Where to Book a Stay in Chicago, Illinois

Book a room with a view on your next trip to Chicago
Book a room with a view on your next trip to Chicago | © Brad Knight / Unsplash
Photo of Amy Blyth
18 November 2020

The Windy City is a magnet for culture seekers, home to some of the country’s most captivating museums, parks, and art galleries. It’s also full of top hotels, many set near the Magnificent Mile in soaring skyscrapers or historic buildings that date back to the 1920s. Here are the best places to stay in Chicago, bookable with Culture Trip.

The Robey

Boutique Hotel
A compact, art-deco-inspired guestroom at the Robey with a double bed, dark-wood floor and two black-frame windows
Courtesy of The Robey / Hotels.com
This hipster hotel lies in the trendy Wicker Park neighborhood, in a former 1900s warehouse and tower. Choose from annex lofts or tower rooms, with various mid-century furniture, vintage phones, art-deco bronze lifts, and lofty ceilings. Highlights include the rooftop bar and pool with views of the Chicago skyline, free guest bikes, and a fashionable lobby with huge windows. Don’t miss the ground-floor Cafe Robey, which serves American hot dogs.

The Peninsula

Potted palm-trees line an indoor swimming pool at the Peninsula Chicago, while large windows offer views over the city
Courtesy of The Peninsula Chicago / Expedia
At the Peninsula, exceptional Asian-style service comes as standard. The five-star hotel near Michigan Avenue is popular with celebrities and exudes elegance. Picture marble floors, framed art, and picture windows with supreme skyline views. The opulent spa is perfect for a pamper session or you can work out in the fitness center and half Olympic-sized pool. Have high tea at the Lobby restaurant or dim sum at the Shanghai Terrace. In winter, you can even ice-skate on the rooftop.

Radisson Blu Aqua Hotel

The striking Radisson Blu Aqua Hotel is a skyscraper with concrete waves around the outside
Courtesy of Radisson Blu / Expedia
Radisson Blu’s signature wave-themed exterior stands out among downtown Chicago’s skyscrapers, set across from Millennium Park. Inside, the decor is contemporary-chic, with a fireplace lobby, Chicago-themed art, and a continuing wave design, which leads to rounded balconies with city views. Enjoy large pools and a spa, a running track on the third-floor terrace, and a gym with a basketball court.

The Langham

Cream-toned room at The Langham with a four poster bed and floor-to-ceiling windows
Courtesy of the Langham / Expedia
Stay at the Langham for unparalleled views over the river and Lake Michigan, plus a Bauhaus design scheme. Put together by architect Ludwig Mies van der Rohe, the hotel bears his signature 1970s steel and glass design, decorated with extensive art, warm tones, and dark woods. Book the cinema suite for a movie, take a dip in the pool, or visit the award-winning Chuan Spa. There’s also American dining at the Travelle Kitchen and Bar.

Four Seasons Hotel Chicago

A modern bar with lots of bottles at the Four Seasons Chicago
Courtesy of Four Seasons / Expedia
Chicago’s Four Seasons lives up to its brand reputation, with modern luxury characterized by plush carpets, cutting-edge amenities, and large windows. The hotel occupies an impressive plot near the Magnificent Mile and lake-or-city-view rooms provide coffee machines and Netflix. There’s also a house car that offers 2mi (3.2km) radius trips, a 50ft (15m) pool, fitness center and lobby bar with urban views. Be sure to schedule a visit to the spa, whirlpool and steam room.

The Hoxton

The rooftop pool at the Hoxton, with guests swimming and the Chicago skyline as a backdrop
Courtesy of The Hoxton / Expedia
Set in the heart of the lively Fulton Market district, The Hoxton has 182 mid-century-style rooms with floor-to-ceiling windows that showcase skyline views. Expect a warehouse feel, with concrete ceilings and paneled leather headboards, as well as bedding from Chicago local Cody Hudson. “The Working From” co-working space buzzes with activity, as does the Peruvian rooftop restaurant Cabra Cevicheria and Lazy Bird Cocktail Bar, which has live music on the weekends.

Conrad Chicago

The rooftop terrace with cream-toned seating, fairy lights and city views at the Conrad Chicago
Courtesy of Conrad Chicago / Expedia
Come to Conrad Chicago for a glamorous stay on a peaceful street just off Michigan Avenue. Previously an office, the 20-story building retains its glassy exterior but has been redesigned by French firm Pierre-Yves Rochon with a statement staircase, lobby with bone China sculpture, and elegant furnishings. Rooms and suites come in earthy tones with awe-inspiring city views and black granite bathrooms. Head to Baptiste & Bottle for a bourbon tasting session.

Eaglewood Resort and Spa

Aerial shot of Eaglewood Resort and the surrounding golf course
Courtesy of Eaglewood Resort / Expedia
The four-star Eaglewood Resort and Spa lies in Itasca, just north of Chicago’s central hub. Golf fans come to try out the 18-hole championship, par 72 course, set among lakes and trees. Treat yourself to a pamper session at the spa with a sauna and outdoor pool deck. There’s also a bowling alley and restaurant. Rooms and suites are decked out in cherry and mahogany wood with balconies and patios to show off golf course views.

The Hotel at Midtown

Five-lane outdoor pool with black sun loungers at The Hotel at Midtown
Courtesy of the Hotel at Midtown / Expedia
Calling all fitness fanatics: the Hotel at Midtown is a world-leading health resort with facilities spread over three levels. Check out the multiple pools, boxing ring, fitness studios, and gyms, as well as 16 tennis courts. Originally built as the world’s largest tennis club, there’s even a suite created by Venus Williams’ design firm. Rooms have a clean, minimalist design with graffiti art and skyscraper views. Guests can dine at the healthy Chromium farm-to-table restaurant.

Hotel Zachary

The brick-and-glass Hotel Zachary is separated from Wrigley Stadium by a four-lane road and pedestrianized space outside the arena
Courtesy of Hotel Zachary / Expedia
Hotel Zachary is the place to stay if you’ve come to watch the Chicago Cubs play baseball. The boutique hotel is just steps from Wrigley Field and its premium rooms even offer tantalizing glimpses of the action. On game days, the hotel’s bars and restaurants are filled with excitable fans. Hotel Zachary is named for the Chicago architect who designed Wrigley Field, Zachary Taylor Davis and is filled with baseball memorabilia, exposed pipes, and brick walls.

Lincolnshire Marriott Resort

Modern, cream-toned room at the Lincolnshire Marriott Resort with a double bed, a couch, a TV and a writing desk
Courtesy of Lincolnshire Marriott Resort / Expedia
Just north of Chicago’s center, the Lincolnshire is a fancy golf and spa resort brought to you by the Marriott. Following a $28m renovation, the 175-acre (70ha) resort is modern and sleek, with a spa, five restaurants, and three outdoor pavilions. The main draw is the 18-hole PGA Championship golf course but there’s also a pool, tennis courts, and award-winning live musical theatre at the in-house Marriott Theatre.

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