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

Total vacation rentals
Explore 550 vacation rentals in Chicago

Nightly prices starting at
Chicago vacation rentals start at $55 CAD per night before taxes and fees

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

Family-friendly vacation rentals
100 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 220 rentals that welcome pets

Vacation rentals with a pool
110 properties feature pools

Rentals with dedicated workspaces
460 properties have a dedicated workspace

Wifi availability
550 of Chicago vacation 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.

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. Valet Parking is available for $62/night.

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.

Near Downtown Bolingbrook + 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.

City king
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.

Executive one bedroom suite
Executive one bedroom suite offers a bright, modern retreat with separate living area, ideal for extended stays and relaxed city breaks. Enjoy comfortable living area, sofa bed, fully equipped kitchen, coffee and tea maker, designated workspace, walk in closet, air conditioning, bathroom amenities, bathrobe, smart TV, complimentary wifi, local calling, iron and board, pet friendly setting, and non smoking.

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 room
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.

Standard king
Standard room offers a tastefully decorated space with a plush king bed designed for your comfort and relaxation. Enjoy modern amenities like WiFi, smart TV and an in room safe along with coffee and tea making facilities. Thoughtful touches create a welcoming atmosphere for both work and leisure making it an ideal choice for any traveller. Unwind and recharge in style during your stay.

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.
Popular amenities for Chicago hotels
Family-friendly hotels

One queen bed non smoking

Near Wheaton College | Bistro Bar & Pet-friendly

King suite

Standard king

Sports Illustrated Resorts Chicago Studio King

A Relaxing Stay In Cook County Near O'Hare | Pool

Club Quarters Hotel Central Loop, Chicago, Club...

Deluxe family king room
Hotels with a pool

Near Drury Lane Theatre + Dining, Pool & Gym

Better Choice for your Vacation! Indoor Pool!

Close to Chicago O'Hare Airport + Free Breakfast

Executive one bedroom suite

Golf view two queen beds room

Two king corner suite

Comfort and Relaxation! Parking, Near Navy Pier

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

Lincoln Park gem with storied jazz & rock history

Deluxe two queens - city view

Standard Room with King Bed

Near Medinah Country Club + Breakfast & Kitchen

1 King Bed | La Quinta O'Hare | Breakfast Included

The Chicago Hotel, Upscale Deluxe Double Queen

Deluxe - queen

Standard queen
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- Wrigley Field
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