
Hotels in Chicago
Find and book unique hotels on Airbnb
Quick stats about hotels in Chicago

Total holiday rentals
Explore 550 holiday rentals in Chicago

Nightly prices starting at
Chicago holiday rentals start at $52 SGD per night before taxes and fees

Verified guest reviews
Over 15,770 verified reviews to help you choose

Family-friendly holiday rentals
100 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 220 rentals that welcome pets

Holiday rentals with a pool
110 properties feature pools

Rentals with dedicated workspaces
460 properties have a dedicated workspace

Wifi availability
550 of Chicago holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chicago rentals

Nearby attractions
Chicago’s top spots include Millennium Park, Wrigley Field and Lincoln Park
Top-rated hotels in Chicago
Guests agree: these hotels are highly rated for location, cleanliness and more.

Warwick Allerton Hotel Chicago
The beautifully rejuvenated Warwick Allerton - Chicago offers charming accommodations at a storied Michigan Avenue address. Experience boutique ambience in one of The Windy City’s grandest hotels. From its inception in the early 1920’s, this timeless classic has been the standard bearer of Jazz Age style and sophistication and remains a noteworthy landmark in the Chicago skyline. Our stylishly designed rooms, renowned Warwick hospitality, and convenient location make it perfect for your stay.

Modern design with VU Skyward rooftop bar
Refundable Incidental hold of $75/day required at check in. Must be 21+ to book/stay. We are connected to McCormick Place Convention Center and Wintrust Arena via sky-bridge. The nearby subway train brings guests to Millennium Park and downtown attractions. Soldier Field and the Museum Campus are within a mile are within a mile. Guests can enjoy a view of Chicago and Lake Michigan at our VU Skyward rooftop bar. We also have a Starbucks in our lobby. Self Parking is available for $52/night.

The Swissôtel Chicago
$35.22 Resort Fee to be collected on property Swissotel Chicago is an award-winning luxury hotel overlooking the Chicago River and Lake Michigan, and just steps from the Magnificent Mile. The distinctive 4-diamond, all-glass hotel offers spectacular wrap-around views from Navy Pier to Millennium Park and has a state-of-the-art penthouse fitness center. The room may not look the same as the room in the photo as this room is run of house and selected by the hotel at check in.

Near O’Hare Airport + Breakfast. Shuttle. Pool.
Steps from the Allstate Arena and minutes from O'Hare International Airport, Staybridge Suites Chicago O'Hare offers the perfect extended-stay experience in Rosemont. Relax in spacious suites featuring full kitchens and living areas. Enjoy a complimentary hot breakfast daily and evening socials on select nights. Amenities include a heated indoor pool, fitness center, and free airport shuttle. Close to the Fashion Outlets of Chicago and the Blue Line for easy city access.

Suite 509 | Stay One Chicago
Stay One Chicago is a refined boutique hotel offering elevated comfort in the heart of the city. Guests enjoy beautifully designed rooms with high-end finishes, seamless self check-in, and dedicated workspace. Indulge in three on-site restaurants featuring curated dining options, perfect for breakfast, dinner, or cocktails. Your stay also includes exclusive access to Lifetime for premium fitness and wellness amenities, creating a complete luxury lifestyle experience.

2 Queen Bed Room in Theatre Dst
Experience upscale accommodations and amenities in the heart of Chicago when you stay at Cambria Chicago Loop - Theatre District. Our hotel, located conveniently close to some of Chicago's top attractions, is ideal for both business travel and vacations. Make the most of your stay with our top-notch services and on-site restaurant that offers classic American cuisine. Unwind and relax in our comfortable guest rooms with Chicago-inspired décor.

Close to Lewis University + Free Breakfast
Unwind in your own spacious suite just off I-55—perfect for road trippers, weekend shoppers, or anyone craving space to breathe. Grab free breakfast, chill in the indoor pool, or explore nearby favorites like IKEA and The Promenade. Whether you’re headed to Naperville, downtown Chicago, or just hanging in Bolingbrook, this stay gives you all the space and perks you need—without giving up comfort, convenience, or that extra travel magic.

Arlo Chicago
Step into the city king room where inspiring views of downtown and a spacious cozy king bed invite you to relax in style. Enjoy smart amenities like a Nespresso coffee machine, a 55 inch flat screen TV, a smart fridge and a work desk. Contemporary luxury design and thoughtful details like a hand held steamer hair dryer and laptop sized safe make this a perfect home base whether you are exploring the city or enjoying a quiet night in.

The Robey Hotel Urban King Room
Experience the vibrant heart of Chicago at The Robey, where historic architecture meets modern design in the bustling Wicker Park and Bucktown neighborhoods. With 89 elegantly appointed rooms and a variety of dining options including Cafe Robey for all-day brunch and The Up Room for rooftop cocktails with panoramic city views, The Robey offers a unique blend of comfort, style, and culinary delights for every traveler.

Close to Navy Pier + Restaurant. Bar. Gym.
Tucked just off the Magnificent Mile, Hotel Saint Clair gives you front-row access to Chicago’s must-sees—think Navy Pier, Millennium Park, and late-night eats around the corner. Sip your morning coffee, grab your camera, and hit the lakefront in minutes. The rooms are pet-friendly, WiFi’s on the house, and everything you want to see is walkable. It’s your laid-back launchpad for big city adventures.

Near O’Hare Airport + Pool. Dining.
Unwind at The Westin Chicago Northwest, a lakeside getaway with spacious rooms, indoor pool vibes, and Insta-worthy sunsets just outside the city. Wake up with Starbucks coffee on-site, sweat it out in the 24/7 gym, then explore nearby Schaumburg shops, Busse Woods trails, and hidden local dining gems. Perfect for a weekend adventure, a friends’ trip, or recharging between flights.

Level Chicago - Fulton Market
Studio suites feature a king bed and a sofa bed with a comfortable living area and complimentary wifi. Includes a full kitchen with a kitchen area and in suite laundry. Offers a spa inspired bathroom with malin goetz amenities, air conditioning and smart TV. Non smoking and pet friendly suite with access to outdoor pool, hot tub, fitness center and cloud lounge.
Popular amenities for Chicago hotels
Family-friendly hotels

Riu Plaza Chicago

The Royal Sonesta Chicago Downtown

Private Quad in Downtown + On Site Dining

Lincoln Park gem with storied jazz & rock history

The GEM Museum Suites - Evanston

The Emily Hotel

Millennium Knickerbocker Hotel Chicago

Majestic Hotel
Hotels with a pool

Viceroy Chicago

Comfort and Relaxation! Parking, Near Navy Pier

Eaglewood Resort & Spa Chicago

Hotel - Jet Tub, King Bed, Bfast Included

Close to Oakbrook Center + On-site Dining & Pool

LEVEL Chicago - Old Town

Stay Downtown | Rooftop pool. Gym

Perfect Destination! Onsite Bar and Restaurant!
Other hotel holiday rentals

The Champagne Lodge & Luxury Suites - Adults Only

Rare upscale Gold Coast boutique find

Chicago Hotel Collection Ambassador Gold Coast

Relaxing Stay Downtown! Pets are Allowed

The Godfrey Hotel Chicago

The Allegro Royal Sonesta Hotel Chicago Loop

River North Gem! Minutes to Magnificent Mile.

Stylish Room with Rooftop Lounge & City Views
Destinations to explore
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- Wrigley Field
- Soldier Field
- Lincoln Park
- United Center
- Grant Park
- Navy Pier
- Millennium Park
- Indiana Dunes State Park
- Naval Station Great Lakes
- 875 North Michigan Avenue
- Six Flags Great America
- The Field Museum
- Shedd Aquarium
- Chicago River Walk
- Humboldt Park
- University of Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Loyola University Chicago
- Donald E Stephens Convention Center
- Union Park
- Frank Lloyd Wright Home and Studio
- Washington Park Zoo
- Garfield Park Conservatory
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