Explore the Second City from the best hotels in Chicago
From iconic cuisine and world-famous comedy to waterfront walks and unbeatable shopping, Chicago (and its best hotels) will give you the trip of a lifetime.
By Cassandra Brooklyn | July 24, 2025
Cassandra Brooklyn
Cassandra Brooklyn is a freelance writer and guidebook author specializing in travel, accessibility, sustainability, and all things outdoors. Originally hailing from the Midwest, she now lives in New York City but escapes to adventures around the world as often as possible. She's the author of the cycling guidebook, Cuba By Bike, has contributed to multiple guidebooks about Egypt, Portugal, and the United States, and she has bylines in The New York Times, Wall Street Journal, National Geographic, Forbes, The Daily Beast, and Lonely Planet, among others.
Chicago may officially be known as the Windy City, but there’s way more to this city than occasional gusts. Instead, visitors will be blown away by the city’s vibrant nightlife, world-class museums, stunning waterfront, and fabulous food. Whether you’re seeking a romantic, relaxing vacation focused on art and architecture, or an exciting nightlife-filled getaway with friends, staying at these best hotels in Chicago makes it easy to explore everything the city has to offer.
Canopy by Hilton Chicago Central Loop
With so much to do in Chicago, you’ll get the most out of your trip by basing yourself right in the middle of the action. For modern comfort in the Financial District (aka “The Loop”), look no further than Canopy by Hilton Chicago Central Loop, which is surrounded by the city’s best entertainment and attractions. Here, classic meets contemporary, and you’re mere minutes from top sites like Millennium Park, the Art Institute of Chicago, Willis Tower Skydeck, and the Chicago Riverwalk. Consider borrowing one of the hotel’s complimentary Canopy Bikes to explore on two wheels and pedal up to the zoo, over to Wrigley Field for a ballgame, or to one of numerous Lake Michigan beaches for some fun in the sun. Come dinnertime, head back to the hotel's rustically refined Seville Chicago restaurant, where Mediterranean-inspired seafood dishes, tapas, and a separate vegan menu are paired with craft cocktails and an extensive international wine list.
theWit Chicago, a Hilton Hotel
Don’t let the classic architecture fool you — Chicago is a modern city that boasts cutting-edge technology across all forms of entertainment. Think world-class museums, sporting events, and concert venues. Hotels have also stepped up in this area, and theWit Chicago, a Hilton Hotel is the perfect example. A Four Diamond, multi-sensory hotel, visit its award-winning ROOF on theWit bar and nightclub to experience how technology meets elegance alongside delicious food, renowned DJs, and high-energy dancing. Some of the city’s top attractions are just blocks away, like the Chicago Theater and Navy Pier, where you’ll find no shortage of cultural attractions. For dinner, head back to the hotel’s elegant State and Lake Chicago Tavern, which blends a neighborhood pub vibe with refined bistro cuisine (think Faroe Island salmon and prime T-bone steaks). The tavern also offers an excellent BBQ Blues Brunch every Saturday and Sunday, where you can savor authentic barbecue, cornbread, and old-fashioned drinks with a side of live blues music.
Waldorf Astoria Chicago
Chicago is famous for its shopping, and there is nowhere better to browse than Magnificent Mile (Michigan Ave). Explore luxury shops like Balenciaga, Bottega Veneta, and Tiffany & Co., along with the famed American Girl Chicago — an irresistible stop for little ones. Just one block off Magnificent Mile is the not-to-be-missed Museum of Contemporary Art, which hosts some of the country’s most ambitious modern art exhibitions. For close proximity to the best shopping, art, and museums in Chicago, book a room at Waldorf Astoria Chicago. In this downtown Gold Coast hotel, 1920s Parisian charm meets modern European elegance. Rooms come with high ceilings, fireplaces, and large terraces, while 24-hour butler service ensures easy access to anything your heart desires. If you’re looking for ways to occupy your downtime, treat yourself to an appointment at the hotel’s award-winning Spa or indulge in an elegant dinner at Brass Tack before heading up to the intimate second-floor lounge to unwind with classic cocktails at Bernard’s.
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