Holiday houses in The Loop

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in The Loop

  • Total holiday rentals

    Explore 1,230 holiday rentals in The Loop

  • Nightly prices starting at

    The Loop holiday rentals start at $69 NZD per night before taxes and fees

  • Verified guest reviews

    Over 29,840 verified reviews to help you choose

  • Family-friendly holiday rentals

    380 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 560 rentals that welcome pets

  • Holiday rentals with a pool

    550 properties feature pools

  • Rentals with dedicated workspaces

    810 properties have a dedicated workspace

  • Wi-Fi availability

    1,200 of The Loop holiday rentals include Wi-Fi 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.

1 of 1 pages1 / 1
Guest favourite
Apartment in The Loop
4.95 out of 5 average rating, 100 reviews

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

Guest favourite
Apartment in The Loop
4.92 out of 5 average rating, 38 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

Top Guest favourite
Apartment in West Loop
4.95 out of 5 average rating, 111 reviews

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.

A modern living room is presented with a gray sofa flanked by two white chairs. An abstract painting in a gold and blue palette adorns the wall. Natural light streams in, illuminating the soft area rug with a subtle pattern, while an elegant floor lamp stands to the side.
Apartment in The Loop
4.8 out of 5 average rating, 88 reviews

Central downtown home in Loop

Location and location! Cozy, renovated downtown apartment with $1000+ high end bed is centrally located right in the loop. Not only are you right by the Bean and Grant Park, you’re only a couple blocks away from the Lake!! Walkable distance to Millennium Park and all the beautiful tourist places in downtown. This special place is close to everything and in the best neighborhood, making it easy to plan your visit. Note** noise from outside. This is a sample unit. You will be getting similar.

A modern high-rise building is showcased, featuring a glass and brick exterior. The building has multiple stories with large windows, providing a contemporary look. Surrounding trees are visible along the street, contributing to the urban landscape.
Apartment in The Loop
4.81 out of 5 average rating, 570 reviews

Kasa | 2BD Near McCormick Place | 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.
Apartment in Downtown Chicago
4.81 out of 5 average rating, 1,019 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
Condo in The Loop
4.89 out of 5 average rating, 175 reviews

Downtown Park #11 - Mich Ave PH | 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 Queen 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.
Apartment in The Loop
4.89 out of 5 average rating, 297 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.
Apartment in The Loop
4.91 out of 5 average rating, 224 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!

Guest favourite
Apartment in Downtown Chicago
4.98 out of 5 average rating, 213 reviews

Elegant Suite in Gold Coast

Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, this generous one-bedroom apartment is perfectly situated in the middle of the action for your Chicago adventure. ***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.***

Superhost
Apartment in Downtown Chicago
4.79 out of 5 average rating, 163 reviews

Level ◆ Brand New Luxe One Bedroom

Designed with you in mind, our One Bedroom Suites range from 560 – 698 sq ft of spacious living space boasting fully-equipped kitchen, comfortable living area, spa-inspired bathroom, bedroom with king bed and open-air balcony. Perfect for couples and corporate travelers alike, all suites also feature in-suite laundry, premium appliances, flat-screen TV with cable, complimentary WiFi and local calling. Welcome to the suite life.

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.
Apartment in The Loop
4.83 out of 5 average rating, 209 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?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$255 NZD$259 NZD$310 NZD$341 NZD$424 NZD$498 NZD$497 NZD$440 NZD$419 NZD$386 NZD$304 NZD$274 NZD
Avg. temp-3°C-1°C4°C10°C16°C22°C25°C24°C20°C13°C6°C0°C

Destinations to explore

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