Apartment holiday rentals in South Loop

Find and book unique apartments on Airbnb

Quick stats about flat rentals in South Loop

  • Total holiday rentals

    Explore 380 holiday rentals in South Loop

  • Nightly prices starting at

    South Loop holiday rentals start at $51 SGD per night before taxes and fees

  • Verified guest reviews

    Over 17,120 verified reviews to help you choose

  • Family-friendly holiday rentals

    240 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 100 rentals that welcome pets

  • Holiday rentals with a pool

    110 properties feature pools

  • Rentals with dedicated workspaces

    260 properties have a dedicated workspace

  • Wifi availability

    380 of South Loop holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across South Loop rentals

  • 4.7 Average rating

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

Top-rated apartment rentals in South Loop

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

1 of 1 pages1 / 1
Top guest favourite
A rooftop pool area features a long, inviting pool bordered by lounge chairs in various colors. Sunlit trees are visible nearby, and the backdrop consists of modern high-rise buildings, creating a vibrant urban atmosphere.
Flat in Downtown Chicago
4.93 out of 5 average rating, 108 reviews

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.

Top guest favourite
Flat in West Loop
4.95 out of 5 average rating, 101 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.

Guest favourite
Flat in West Side
4.91 out of 5 average rating, 179 reviews

Unmatched Urban Retreat Close to 18th Strip & Loop

This stylish Airbnb in the very popular Pilsen neighborhood is perfect for small and large travel groups. There are 2 bedrooms with queen size beds, and the couch folds out for an additional sleeping area. The 2 full bathrooms will have everything you need to get ready to hit the town. The tall ceilings make this space for larger than life, and the unique décor gives this Airbnb a great urban feel. The fully equipped kitchen and updated appliances are perfect for those quiet nights in.

Superhost
A bright bedroom features a spacious bed with crisp white linens, complemented by an abstract wall art piece. A wooden nightstand with a lamp is positioned beside the bed. Large windows provide natural light, showcasing views of the city beyond.
Flat in Downtown Chicago
4.81 out of 5 average rating, 294 reviews

Kasa | Explore the Neighborhood-Mag Mile | 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
Flat in Downtown Chicago
4.94 out of 5 average rating, 226 reviews

South Loop 3BD 2BA Condo with Balcony and Parking

Stay in the heart of Chicago’s South Loop at this spacious 3-bedroom, 2-bath condo on Michigan Avenue. Enjoy easy access to Grant Park, Museum Campus, Soldier Field, McCormick Place, and the Lakefront Trail, with CTA trains and buses just steps away. This modern, walkable home features updated bathrooms and kitchen with new fixtures, hardwood floors throughout, a nice front deck, and an in-unit full-sized washer and dryer—perfect for families, groups, or business travelers.

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, 284 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, 216 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!

Top guest favourite
A modern kitchen features sleek black cabinetry and appliances, complemented by a contrasting white countertop. Stylish stools are arranged around a small kitchen island. The wall is adorned with a framed painting, while decorative items are displayed on open shelves above the countertop.
Flat in West Side
4.88 out of 5 average rating, 319 reviews

Spectacular Pilsen Studio for 2!

This chic studio in the heart of Pilsen is the perfect space to kick back and relax during your visit to the Windy City! The vibrant neighborhood always has something to offer to any type of traveler, and it's a quick trip to see most of the iconic Chicago sights. Easily walk to historic Thalia Hall, or drive to the Loop in just 5 minutes! You'll love the thoughtful touches and modern decor in the apartment, as well as the bright and welcoming main space.

Top guest favourite
A modern kitchen is showcased, featuring sleek cabinetry in dark tones and stainless steel appliances. An island with a light countertop provides ample space for meal preparation. Natural light enters through large windows, brightening the inviting atmosphere of the open layout.
Flat in West Side
4.95 out of 5 average rating, 112 reviews

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.

Guest favourite
Flat in Downtown Chicago
4.98 out of 5 average rating, 201 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 July 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
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
4.84 out of 5 average rating, 202 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!

Guest favourite
A spacious bedroom features large floor-to-ceiling windows, allowing natural light to fill the room. A large bed with neutral bedding is complemented by a contemporary desk and chair setup, which is arranged near a wood-framed lamp. A subtle area rug lies beneath the bed.
Flat in Downtown Chicago
4.9 out of 5 average rating, 133 reviews

50th Floor Mag Mile Views, Balcony, Pool, Gym

The Penthouses at Grand Plaza PH#12: Towering 50 stories above Downtown Chicago, this luxury unit features floor-to-ceiling windows and breathtaking skyline views. Enjoy sunsets, unmatched location, and true urban living. Walk Score of 100 with a grocery store in the building. Amenities include a fitness center, outdoor pool, kitchens, and business center. The city is at your feet—experience Chicago in style.

Popular amenities for South Loop apartment rentals

When is the best time to visit South Loop?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$171 SGD$192 SGD$234 SGD$245 SGD$300 SGD$321 SGD$336 SGD$319 SGD$285 SGD$333 SGD$247 SGD$215 SGD
Avg. temp-3°C-1°C4°C10°C16°C22°C25°C24°C20°C13°C6°C0°C
  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. South Loop
  7. Flat rentals