
Hotels in Chicago
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Top-rated hotels in Chicago
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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.

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.

Millennium Knickerbocker Hotel Chicago
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.

Riu Plaza Chicago
Deluxe king rooms are the perfect choice for a relaxing break in the exciting city of Chicago. Each room includes a shower, hairdryer, central heating, air conditioning, and an in room safe for your convenience. Enjoy added comforts like a small fridge, coffee maker, and a cozy sofa to unwind. An iron is also provided to keep you looking your best during 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.

Chicago Hotel Collection Ambassador Gold Coast
Standard queen features a queen bed and crib, blackout curtain, safe, coffee and tea maker, climate control, and signature bath amenities with walk-in shower. Enjoy workspace and easy access to the gym, bar, restaurant, and rooftop terrace for a comfortable, memorable stay.
Popular amenities for Chicago hotels
Family-friendly hotels

Club Quarters Hotel Wacker at Michigan, Chicago

Rare upscale Gold Coast boutique find

Close to Medinah Country Club + Breakfast. Kitchen

Relaxing Stay Downtown! Pets are Allowed

Myers Suite - The Plainfield Inn

Close to Riverwalk | Indoor Pool + Free Breakfast

The Allegro Royal Sonesta Hotel Chicago Loop

Pet-friendly Property Near SkyDeck Chicago!
Hotels with a pool

Level Chicago - Fulton Market

Comfort and Relaxation! Parking, Near Navy Pier

Stay Downtown | Rooftop pool. Gym

Close to Oakbrook Center + On-site Dining & Pool

LEVEL Chicago - Old Town

Find Your Oasis of a Peaceful Stay | Restaurant

Minutes from Downtown | Free Breakfast & Parking

Peaceful Retreat In Cook County | Restaurant
Other hotel holiday rentals

Queen Bed | Breakfast Included. No Cleaning Fee*

2 Queen Bed Room

Private Room in Theatre District

Close to O’Hare Airport + Free Breakfast & Shuttle

Riu Plaza Chicago

Millennium Knickerbocker Hotel Chicago

Near Magnificent Mile | Gym. Free Breakfast.

King Room in heart of Downtown
Quick stats about hotels in Chicago

Total holiday rentals
Explore 450 holiday rentals in Chicago

Nightly prices starting at
Chicago holiday rentals start at $26 SGD 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 & child-friendly amenities

Pet-friendly holiday rentals
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

Wifi availability
450 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
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- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Grant Park
- Navy Pier
- Soldier Field
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- The Field Museum
- Guaranteed Rate Field
- Union Park
- Lincoln Park Zoo
- Chicago River Walk
- Frank Lloyd Wright Home and Studio
- Garfield Park Conservatory
- Washington Park Zoo
- Indiana Dunes State Park
- Oak Street Beach
- Museum of Science and Industry
- Illinois Beach State Park
- Willis Tower
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