The Hotel Guru
17 Cool Hotels in Chicago

17 Cool Hotels in Chicago

Chicago has many draws for a fun city break. Whether you're visiting to catch a sports game, you're here for one of its festivals, or you're visiting simply to soak in the iconic architecture and experience the happening nightlife — there is a lot to keep busy with here. The hotel scene is as dynamic as the city itself. Expect grand and historic buildings converted into chic boutiques, sleek modern hotels with rooftop pools, and properties that have stand-out bars or restaurants. Our hotel experts have scanned the city to bring you a collection of cool hotels in Chicago selected on their design, amenities, and overall vibe. With something to suit most tastes and budgets, why not browse through our collection to start planning your stay?

For a rooftop pool

The Robey is a modern boutique hotel set in a striking art-deco building in Wicker Park. Pick this property for the chic whitewashed rooms (many of which have epic city views) and the French-American restaurant. However, the real lure is (obviously) the rooftop pool and bar.
The Hoxton Chicago is a hip luxury choice perfectly blending industrial and retro design. Expect vast rooms, high ceilings, polished concrete, and velvet upholstery. With a rooftop pool and a range of restaurants — this property won't fail to impress.

For the design

TheWit Hotel is a playful and buzzy hotel with spacious rooms and luxury creature comforts. Expect high ceilings, large windows with skyline views and bold flashes of colour all around. Dine at the excellent on-site restaurant and enjoy the 27th-floor rooftop bar.

For a glamorous stay

The Talbott Hotel is a glamorous Great Gatsby style hotel, in a beautifully refurbished 1920's building in downtown Chicago. The comfortable and spacious rooms have been carefully crafted by local designers. The popular on-site restaurant draws crowds, as do the cocktails at the vintage bar. An elegant choice.

For families

Freehand is a great value hotel with a boutique feel in downtown Chicago. Rooms are boho chic and come in various sizes including quads and a penthouse, which sleeps up to six, meaning there are flexible options for families. For those of age, there is a popular cocktail bar. With doubles starting at $85 (quads are just $25 per bed) — this is an affordable and hip choice for those travelling with kids.
Expect cool, contemporary city-style near Chicago's river and lakefront at the Loews Chicago. Rooms are sleek and modern with floor-to-ceiling windows to take in the city views. The rooftop bar and steak house are a real lure, while kids are well taken care of with iPads loaded with age-appropriate games, consoles, toys and activity books. Seriously good value for what is a luxury stay.

For a lively stay

Moxy Chicago Downtown is a buzzing and fun boutique-style hotel. When the reception doubles as a bar you can be sure of a good time! Decor is contemporary industrial-cool, with splashes of hot pink. Rooms aren't huge but have everything you need. The 24-hour taco restaurant is useful after nightly DJ sets. Perfect for party animals.
Lively Thompson Chicago is a converted mansion with a fabulous city centre position right beside Magnificent Mile. Stylish, contemporary, and with an acclaimed Italian restaurant and trendy bar — this well-priced downtown stay is an alluring choice.

For city style

Once the tallest building in the city, The Blackstone is a historic grand dame updated to the 21st Century. Expect wood-panelling, chandeliers and double-height ceilings combining with buzzing restaurants, an extensive art collection and quirky modern furniture. Having hosted many Presidents and celebrities, you can be sure of a very trendy crowd.

For a boutique

Ace Hotel Chicago was once a cheese factory but is now a hip boutique hotel. Highlights include city views, trendy co-working space and the buzzing outdoor rooftop. Rooms in this concrete and glass industrial conversion come with grey palettes, tiled bathrooms, local artwork and Bauhaus style furniture. Where the cool kids stay.
Hotel Zachary is a lively boutique hotel opposite Wrigley Field baseball stadium. An industrial conversion masterclass, interiors are cool, contemporary and yet cosy. Dining spaces are the real draw and popular with locals.
The Publishing House is a stylish boutique B&B set in a 110-year-old brick building with a literature theme. Complete with a heaving library and author-themed rooms, this is geek-chic territory. Breakfasts are home-cooked and there is a pantry available for guests all day.
Hotel EMC2 is a funky boutique-style hotel set in Chicago's lakeside neighbourhood. Pick this property for the bold design which includes rooms with Dali-esque murals, glass showers with copper tubing, dark wood floors and bright art. Complete with a lively restaurant and bar — this is a stylish yet fun stay.
The Gwen has undergone a divine transformation from historic building to luxury boutique hotel. Art Deco glamour reigns supreme in the rooms, restaurants and the chic wrap-around rooftop bar. Expect jewel tones, gold fittings, glossy marble and epic city views. A sexy and stylish stay.

For luxury

Chicago Athletic Association was a Gentleman's club in the early 1800s which has now opened its Venetian Gothic doors to all and boasts large, retro rooms with Millennium Park views. Cherry Circle Room catches the essence of its former dining glory while the rooftop bar completes the picture on this old-school-cool stay.
Kimpton Gray Hotel is an iconic and elegant building in the Loop's financial corridor. Named for its grey marble exterior, the rooms mirror this toned down grandeur, with the odd splash of colour and quirky design. With a range of bars and restaurants (including a hip roof terrace option), they have all the bases covered.

For an apartment

The Guesthouse Hotel comprises fully-equipped one, two and three-bedroom self-catered apartments in the Anderson District. Each of the fresh, lofty and spacious units provides everything expected from a lovely home; dishwashers, driers, gym, balconies and even a roof terrace. A chic option for long stays.

Still not sure where to book?

Browse our list of the best places to stay in Chicago.
Check out all our recommendations in Illinois.
Refine your search and look at the best hotels in West Loop, Chicago, the best hotels with rooftop pools in Chicago, the best five-star hotels in Chicago or the top Chicago hotels with parking.
Alternatively, you could contact one of our friendly Gurus for personalised advice.
- The Robey Chicago 89 rooms from £105
  
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  City Style  -  Chic accommodation in a historic building evoking memories of bygone years
  Local exploring  -  Make the most out of The Robey's location to truly get to know Chicago
  Sights nearby  -  Head over to Wrigley Field and enjoy a Cubs game or give the Lioncoln Park Zoo a visit
  Views  -  For great views book either a Corner Suite or Panorama Suite
  Recommended by  -  Tablet
  
  Situated in Chicago's Wicker Park, The Robey is set in the art-deco former Northwest Tower building and provides boutique, upmarket accommodation. Expect fresh and contemporary design. Café Robey serves up French-American fusion cuisine and cocktails are served on the rooftop lounge. Superb! See More
  
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- The Hoxton Chicago Chicago (Fulton Market) 182 rooms from £140
  
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  City Style  -  Offering a sophisticated and stylish air in an exciting, gourmet neighbourhood a short journey from the city centre
  Business meetings  -  The hotel boasts excellent meeting facilities and rooms perfectly suited for the travelling businessperson
  Local markets  -  Fulton Market takes its name from the world class food markets and dining in the area
  Sights nearby  -  The Oprah Winfrey show is filmed at the nearby Harpo Studios, a popular attraction
  
  A high-end luxury hotel in easy reach of the city centre and Chicago’s best nightlife spots, ideally designed and equipped for business or pleasure. Public spaces and rooms are bright and elegant, making excellent use of space, and the rooftop pool and range of restaurants won't fail to impress. See More
  
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- theWit Hotel Chicago 310 rooms from £154
  
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  City Style  -  A reminder of how fun city hotels can be. Stay here for a real feel of Chicago's bright lights
  Great walks  -  It's a very short walk to Grant Park. Visit Millenium Park with its famous Cloud Gate sculpture
  Spa  -  Spa@TheWit offers a range of treatments and massages
  Views  -  Great views from hotel
  
  Bright lights in the big city. Playful and buzzing hotel with spacious rooms and luxury creature comforts. Expect high ceilings, large windows with skyline views and bold flashes of colour all around. Dine at the excellent on-site restaurant. The 27th-floor rooftop bar is a reason to stay in itself. See More
  
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- The Talbott Hotel Chicago 149 rooms from £132
  
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  City Style  -  This hotel harks back to glory days of Chicago in the 1920's- a masterpeice of gleaming marble and vintage fixtures
  Designer Shopping  -  Just down the road you will find the Magnificent Mile of Michigan Avenue, famed for its designer shopping
  Hotel Entertainment  -  20 East the hotel's restaurant is somewhat of a local hotspot and tends to become lively on the weekends
  Sights nearby  -  The renowned House of Blues music venue is less than a mile away and well worth a visit
  Recommended by  -  Tablet
  
  A glamorous great Gatsby style hotel, in a beautifully refurbished 1920's building in downtown Chicago. The comfortable and spacious rooms have been carefully crafted by local designers. The popular on site restaurant draws crowds, as do the cocktails at the vintage bar. An elegant spot. See More
  
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- Freehand, Chicago Chicago (Near North Side) 217 rooms from £66
  
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  Value chic  -  With doubles from as little as $85 per night (or only $25 per person if you're prepared to share a dorm) it's unbeatable value
  Restaurant  -  Cafe Integral offers up Nicaraguan coffee to complement its selection of light breakfast- and cafe-style fare.
  Great walks  -  Every Saturday morning, the hotel arranges for pay-what-you-like walking tours.
  Kayaking  -  Explore Chicago from an unusual angle on a kayaking water tour.
  Recommended by  -  Tablet
  
  Trendy hostel and hotel offering chic but affordable accommodations in exciting downtown Chicago. Popular and busy bar serves craft cocktails and light meals. Rooms are hip with a boutique appeal, high-quality furniture in dark woods, walls decorated with crafts and an effortlessly cool vibe. See More
  
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- Loews Chicago Chicago 400 rooms from £118
  
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  Families  -  As well as helpful equipment, the hotel also provides iPads loaded with age-appropriate games, consoles, toys & activity books
  Value chic  -  Entry-level rates are incredibly reasonable given the central downtown location and five-star facilities
  Sights nearby  -  The city's Wrigley Building, Arts Club of Chicago, Chicago Tribune Tower and Time Life Building are within 500 metres
  Views  -  Floor to ceiling windows allow superb city skyline views; for something special book a lake view suite
  
  Cool, contemporary city style near Chicago's river and lake front. Spacious and grown-up rooms blend a luxury palette of charcoal and silver hues, with enormous windows. Take in lake views from the rooftop bar after a great steak at the restaurant. There's a large pool and welcoming lobby lounge. See More
  
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- Moxy Chicago Downtown Chicago 156 rooms from £94
  
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  Local exploring  -  A great base from which to explore the city, with fun amenities and a cool vibe
  Sights nearby  -  Close to 'Magnificent Mile', many of the city's archictectural icons are nearby such as the Tribune Tower and Wrigley Building
  Views  -  Corner City View rooms offer great city skyline views from floor to ceiling windows
  Great walks  -  It's easy access to the city's River Walk
  
  Buzzing and fun boutique-style hotel. The reception doubles as a bar; expect cocktails on arrival. Decor is contemporary industrial-cool, with splashes of hot pink. Rooms aren't huge but have everything you need. The 24-hour taco restaurant is useful after nightly DJ sets. Perfect for party animals. See More
  
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- The Blackstone Chicago 335 rooms from £146
  
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  City Style  -  A Chicago institution dripping in history which feels cool, chic and on the pulse
  Great walks  -  Grant Park is literally on the doorstep. Explore Millenium Park, world-famous Cloud Atlas and Buckingham Fountain
  Views  -  Many rooms have views of Lake Michigan and Grant Park
  Restaurant  -  Recommended.
  
  Historic grand-dame updated for the 21st-century. Built in the Beaux-Art era, this city-centre luxury hotel is the epitome of boutique glamour. Wood-panelling, chandeliers & double-height ceilings combine with buzzing restaurants, extensive art collection & quirky modern furniture to great effect. See More
  
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- Chicago Athletic Association Chicago (Illinois) 241 rooms from £148
  
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  Sights nearby  -  Millennium Park is in close proximity to the hotel.
  Views  -  Great views from hotel
  Restaurant  -  Recommended.
  Full of character
  
  Gentleman's club in the early 1800s now opens its Venetian Gothic doors to business travellers, leisure seekers and city slickers. Large, retro rooms boasting Millennium Park views. Cherry Circle Room catches the essence of its former dining purpose. Remember the bar up on Cindy's Roof Top Terrace. See More
  
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- The Gwen Chicago 311 rooms from £119
  
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  City Style  -  Will suit those after a brilliant location, understated luxury, beautiful interiors and excellent dining experiences
  Sights nearby  -  Chicago is an architectural heaven. In the area look out for the Wrigley Building, neo-Gothic Tribune Tower & Time Life Building
  Great walks  -  The property is just 2 blocks from the Chicago River; easily get onto the city's scenic River Walk
  Views  -  All the suites come with spectacular city views
  
  Divine transformation from a historic building to a luxury boutique hotel. 1920s sculptor Gwen Lux is behind the façade; Art Deco glamour reigns supreme in the rooms, restaurants & a wrap-around rooftop bar. Expect jewel tones, gold fittings, glossy marble & epic city views. A sexy & stylish stay. See More
  
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- The Kimpton Gray Hotel Chicago 293 rooms from £157
  
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  City Style  -  A suave sophisticated hotel with twin staircases and vintage elevators in the heart of Chicago
  Views  -  Great views from hotel
  Restaurant  -  Recommended.
  Traditional
  Recommended by  -  Tablet
  
  An iconic and elegant building in the Loop's financial corridor. Named for its grey marble exterior, the rooms mirror this toned down grandeur, with the odd splash of colour and quirky design. With a range of bars and restaurants, and excellent 24 hour gym they have all the bases covered. See More
  
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- Hotel Zachary Chicago 173 rooms from £155
  
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  Lively  -  On game days the hotel's public spaces are busy; expect plenty of people and plenty of noise... and a lot of fun
  Short break  -  The only place to stay if you're flying into Chicago for a big game
  Sights nearby  -  The nieghbourhood's big attraction is Wrigley Field, the baseball stadium home to the Chicago Cubs. Make sure to catch a game
  Views  -  Great views from hotel
  
  Lively boutique hotel opposite Wrigley Field baseball stadium. An industrial conversion masterclass, interiors are cool, contemporary and yet cosy; expect a sophisticated grey palette with fun baseball-themed touches & large-scale artworks. Dining spaces are the real draw and popular with locals. See More
  
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- Hotel EMC2 Chicago 195 rooms from £186
  
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  City Style  -  'Where science and art meet' is the hotel's theme; it has resulted in a quirky yet chic, incredibly original Chicago property
  Sights nearby  -  Architectural lovers will appreciate their surroundings; visit Time Life Building, Chicago Tribune Tower and Water Tower Chicago
  Great walks  -  It's just over 1km to the city's most famous park - Millenium Park - known for its Cloud Gate sculpture
  Views  -  Great views from hotel
  
  Funky boutique-style hotel located in Chicago's lakeside neighbourhood. Rooms are contemporary luxury with a twist; think Dali-esque murals, glass showers with copper tubing, dark wood floors & colourful art. The double-height restaurant and bar are buzzing. Fun and comfort in equal measure. See More
  
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- The Publishing House Chicago 13 rooms from £176
  
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  Local markets  -  Check out Randolph Street Market, the West Loop’s monthly vintage bonanza. Its food-focused rival is Chicago French Market
  Hideaway  -  With plenty of books to choose from in the hotel library, curl up in one of the reading nooks
  Restaurant  -  Complimentary breakfast
  Views  -  Stunning city views
  Recommended by  -  Mr & Mrs Smith
  
  A boutique B&B offering hip design in the trendy West Loop. Featuring a heaving library and author-themed rooms with books to match. A home-cooked breakfast feast is provided for each guest and there's a round-the-clock pantry. A charming and central base to explore the city from. See More
  
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- Thompson Chicago Chicago (21 E Bellevue Pl) 247 rooms from £219
  
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  Lively  -  Salone Nico is a favourite of Chicago bussiness types on an evening.
  Sights nearby  -  Buckingham Fountain is a must see, as well as 'The Bean'.
  Great walks  -  Grant Park and Lincoln Park are both worth a visit.
  Views  -  Either of Lake Michigan or the Chicago skyline.
  Recommended by  -  Mr & Mrs Smith, Tablet
  
  Among the Chicago Mansions, this lively and trendy hotel offers prime location for Magnificent Mile and lakeside views. Contemporary rooms with noteworthy comfortable beds and waterfall showers, offering room service as well as Nico Osteria restaurant for fine Italian cuisine and wines. See More
  
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- The Guesthouse Hotel Chicago 25 rooms from £146
  
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  Families  -  You won't need to bring much; helpful equipment like high chairs, pushchairs, cots, bath accessories, games & toys are provided
  Sights nearby  -  It's easy to head into central Chicago on public transport for the day; visit Millenium Park, Magnificent Mile and Museum Campus
  Spa  -  The hotel partners with the day spa next door to provide in-room treatments
  Full of character
  
  Fantastically fully-equipped one, two & three-bedroom self-catered apartments in Chicago's Anderson district. Each of the fresh, lofty and spacious units provides everything expected from a lovely home; dishwashers, driers, gym, balconies & even a roof terrace. A comfortable option for long stays. See More
  
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