The Best Chicago Hotels To Book
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The Best Chicago Hotels To Book

Picture of Stephanie Chang Avila
Updated: 22 May 2019
Chicago blends Midwest charm with the swank and glamour of America’s great coastal cities to forge a design culture of its own. From the opulent grandeur of the venerable Drake Hotel to the resolutely contemporary food-meets-travel ethos of Longman & Eagle, we discover the best hotels of Chicago.

The Drake

The Drake exudes opulence, from its classic Italian Renaissance-inspired décor to its chandeliered lobby. This historic hotel, which first opened its doors in the heady days of the Roaring Twenties, has become a Chicago icon, playing host to a who’s-who of the world including Bing Crosby, Walt Disney, Joe DiMaggio and Marilyn Monroe, as well as numerous heads of states. One of Chicago’s top historic luxury hotels, The Drake offers guests a stylish stay evoking old world charm. Afternoon tea is a must-try, and Chicago’s rich cultural offerings are just a short walk from the hotel.

Address: The Drake Hotel, 140 E Walton Pl, Chicago, IL 60611 

The James

Truly an arts hotel, The James features its own art galleries that hold exhibitions regularly throughout the year, featuring works from local and international artists. In addition, The James is a mere block away from the Magnificent Mile, where visitors can explore Chicago’s vibrant museums, including the renowned Art Institute of Chicago, walk down to the Navy Pier, stroll around Millennium Park and visit the city’s many excellent restaurants and eateries. And, if you’re travelling further afield, The James offers a complimentary car service. For those craving a hefty bite, David Burke’s Primehouse wins rave reviews from Chicagoans and visitors alike for being the best steakhouse in town.

Address: The James Chicago, 55 E Ontario St, Chicago, IL 60611

Longman & Eagle

A trendy design hotel sitting atop a Michelin-starred restaurant and a whisky bar serving over 150 different whiskies, Longman & Eagle is a foodie traveller’s dream come true. Longman & Eagle offers ‘a modern take on an old Chicago neighborhood inn’ and is one of the top destinations for a truly boutique stay in Chicago. Simplicity governs the design aesthetics, and each room features unique décor with a different ambiance. The hotel is a great launch pad for exploring the city, as well as relaxing and unwinding with an Apple TV, a media player, and designer furniture by Robert McAdams and Jon Martin, as well as vintage decorative touches and original artwork. What’s more, the food downstairs is amazing, and one can hardly be faulted for never stepping outside of the hotel’s Logan Square locale. Diners rave about the burger, the bone marrow, the whisky and just about everything else on the menu.

Address: Longman & Eagle, 2657 N Kedzie Ave, Chicago, IL 60647

Hotel Lincoln

Hotel Lincoln in the Lincoln Park neighborhood of Chicago Each room features original artwork and cool-vintage design details; taking full advantage of its excellent location, rooms on floors 9-12 overlook Chicago’s famous Lincoln Park or offer a scenic panoramic view of Lake Michigan. A short drive from Chicago’s most famous landmarks such as the Navy Pier, the Loop and the Magnificent Mile along N Michigan Avenue, visitors can also take a lovely stroll through Lincoln Park and walk along the Lakefront Trail to soak up Chicago’s waterfront view.

Address: Hotel Lincoln, 1816 N Clark St, Chicago, IL 60614

Villa D’Citta

Villa D’Citta is a charming boutique bed & breakfast housed in an Italianate mansion in the heart of the Lincoln Park neighbourhood of Chicago. A short drive from downtown Chicago, Villa D’Citta is a great place from which to explore the city without the frenetic big-city feel of Chicago’s busy downtown. This calm oasis in the midst of the sprawling city features its own grotto with a barbeque grill, spacious rooms, beautiful four-poster beds, a rooftop terrace and a jacuzzi.

Address: Villa D’Citta Bed & Breakfast, 2230 N Halsted St, Chicago, IL 60614


PUBLIC Chicago

Vintage meets avant-garde at the PUBLIC hotel, which transformed the legendary Ambassador East into a destination for the design-conscious, contemporary traveller without losing any of its historic, understated glamour. Along with the Ambassador East, the PUBLIC inherited the fabled Pump Room restaurant, once frequented by the likes of Marilyn Monroe, Frank Sinatra and Humphrey Bogart. The Pump Room is essentially a new restaurant under the old name, and is headed up by James Beard award winner Jean-Georges Vongerichten. Serving organic farm-to-table fare, the food is simple, delicious, healthy and affordable; Chicagoans have taken notice, and Pump Room’s new American food concept has launched the restaurant into the upper echelons of foodie destinations in the city.

Address: PUBLIC Chicago, 1301 N State Pkwy, Chicago, IL 60610

Hotel Sax Chicago

Located adjacent to Chicago’s iconic House of Blues, Hotel Sax Chicago’s eclectic Art Deco-inspired décor and undeniably central location near The Loop, the Navy Pier and Millennium Park makes this hotel a favourite amongst the urban-chic crowd. In addition, Hotel Sax’s Crimson Lounge wins rave reviews for its swanky Victorian-vintage style and great ambiance.

Address: Hotel Sax Chicago, 333 N Dearborn St, Chicago, IL 60654