer 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 hotel.
Just an all-around beautiful place to stay in the city and one of the best luxury Chicago hotels.
- To book, check prices or availability for Kimpton Grey Chicago
11. The Hoxton – a trendy and creative club-style boutique hotel from the popular European hotel brand
The creative and very popular trendy European brand brings its own brand of style to downtown Chicago 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 Hoxton Hotel Chicago 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.
Hotel highlights include chic and vintage/retro-inspired guest rooms with floor-to-ceiling windows, mini-fridges, coffee makers, flat-screen TVs, and free Wi-Fi, a hip bar and lounge, two restaurants, a co-working space, an intimate cocktail bar, and a cool outdoor rooftop pool accompanied with an eatery and bar offering great city views.
- To book, check prices or availability for The Hoxton Hotel Chicago
12. Talbott Hotel – a popular trendy boutique hotel located on the Magnificent Mile
Just a few short steps away from the iconic Magnificent Mile on Michigan Avenue, the 4-star exceptionally rated Talbott Hotel offers well-appointed rooms and effortless style throughout.
Opulent interiors combine retro chic with industrial touches, whilst the elegant rooms at this cool and unusual Chicago stay are well thought out and full of modern conveniences including free Wifi, widescreen TV’s as well as 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, offering 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 don’t miss the chance to eat alfresco on the streets of Chicago in the hotel’s beautiful patio area! Sublime!
- To book, check prices or availability for The Talbott Hotel
13. The Gwen – a prestigious, trendy and unique Chicago hotel that exudes the vintage glamour of Chicago’s 1930s
A Luxury Collection Hotel Member and once voted one of the best luxury hotels in Chicago by Travel and Leisure, this place is really something else.
From the breathtaking Art Deco lobby through to the first-floor limestone panels carved by Chicago-born acclaimed sculptor Gwen Lux, this chic and trendy Chicago hotel is truly a vision to behold!
Just a few short steps from central Michigan Avenue with its collection of shops, restaurants, and bars, you will be sleeping in the heart of the city.
With brass features and fittings, the 5-star exceptionally rated Gwen Hotel has rediscovered its 1930s origins and the theatrical styling is displayed throughout the hotel in intricate detail.
The upscale stylish bedrooms all invoke the sumptuous styles of the Deco period but are combined with a range of modern conveniences including luxury toiletries, Keurig coffeemakers, free Wi-Fi, and enormous wall-mounted TV’s.
Other fabulous amenities include a sophisticated restaurant, a terrace bar offering superb city views, a gym, and a very grand lobby lounge. A much-loved Chicago institution and one of the best Chicago 5-star hotels!
- To book, check prices or availability for The Gwen Hotel Chicago
14. 21c Museum Hotel – a new cool downtown hotel which is part hotel, part art gallery
At the 21c Museum Hotel in Chicago, contemporary art is part of the decor and there are also curated exhibitions and cultural programming for travelers and local residents, making it a cultural hub in itself.
The location in Chicago’s Magnificent Mile puts you close to everything downtown including the shopping at Michigan Avenue, Millennium Park and the city’s famous museums.
The rooms designed by the architectural firm of Deborah Berke Partners have clean, contemporary lines and luxurious furnishings in quiet neutral shades.
There are 297 rooms and 106 suites where guests can find a quiet retreat to prepare for the next day’s adventures in the Windy City. Those in need of extra pampering can book an appointment at the Soothe spa.
The Lure Fishbar offers the finest seafood along with a fresh bar and also has the option of in-room dining.
- To book, check prices or availability for 21c Museum Hotel
15. Viceroy Chicago – a beautiful upscale design located in an art deco tower in the chic Gold Coast Historic District
Viceroy hotels are known for their reimagining of traditional luxury and in Chicago that means a retro-chic hotel located in the upscale Gold Coast neighborhood, right on the shores of Lake Michigan.
The glass-fronted building at Viceroy Chicago 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.
The rooms are luxurious and well-appointed, and when you’re ready for some fine dining and nightlife, you can head to the rooftop Devereaux Lounge, or to the Somerset for classic American food and country club style.
- To book, check prices or availability for Viceroy Chicago
16. Hotel Julian Chicago – a cool and stylish contemporary hotel located in the vibrant Loop neighborhood
The intriguing mix of traditional elegance with high ceilings and light-filled interiors and quirky contemporary decor and art speak to the innovation and dynamism of the city.
The spacious rooms also feature lofty ceilings, luxurious linens, Nespresso machines and state-of-the-art 55-inch Smart televisions. Amenities include a fitness center and a laundry service.
With all the culinary choices of the Magnificent Mile right outside, the on-site About Last Knife Steak Bar holds its own, combing edgy decor with a classic menu and a lively cocktail bar.
- To book, check prices or availability for Hotel Julian Chicago
17. The Blackstone Hotel – immaculate classic elegance and a beautifully unique upscale place to stay in Chicago
An architectural icon with a legendary past, the 4-star exceptionally rated Blackstone Hotel which is part of the prestigious Autograph collection is located on the Cultural Mile and opposite Grant Park in Down Town Chicago.
Housed in a fabulous 1910 beaux-arts building and offering a one-of-a-kind experience for travelers with taste, a stay at the Chicago Blackstone Hotel is an opportunity to explore Chicago’s former “Hotel of Presidents”.
Every room is completely unique and offers sumptuous sleeping accommodations complete with Wifi, iPod docks, and flat-screen TVs as well as some with gorgeous lake views.
The trendy Chicago accommodation is also home to over 1,600 contemporary artworks that are a feast for your eyes, swish club rooms, a gym, and the onsite Mercat a la Planxa restaurant which earns rave reviews for its upscale tapas menu, excellent wines, and upbeat atmosphere as well as craft cocktails with an original 1960s vibe. This place will envelop you in so much elegance you won’t want to leave!
- To book, check prices or availability for The Blackstone Hotel
18. Hotel Zachary – a chic and classy boutique hotel which embraces Chicago’s unique history and style
Chicagoans love their home teams and the Hotel Zachary, named for architect Zachary Taylor Davis who designed Wrigley Field, shows just how much. Many rooms and suites have Wrigleyville views, and the boutique hotel feels like an extension of the ballpark, with references to baseball history throughout and live streams of home team games.
The hotel’s decor embraces the style that defines Chicago hospitality, combining a clean modernist aesthetic with solid comfort. The rooms likewise have comfortable, even fluffy furnishings, plush robes, comfy chairs that add a touch of soothing color, hardwood flooring and rain showers for a personal spa experience,
When it’s time to eat, you can relax with a drink and a classic meal at The Bar at Hotel Zachary or stop off for a bite at the West Town Bakery coffee house.
- To book, check prices or availability for Hotel Zachary
19. Sophy Hyde Park – a new luxury Hyde Park boutique hotel located in Hyde Park with a striking and creative design
Quirky, creative and curious, Sophy Hyde Park is located near the city’s cherished institutions of science, industry and the arts.
The University of Chicago, McCormick Place Convention Center, Frank Lloyd Wright’s Prairie-style Robbie House and The Museum of Science & Industry are all nearby, and their presence can be seen in the boutique hotel’s design, decor and artwork.
The artwork in the hotel, curated by Karen Maki of Chicago Art Sources! is the product of a conversation with the local artists, the community and the city’s history that began during the construction phase.
The rooms are havens of luxury with plush lounge seating, hardwood floors, marble-tiled bathrooms and plenty of power outlets. Guests can enjoy a delicious meal at the Mesler Kitchen, which also offers seasonal open-air dining in The Sanctuary.
- To book, check prices or availability for Sophy Hyde Park
20. The Versey – a fun, quirky and reasonably priced hipster boutique hotel located in vibrant Lincoln Park
The Versey offers a great budget option for those looking to explore the city. Situated in the central Lincoln Park neighborhood in downtown Chicago, a wealth of restaurants, bars, excellent music venues, and boutiques are located right on your doorstep.
With small, but perfectly formed, clean and well-styled funky bedrooms, free Wi-Fi and passes to the nearby LA Fitness gym, this colorful and modern functional highly rated hotel offers fuss-free accommodation for those looking to spend their cash elsewhere during their stay.
The Chicago-themed art on the walls, and the brightly colored lobby with its maps and murals, sports memorabilia and records will inspire you to get out there and explore the Windy City for yourself!
- To book, check prices or availability for The Versey Chicago
21. ACME Hotel – a fun, quirky and funky themed hotel full of tech perfect for Millennials and Gen Zs
The exceptionally rated Acme Hotel enjoys a fabulous location the trendy central River North neighborhood (7-minute walk from shops along the Magnificent Mile), surrounded by wine bars, gastropubs and fancy boutiques galore, this hip alternative boutique hotel in Chicago is just a five-minute walk away from the shopping haven of Michigan Avenue.
With a bohemian feel, this unique and funky Chicago hotel oozes quirky indie-cool and is dotted with buzzing neon signs, graffiti-painted stairwells, and a lift with walls made of classic album covers.
Perfect for urban hipsters of all ages, the cool hotel even provides cool but comfy, tech-savvy bedrooms with free Wi-Fi, well-being chairs, wireless sound systems, and smart TVs. You can even rent Apple watches and Google Glasses to use during your stay – now that’s attention to detail!
When you are done exploring, settle down and relax in the hot tub, with a craft cocktail at the bar or even grab a pastry at the onsite bakery – a cool and funky city oasis!
- To book, check prices or availability for Acme Hotel
Some more of the best hotels to stay in Chicago…
- Peninsula Chicago – one of the most luxurious hotels in Chicago and where the celebrities stay in when they’re in town.
- Nobu Hotel – a serene oasis of Japanese minimalism and a great option for a gorgeous luxury Chicago hotel.
- Ritz-Carlton – one of the best five-star hotels in Chicago which is highly rated on Tripadvisor.
- The Hotel at Midtown – an upscale resort perfect for a Chicago Staycation.
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Blackstone Hotel images are copyright of Blackstone hotel.
My first true adventure began as a six month voyage around South East Asia as a fresh faced backpacker and ever since I’ve lived a semi nomadic existence, clocking up visits to over 40 countries. I’m a lover of US Road Trips, deserted beaches bathed in warm glow of a sunset, Cuban mojitos, travel destinations far away from the tourist crowds and all things Scandinavian – from cloudberry liquors to Nordic noirs. When not wandering the world and running Global Grasshopper, you’ll find me walking my rescued Greek street dog in leafy South West London, strolling around the Brighton Lanes on random day trips, hunting for photogenic landscapes or daydreaming about my favourite places; Havana, Copenhagen, Italy, Laos, California and the surreally beautiful landscapes of a wintry Iceland.