Apartment holiday rentals in South Loop, Chicago
Find and book unique apartments on Airbnb
Top-rated apartment rentals in South Loop, Chicago
Guests agree: These apartments are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for South Loop, Chicago apartment rentals
Weekly apartment rentals
Apartment in Near North Side
4.9 out of 5 average rating, 372 reviewsGreat Location Studio in the Gold Coast!!
20 – 27 Dec
Apartment in Avondale
4.97 out of 5 average rating, 119 reviewsDesigner Avondale Attic
8 – 15 July
Apartment in Logan Square
4.93 out of 5 average rating, 208 reviewsCozy Private Coach House
2 – 9 Sept
Apartment in Chicago
4.84 out of 5 average rating, 130 reviewsPerfect Private Getaway in Perfect Pilsen
27 Sept – 4 Oct
Apartment in West Town
4.92 out of 5 average rating, 327 reviewsBright, Modern Apartment in a Vintage Greystone
14 – 21 Apr
Apartment in Lincoln Square
4.94 out of 5 average rating, 191 reviewsSpacious, light-drenched studio-private entrance!
14 – 21 July
Apartment in Pilsen Historic District
4.82 out of 5 average rating, 431 reviewsEclectic Artist Designed Sanctuary Heart of Pilsen
23 – 30 Sept
Apartment in Chicago
4.9 out of 5 average rating, 258 reviewsBright & Lofty Bucktown 1br
9 – 16 Dec
Private apartment rentals
Apartment in Chicago
4.95 out of 5 average rating, 124 reviewsCozy 2 bdrm near McCormick Place & Wintrust Arena
30 June – 7 July
Apartment in Cicero
4.98 out of 5 average rating, 204 reviewsCOZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
25 Apr – 2 May
Apartment in Near South Side
4.78 out of 5 average rating, 88 reviewsMcCormick Place Studio/parking/sleeps up to 4
15 – 22 Jan
Apartment in Chicago
4.79 out of 5 average rating, 19 reviewsCozy Condo near Downtown Chicago
23 – 30 Jan
Apartment in Chicago
4.97 out of 5 average rating, 62 reviewsLocation! Location! Location!
5 – 12 July
Apartment in Near South Side
4.89 out of 5 average rating, 57 reviewsMcCormick 2br/2ba Oasis Parking/Patio/Gym/sleeps 6
14 – 21 Feb
Apartment in Chicago
4.92 out of 5 average rating, 53 reviewsStunning Basement Apartment w/free street parking!
9 – 16 Nov
Apartment in Chicago
5.0 out of 5 average rating, 75 reviewsBright Cozy Modern-Chic Condo in Trendy West Town
6 – 13 Apr
Apartment rentals with a hot tub
Apartment in West Town
4.88 out of 5 average rating, 394 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
4 – 11 Sept
Apartment in Berwyn
4.91 out of 5 average rating, 204 reviews“Dream slice of urban homesteading.”
15 – 22 Oct
Apartment in The Loop
4.8 out of 5 average rating, 10 reviewsThe Areal Oasis
25 Oct – 1 Nov
Apartment in Logan Square
4.91 out of 5 average rating, 32 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
20 – 27 Apr
Apartment in Chicago
4.87 out of 5 average rating, 45 reviewsSpectacular Rooftop Getaway in Heart of City
25 Aug – 1 Sept
Apartment in West Town
4.88 out of 5 average rating, 42 reviewsCloud 9 | Presidential Penthouse Suite | The Iris
12 – 19 Nov
Apartment in West Rogers Park
4.86 out of 5 average rating, 21 reviewsSpacious Beautiful Condo
22 – 29 Oct
Apartment in Belmont Cragin
5.0 out of 5 average rating, 27 reviewsBelmont Pleasures - hot tub / arcade gaming room
7 – 14 Jan
Quick stats about apartment rentals in South Loop, Chicago
Total rentals
320 properties
Rentals with a pool
90 properties have a pool
Pet-friendly rentals
90 properties allow pets
Family-friendly rentals
190 properties are a good fit for families
Total number of reviews
10K reviews
Nightly prices starting at
$15 AUD before taxes and fees
Destinations to explore
- Serviced apartment rentals United States
- Apartment rentals United States
- Apartment rentals Chicago
- Apartment rentals Chicago
- Apartment rentals Downtown Chicago
- Apartment rentals Milwaukee
- Apartment rentals Illinois
- Rentals with a hot tub South Loop
- Condo rentals South Loop
- Family-friendly rentals South Loop
- Rentals with an EV charger South Loop
- Rentals with a fire pit South Loop
- Fitness-friendly rentals South Loop
- Rentals with outdoor seating South Loop
- Smoking-friendly rentals South Loop
- Monthly Rentals South Loop
- Rentals with a fireplace South Loop
- Rentals with lake access South Loop
- Rentals with a patio South Loop
- Pet-friendly rentals South Loop
- Rentals with a washing machine and dryer South Loop
- Apartment rentals Cook County
- 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