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

Total holiday rentals
Explore 450 holiday rentals in Chicago

Nightly prices starting at
Chicago holiday rentals start at $28 AUD per night before taxes and fees

Verified guest reviews
Over 11,810 verified reviews to help you choose

Family-friendly holiday rentals
90 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 210 rentals that welcome pets

Holiday rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
390 properties have a dedicated workspace

Wi-Fi availability
450 of Chicago holiday rentals include Wi-Fi 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. Self Parking is available for $52/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.

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.

Riu Plaza Chicago
The deluxe family king room is a perfect choice for families visiting Chicago, offering plenty of space and comfort for your city getaway. Enjoy amenities like central heating, air conditioning, and an in-room safe to ensure a relaxing stay. A small fridge, coffee maker, and sofa bed add extra convenience for your family. Practical touches such as a shower, hairdryer, and iron are also included for your comfort.

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.

Elegance and comfort in Gold Coast neighborhood
Less than a mile from Oak Street Beach and the lakefront, our hotel offers elegance and comfort in the midst of top city attractions. Shopping and fun at the Magnificent Mile or Navy Pier, or a visit to the Lincoln Park Zoo are all within two miles. Our on-site restaurants, event room with natural light, and fitness center complete your stay.

The Hoxton, Chicago
Slightly more spacious than our snug rooms, the cosy room features a perfectly arranged king-size bed for ultimate comfort. Soft lighting and plush duvets make you feel at home the moment you arrive. Enjoy a walk-in rain shower and thoughtfully designed details throughout. It's the ideal retreat for relaxing and unwinding in style.

A polished, modern affair on iconic Michigan Ave.
Experience an upgraded stay at Le Méridien Essex Chicago, located on Michigan Ave in the city's heart. Our luxury hotel, surrounded by iconic attractions, offers modern rooms with stunning views of Grant Park, Lake Michigan, Buckingham Fountain, and the Museum Campus. We're committed to making your stay in the Loop unforgettable.
Popular amenities for Chicago hotels
Family-friendly hotels

Club Quarters Hotel Wacker at Michigan, Chicago

Family-Friendly Stay Near Joliet Mall and Downtown

Rare upscale Gold Coast boutique find

Relaxing Stay Downtown! Pets are Allowed

Myers Suite - The Plainfield Inn

Pet-friendly Property Near SkyDeck Chicago!

Staypineapple, An Iconic Hotel, The Loop

McCormick Suites by Slumber Stay | 2BR
Hotels with a pool

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

Comfort and Relaxation! Parking, Near Navy Pier

Find Your Oasis of a Peaceful Stay | Restaurant

Stay Downtown | Rooftop pool. Gym

Close to Oakbrook Center + On-site Dining & Pool

Minutes from Downtown | Free Breakfast & Parking

Perfect Destination! Onsite Bar and Restaurant!

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

Riu Plaza Chicago

2 Queen Bed Room

Stylish Room with Rooftop Lounge & City Views

Private Room in Theatre District

Close to O’Hare Airport + Free Breakfast & Shuttle

King Room in heart of Downtown

2 Queen Bedroom in Downton

Chicago's Magnificent Mile Stay + Dining & Gym
Destinations to explore
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- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Grant Park
- Navy Pier
- Soldier Field
- 875 North Michigan Avenue
- The Field Museum
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- Union Park
- University of Chicago
- Lincoln Park Zoo
- Chicago River Walk
- Frank Lloyd Wright Home and Studio
- Garfield Park Conservatory
- Washington Park Zoo
- Loyola University Chicago
- Indiana Dunes State Park
- Oak Street Beach
- Illinois Beach State Park
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