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

Total holiday rentals
Explore 240 holiday rentals in The Loop

Nightly prices starting at
The Loop holiday rentals start at $26 SGD per night before taxes and fees

Verified guest reviews
Over 5,840 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 120 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
210 properties have a dedicated workspace

Wifi availability
240 of The Loop holiday rentals include wifi access

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

4.6 Average rating
The Loop stays receive an average rating of 4.6 out of 5 from guests

Nearby attractions
The Loop’s top spots include Millennium Park, Shedd Aquarium and Willis Tower
Top-rated hotels in The Loop
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.

2 Queen Bedroom in Downton
Experience upscale accommodations & amenities in the heart of Chicago when you stay at Cambria Hotel. Located conveniently close to some 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.

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.

Club Quarters Hotel Central Loop, Chicago
Our standard room is designed for flexibility and comfort, featuring a comfortable bed with premium bedding, an ergonomic workspace, and ultra-fast free Wi-Fi. Enjoy convenient amenities like a Nespresso coffeemaker, smart TV, and multiple charging outlets for easy work or relaxation. The room is non-smoking, dog friendly, and includes C.O. Bigelow bathroom amenities. Yoga mats and resistance bands are available upon request for a well-rounded stay.

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.

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.

Millennium Knickerbocker Hotel Chicago, Standard...
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.

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.

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 The Loop hotels
Family-friendly hotels

The Champagne Lodge & Luxury Suites

2 Queen Bed Room in Theatre Dst

Rare upscale Gold Coast boutique find

Pet-friendly Property Near SkyDeck Chicago!

2 Queen Bed Room

Private Room in Theatre District

King Room in heart of Downtown

River North Stay | 1 Unit | Near Chicago Loop
Hotels with a pool

The Robey Hotel Double Queen Loft

Viceroy Chicago

Comfort and Relaxation! Parking, Near Navy Pier

Suite 501 | Stay One Chicago

The Robey Hotel Landmark Queen

Hotel - Jet Tub, King Bed, Bfast Included

Close to Oakbrook Center + On-site Dining & Pool

Close to O’Hare Airport + Free Breakfast & Shuttle
Other hotel holiday rentals

Hotel Felix

Club Quarters Hotel Central Loop, Chicago

Chicago Hotel Collection Ambassador Gold Coast

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

McCormick Suites by Slumber Stay | 2BR

Central Loop Hotel

Millennium Knickerbocker Hotel Chicago, Superior...
Destinations to explore
- Rentals with an accessible-height bed Chicago Loop
- Rentals with pools Chicago Loop
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- Flat rentals Chicago Loop
- Pet-friendly rentals Chicago Loop
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- Waterfront rentals Chicago Loop
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- Serviced apartment rentals Chicago Loop
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- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Grant Park
- Navy Pier
- Chicago River Walk
- Soldier Field
- 875 North Michigan Avenue
- Six Flags Great America
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- Shedd Aquarium
- The Field Museum
- Guaranteed Rate Field
- Union Park
- Lincoln Park Zoo
- University of Chicago
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- Museum of Science and Industry
- Illinois Beach State Park
- Willis Tower
- Loyola University Chicago
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