South Loop, Chicago vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in South Loop, Chicago
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
0 of 0 items showing
1 of 3 pages
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for South Loop, Chicago vacation rentals
Other great vacation rentals in South Loop, Chicago
Superhost
Home in West Lawn
4.93 out of 5 average rating, 29 reviewsFamily Friendly Duplex/9 min from MDW/Free Parking
Guest favorite
Apartment in West Town
4.85 out of 5 average rating, 126 reviewsCondo with private terrace, free WIFI and parking
Superhost
Apartment in Jefferson Park
4.86 out of 5 average rating, 14 reviewsCity Gem: Stylish 3BR for Urban Explorers
Guest favorite
Home in Logan Square
4.85 out of 5 average rating, 85 reviewsCalifornia Cottage/4br prime location Logan Square
Superhost
Apartment in Chicago Ridge
4.72 out of 5 average rating, 29 reviewsPeaceful two bedroom condo
Guest favorite
Apartment in Hermosa
4.95 out of 5 average rating, 79 reviewsChicago 3BR apt close to downtown w/pkg
Guest favorite
Apartment in Whiting
5 out of 5 average rating, 29 reviewsThe Standard- 1st floor
Guest favorite
Home in Riverdale
4.94 out of 5 average rating, 53 reviewsBeautiful , fully renovated
Quick stats about vacation rentals in South Loop, Chicago
Total rentals
460 properties
Nightly prices starting at
R189 ZAR before taxes and fees
Total number of reviews
19K reviews
Family-friendly rentals
250 properties are a good fit for families
Pet-friendly rentals
140 properties allow pets
Rentals with a pool
110 properties have a pool
Destinations to explore
- Pet-friendly rentals South Loop
- Rentals with a fireplace South Loop
- Rentals with a patio South Loop
- Rentals with a fire pit South Loop
- Monthly Rentals South Loop
- Fitness-friendly rentals South Loop
- Condo rentals South Loop
- Rentals with an EV charger South Loop
- Smoking-friendly rentals South Loop
- Rentals with a washer and dryer South Loop
- Family-friendly rentals South Loop
- Apartment rentals South Loop
- Rentals with lake access South Loop
- Rentals with outdoor seating South Loop
- Rentals with a hot tub South Loop
- Rentals with pools South Loop
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom