Curator’s statement
We love to do big things in Chicago. The birthplace of the skyscraper and a hub of innovation, Chicago is a city where big and bold ideas come to life. Our legacy of hosting unforgettable events dates all the way back to the World's Columbian Exposition of 1893. From world-class music festivals like Lollapalooza to iconic sporting events such as the Chicago Marathon and the annual St. Patrick's Day Celebration, the Windy City pulls out all the stops. Whether you're here for music, sports, festivals, business or shopping, staying downtown puts you in the heart of the action. Luckily, you don’t have to spend a fortune to enjoy it all. Here’s your locally-curated complete guide to stylish yet affordable hotels, each under $300 per night, so you can experience Chicago’s best without breaking the bank.
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Where to stay in Chicago
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Things to do in Chicago
Chicago Athletic Association Hotel
Vibe: Historic grandeur with modern luxury
Why stay here: Once an elite private club, this iconic hotel combines timeless architecture with upscale amenities. The on-site bars and restaurants, like Cindy’s Rooftop, are a must-visit for incredible lake views.
Nearby attractions: Millennium Park, Art Institute of Chicago, Grant Park
Pro tip: The prime location makes this hotel perfect for both Lollapalooza and the Chicago Marathon, with easy access and views of Grant Park.
Thompson Chicago
Vibe: Sophisticated and understated luxury
Why stay here: Located in the upscale Gold Coast neighborhood, Thompson Chicago offers a polished stay with spacious rooms, premium linens and a chic on-site restaurant, Nico Osteria.
Nearby attractions: Oak Street Beach, Magnificent Mile, Historic Gold Coast mansions
Kimpton Gray Hotel
Vibe: Modern elegance in a historic setting
Why stay here: Situated in the Loop, this boutique hotel offers a sophisticated stay with plush furnishings, a rooftop bar and free yoga mats in every room. Its central location makes it a convenient base for exploring Chicago’s main attractions.
Nearby attractions: Willis Tower, Chicago Riverwalk, The Loop’s Theater District
Pro tip: Great for Chicago Marathon runners and spectators thanks to its proximity to public transportation, the starting line and key race points.
The Pendry Chicago
Vibe: Contemporary luxury with a bold edge
Why stay here: Located in the historic Carbide & Carbon building, The Pendry combines Art Deco glamor with modern flair. Guests rave about the rooftop bar and proximity to top attractions.
Nearby attractions: Millennium Park, Chicago Riverwalk, Magnificent Mile
Pro tip: Great for St. Patrick’s Day because it’s near the Chicago River dyeing ceremony and festivities.
The Fairmont Chicago
Vibe: Refined and elegant with scenic park and lake views
Why stay here: Situated steps from Millennium Park, The Fairmont blends modern sophistication with thoughtful service. Guests love the spacious rooms and location, location, location.
Nearby attractions: Millennium Park, Navy Pier, Art Institute of Chicago
JW Marriott Chicago
Vibe: Sophisticated luxury with top-tier amenities
Why stay here: For those seeking luxury on a budget, the JW Marriott in the Loop delivers with spacious rooms, a world-class spa and impeccable service. It’s an excellent choice for both business and leisure travelers.
Nearby attractions: Union Station & Ogilvie Station, Willis Tower, Art Institute of Chicago
The Talbott Hotel
Vibe: Classic charm with boutique hospitality
Why stay here: Nestled on the Gold Coast, The Talbott is perfect for travelers seeking a quieter, upscale stay. The hotel is a great choice for families or solo travelers.
Nearby attractions: Oak Street Beach, Magnificent Mile, Museum of Contemporary Art
Sofitel Chicago
Vibe: Sleek French elegance in the heart of the city
Why stay here: Designed by architect Jean-Paul Viguier, the Sofitel’s striking modern design complements its luxurious accommodations. The hotel is renowned for its French-inspired cuisine, artistic sensibility and attentive service.
Nearby attractions: Water Tower Place, John Hancock Center, Museum of Contemporary Art
Omni Chicago
Vibe: Spacious suites with a touch of elegance
Why stay here: Located right on the Magnificent Mile, Omni Chicago offers all-suite accommodations, perfect for families or travelers who appreciate extra space. The rooftop sundeck and indoor pool are standout features for relaxing after a day of exploring.
Nearby attractions: Magnificent Mile shopping, John Hancock Center, Oak Street Beach
The Westin Michigan Avenue
Vibe: Relaxed luxury with stunning river views
Why stay here: Overlooking the Chicago River, The Westin offers spacious rooms, signature Heavenly Beds® and a serene vibe perfect for unwinding after exploring the city. The fitness center and on-site dining options make it a well-rounded choice for any traveler.
Nearby attractions: Chicago Riverwalk, Millennium Park, Magnificent Mile
Need to know
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Jonna Robertson
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For more inspiration and insider recommendations, visit our Chicago page.