Cool Hotels in Chicago | The Hotel Guru

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.

17 Cool Hotels in Chicago

Thompson Chicago

Chicago (Near North Side)

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.

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.

from AU$431 for 1 room, 1 night including taxes & fees

17 Cool Hotels in Chicago

For a rooftop pool

For the design

For a glamorous stay

For families

For a lively stay

For city style

For a boutique

For luxury

For an apartment

Still not sure where to book?

17 Cool Hotels in Chicago

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