Holiday rentals in The Loop

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Quick stats about holiday rentals in The Loop

  • Total holiday rentals

    Explore 1,120 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 28,470 verified reviews to help you choose

  • Family-friendly holiday rentals

    380 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 550 rentals that welcome pets

  • Holiday rentals with a pool

    510 properties feature pools

  • Rentals with dedicated workspaces

    720 properties have a dedicated workspace

  • Wifi availability

    1,090 of The Loop holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Gym and BBQ grill 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 holiday rentals in The Loop

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Flat in The Loop
4.97 out of 5 average rating, 31 reviews

Upscale High-Rise Apt · Rooftop Pool + Views

Stay in this brand-new 2025 apartment with luxury amenities. Perfect for work or leisure, it offers everything you need for a comfortable stay. Building Amenities: - 24/7 concierge & secure entry - Rooftop pool & gym with skyline views - Rooftop lounge with a fireplace - Steps from grocery stores & restaurants Unit Highlights: - Stunning views of the city - Black-out curtains & roller shades - Work from home space - In-unit washer & dryer - Fully equipped kitchen - Fast WiFi - Modern design

The exterior of a modern high-rise building is visible, featuring large glass windows and a curved architectural design. Surrounding trees line the street, creating a blend of urban and natural elements. The image showcases the building's height against a clear blue sky.
Flat in The Loop
4.79 out of 5 average rating, 370 reviews

Kasa | Studio, Walk to Grant Park | South Loop

It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking distance of the Museum Campus, McCormick Place Center, and a variety of restaurants and shops. Our Kasas are the best choice for your trip to the Windy City with our spacious floorplans, full kitchen, laundry facilities, and parking. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text, phone, or chat, and a Virtual Front Desk accessed via mobile device.

Superhost
A serene bedroom features a spacious bed with crisp white linens and a light gray upholstered headboard. Natural light flows through large windows, illuminating the neutral walls and wood flooring. A small bedside table with a decorative lamp adds a touch of elegance to the space.
Flat in Downtown Chicago
4.81 out of 5 average rating, 1,009 reviews

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.

Guest favourite
A spacious rooftop deck is featured, showcasing a sectional sofa and colorful lounge chairs. A barbecue grill is positioned nearby, surrounded by planters filled with vibrant flowers. The skyline of Chicago and a glimpse of Lake Michigan are visible in the background under a clear blue sky.
Flat in The Loop
4.84 out of 5 average rating, 128 reviews

Downtown Mich Ave #10 | gym+rooftop

Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Guests love staying with us because: -Central Location on Grant Park (no car needed!) -FAST WIFI -En-suite Laundry -Did we mention the Lake & Park are outside our front door? -Comfy Double bed -Loft style bedroom -Shared Rooftop Deck stunning views -Gym -3 blocks from Red "L" subway -Close to Grant Park, The Bean, Soldier Field, Museums If you are looking for a special place, you've found it!

Guest favourite
A spacious living area is highlighted by large windows that provide ample natural light. A contemporary sofa faces a round black table, complemented by a vibrant red area rug. A striking mural adorns the wall behind the seating, adding a bold artistic touch to the space.
Flat in The Loop
4.89 out of 5 average rating, 292 reviews

1BR South Loop Loft I SuperHost + Top Rated!

Enjoy Chicago in our modern & spacious 1-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!

Top guest favourite
A spacious bedroom features a king bed with a memory foam mattress centered against a decorative wall panel. Two potted plants add greenery to the room, with modern pendant lights providing illumination. Large windows allow natural light to fill the space, complemented by a comfortable chair and a mirrored wardrobe.
Flat in The Loop
4.91 out of 5 average rating, 223 reviews

Lovely 1-bedroom serviced apartment near Museums!

Enjoy Chicago in our modern & spacious 1-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!

Flat in The Loop
4.83 out of 5 average rating, 6 reviews

Plymouth Collection: 2BD with Lobby, Gym, Rooftop

Welcome to The Plymouth Chicago, a historic 1899 landmark in the heart of Printers Row. Beautifully renovated in 2018 and thoughtfully redesigned in 2026, this stylish studio blends classic Chicago architecture with modern comfort. Enjoy a full kitchen, cozy living area, and in-unit laundry—perfect for longer stays. Play pool in the lobby, head up to the rooftop to grill, or workout in the gym. Just minutes from all Chicago attractions, it’s an ideal home base!

Top guest favourite
The living and dining area is designed with high ceilings and an open layout. A sofa is paired with a modern armchair, while a wooden dining table is surrounded by stylish chairs. Large windows bring in natural light, highlighting warm wood floors and minimal decor.
Flat in Downtown Chicago
4.94 out of 5 average rating, 289 reviews

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.

Top guest favourite
A modern living area is featured, showcasing a comfortable grey sofa and a light-colored coffee table. A dining space with dark wood chairs is visible. Natural light is allowed in through multiple windows, highlighting the blue accent wall and green foliage outside.
Flat in Wicker Park
5 out of 5 average rating, 12 reviews

Perfect Wicker Park Stay

Centrally located in Chicago’s beautiful Wicker Park/Bucktown neighborhood, this condo is in the perfect location to enjoy all of the shopping, dining, and night life the area has to offer. The spacious private balcony offers skyline views. Also conveniently located by Chicago’s CTA Damen Blue Line allowing easy access to and from Ohare and Chicago’s Magnificent Mile and Theatre District. Steps away from Olivia’s Market for all food/drink needs.

Arlo Chicago
4.84 out of 5 average rating, 166 reviews

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.

Guest favourite
Flat in West Loop
4.86 out of 5 average rating, 124 reviews

LIVN West Loop Chicago Queen Studio Apartment

Experience modern city living at LIVN West Loop Chicago, a stylish loft-style apartment studio at 555 W Jackson Blvd in one of the city’s most connected neighborhoods. This newly renovated studio features a full kitchen, in-unit washer and dryer, and clean, modern interiors. Walk to Union Station and Willis Tower. You are minutes from top dining, offices, and transit, ideal for business trips, weekend stays, or longer visits.

Superhost
A bright living area features large windows that provide panoramic city views. A comfortable gray sofa is positioned across from a 50" smart TV, with stylish accent chairs and a round coffee table nearby. Greenery adds a touch of nature to the space.
Flat in The Loop
4.83 out of 5 average rating, 204 reviews

Stunning Corner 2BR in the Loop | City & Lake View

Dramatic 1,250+ square foot corner apartment with 12 foot tall ceilings, massive windows, and panoramic city and lake views in multiple directions. This stylish light-filled two bedroom, two bathroom space is perfect for groups looking for a luxurious getaway 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 holiday rentals

When is the best time to visit The Loop?

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Avg. price$191 SGD$194 SGD$233 SGD$256 SGD$318 SGD$374 SGD$372 SGD$330 SGD$314 SGD$290 SGD$228 SGD$206 SGD
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Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. Chicago Loop