
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 £30 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.

King Room in Downtown
Experience upscale accommodations &amenities in the heart of Chicago when you stay with us. 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 & on-site restaurant that offers classic American cuisine. Unwind & relax in our comfortable guest rooms with Chicago-inspired décor. Whether you are traveling alone or with family, our hotel will give you a once in a lifetime experience.

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.

Millennium Knickerbocker Hotel Chicago
Accessible standard king bath offers comfort and convenience with premium bedding blackout drapes and a pillowtop mattress ensuring restful nights. The private bathroom features designer toiletries bathrobes and a shower while closed captioned TV and free WiFi keep you connected. Unique touches include eco friendly cleaning supplies, a coffee and tea maker and connecting rooms available for added flexibility. Relax and enjoy thoughtful amenities designed for a pleasant stay.

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.

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.

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.

Central Loop Hotel
Classic rooms are ideal for solo travelers or couples seeking comfort and value in Chicago. Each room features a queen size bed with premium bedding, a versatile workspace with ergonomic chair, and lightning-fast free Wi-Fi. Enjoy a flat-screen smart TV, Nespresso coffeemaker, and bathroom amenities by C.O. Bigelow. Yoga mats and resistance bands are available upon request for added convenience.

Lincoln Park gem with storied jazz & rock history
Start your Chicago adventure at Hotel Versey—a boutique gem blending European flair with local charm in the vibrant Lincoln Park/Lake View neighborhood, just three miles from downtown. Steps from DePaul University and close to top spots like the Magnificent Mile, Navy Pier, and Museum Campus, Hotel Versey offers stylish comfort and unbeatable convenience for both business and leisure travelers.

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.

Riu Plaza Chicago
Deluxe two queen bedrooms are spacious and cozy rooms are ideal for your stay in vibrant Chicago. Enjoy modern comforts like a shower, hairdryer, central heating, and air conditioning. Additional amenities include an in-room safe, small fridge, coffee maker, and iron. Settle in and relax, everything you need for a comfortable visit awaits.
Popular amenities for Chicago hotels
Family-friendly hotels

The Royal Sonesta Chicago Downtown

The GEM Museum Suites - Evanston

The Emily Hotel

Minutes from Downtown | Free Breakfast & Parking

Near Medinah Country Club + Breakfast & Kitchen

Majestic Hotel

Peaceful Retreat In Cook County | Restaurant

Close to O’Hare Airport | Bar. Gym + Pet-Friendly
Hotels with a pool

Level Chicago - Fulton Market

Viceroy Chicago

Eaglewood Resort & Spa Chicago

Hotel - Jet Tub, King Bed, Bfast Included

LEVEL Chicago - Old Town

Perfect Destination! Onsite Bar and Restaurant!

Close to Oakbrook Center + On-site Dining & Pool

Better Choice for your Vacation! Indoor Pool!
Other hotel holiday rentals

Club Quarters Hotel Wacker at Michigan, Chicago

The Godfrey Hotel Chicago

The Allegro Royal Sonesta Hotel Chicago Loop

River North Gem! Minutes to Magnificent Mile.

Staypineapple, An Iconic Hotel, The Loop

Private Quad in Downtown + On Site Dining

Stylish Room with Rooftop Lounge & City Views

The Royal Sonesta Chicago River North
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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
- Chicago River Walk
- The Field Museum
- Shedd Aquarium
- University of Chicago
- Humboldt Park
- Guaranteed Rate Field
- Lincoln Park Zoo
- Loyola University Chicago
- Union Park
- Frank Lloyd Wright Home and Studio
- Donald E Stephens Convention Center
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- Washington Park Zoo
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