
Apartment vacation rentals in The Loop
Find and book unique apartments on Airbnb
Quick stats about apartment rentals in The Loop

Total vacation rentals
Explore 670 vacation rentals in The Loop

Nightly prices starting at
The Loop vacation rentals start at €34 per night before taxes and fees

Verified guest reviews
Over 18,140 verified reviews to help you choose

Family-friendly vacation rentals
270 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 340 rentals that welcome pets

Vacation rentals with a pool
400 properties feature pools

Rentals with dedicated workspaces
370 properties have a dedicated workspace

Wi-Fi availability
660 of The Loop vacation rentals include wi-fi access

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

4.7 Average rating
The Loop stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
The Loop's top spots, include Millennium Park, Shedd Aquarium, and Willis Tower
Top-rated apartment rentals in The Loop
Guests agree: these apartments are highly rated for location, cleanliness, and more.

LIVN Millennium Park Downtown Chicago 1 BR
Experience the best of Chicago from this stylish, newly renovated 1-bedroom at 19 S Wabash Ave. Perfectly located in the heart of downtown, you'll be steps away from iconic Millennium Park, the vibrant shops of Michigan Avenue, and a world of dining options. This 1 bedroom offers modern comfort with a fully equipped kitchen, including a refrigerator, dishwasher, and coffee maker, plus the convenience of an in-unit washer and dryer, making it ideal for both short getaways and extended stays. Enjo

The Metropolitan Retreat (Fitness Center • Sauna)
Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 2 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. Within walking distance are world famous attractions including: Millennium Park, The Bean, Navy Pier, Riverwalk, Soldier Field, The Field Museum, and more. Additionally, guests are merely a couple blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city.

Chic 2BR Gem with Fireplace
Discover urban luxury in our 2BR, 2BA Gold Coast haven. This stylish apartment boasts a warm fireplace, sleek granite countertops, and a cozy layout. Immerse yourself in city living at its finest, right in the heart of Chicago's prestigious Gold Coast neighborhood. ***Please note that from March until the end of September 2026, there will be construction on the upper floors of the building that may cause noise during the daytime hours. Construction will not be happening on the weekends.***

Fulton House #1 (2bd/ 1ba)
Unique & stylishly designed by Chicago's own Outline Interiors, this highly sought after location is for those that want to stay on a calm side street around the corner from city's best, award-winning restaurants and trendiest shopping. The fully-serviced apartment has the business-travel amenities you want: ultra speed wifi, work stations, top tier dining options within steps of the front door, Nespresso coffee, bottled water, washer/dryer. First-come parking next door: $20/nt or $200/mo.

Kasa | Views from your Private Balcony | Chicago
When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

The South Loop Reserve I Sleep 6 I Top Rated
Modern & ultra spacious 2-bedroom loft in Chicago's South Loop. Central location to Grant Park, Soldier Field, Museums, McCormick Place and more! With a walk & transit score of 97, enjoying Chicago's fantastic restaurants, bars, and shopping options is a breeze. Our loft gets incredible natural light, has luxuriously tall ceilings and plenty of room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide.

Spacious & Stylish 2BR-2BA Apt Steps from The Bean
Enjoy this comfy, renovated and super spacious 2BR and 2BA apartment in the heart of Chicago's Loop with views of Lake Michigan. Surrounded by the most popular stores and restaurants, this unbeatable location is less than a one-minute walk to Michigan Ave, Millennium Park, State St. Shopping, The Chicago Theatre and Chicago’s landmark, ‘The Bean'. It is an ideal location to move around in public transportation, as all CTA lines and plenty of bus lines are just within two blocks!

Lavish 2BR/2BA Loft I Next to Grant Park & Museums
Enjoy Chicago in our modern & spacious 2-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!

Urban Chic Apartment by the Magnificent Mile
Ideally located just half a block from Michigan Avenue, this bright and open 3rd floor apartment boasts thoughtfully appointed rooms for your comfort so will have everything you need to enjoy your stay in style! PLEASE NOTE: 3rd floor walk up (NO ELEVATOR) There is a small neighborhood bar on the second floor of the building. They are respectful of our neighbors, however they do play music which can be heard in the living room but rarely in the bedrooms.

Spacious Downtown 3BR with Free Parking
A beautiful, modern, three bedroom two bath apartment located in the heart of Fulton Market in downtown Chicago. You'll have the whole space to yourself with easy access to some of the best restaurants in the city, a free parking space on premise, and nearby access to public transportation to quickly get around the city. The interior is recently renovated with new furnishings, and provides a beautiful space to relax and recharge between outings.

Pilsen Modern Chic Retreat
Welcome to your perfect getaway! This stunning 2-bedroom home is the epitome of modern chic; offering an unforgettable blend of style and comfort. Designed for up to 6 guests, the space is crafted with thoughtful architectural details and an eye for eclectic decor. Located in the heart of Pilsen, known for its vibrant art scene, trendy restaurants, & local culture, you'll be perfectly situated to explore everything Chicago has to offer.

Splendid Corner 3BR in the Loop | City Views
Stylish 1,300+ square foot corner apartment with 12 foot tall ceilings, massive windows, an open layout, and fabulous city views in multiple directions. This dramatic light-filled three bedroom, two bathroom space is perfect for groups looking for a luxurious escape in the sky in the heart of downtown Chicago. Centrally located in a historic building close to everything you want to visit, this is the best location in the city!
Popular amenities for The Loop apartment rentals
Weekly apartment rentals

Explore Lincoln Park from a Polished Apartment

Great Location!!-12

Dtown Penthouse 11+Parking, Gym, Pvt Patio

FREE PARKING Large 2BR2BA by Millenium Park

Luxury Penthouse Loft w/Terrace 507 | River North

South Loop Studio Hotel (304)

Little Italy Historic Restoration Row House

Modern 3BR Apartment Near North Ave Shops
Private apartment rentals

Pilsen Prism: Sun-Drenched 3BR + Parking

Kasa | 2BD Near McCormick Place | South Loop

Sentral Premium 2BR Apt South Loop Chicago

Plymouth Collection: Top Floor w/ Rooftop & Lobby

Plymouth Collection: 2BD with Lobby, Gym, Rooftop

Boulevard Stays Walk Everywhere! 5 mins to Magnifi

European Coziness in Bronzeville

The Landing @ South Loop
Apartment rentals with a hot tub

Checkerboard Studio, Private Outdoor Hot Tub, Yard

Top Floor Views + Central Comfort

Level One Bedroom Suite | Fulton Market

Luxury 3BD Penthouse – Private Patio+Skyline Views

Comfy Near Downtown Chicago

Luxury South Loop Apt

The Velvet Manor | Luxe 3BR • Jacuzzi • Garage

Spacious and Ideally located in the Lakeview area
When is the best time to visit The Loop?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €129 | €131 | €170 | €193 | €253 | €306 | €234 | €213 | €189 | €183 | €154 | €139 |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Destinations to explore
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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
- University of Chicago
- The Field Museum
- Shedd Aquarium
- Humboldt Park
- Loyola University Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Union Park
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- Frank Lloyd Wright Home and Studio
- Donald E Stephens Convention Center
- Byline Bank Aragon Ballroom
- Washington Park Zoo
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