Apartment holiday rentals in South Loop, Chicago
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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
Flat in Chicago
4.98 out of 5 average rating, 131 reviewsModern Apt with style & comfort in Pilsen Chicago
26 Jul – 2 Aug
Flat in Chicago
4.84 out of 5 average rating, 175 reviewsThe Cottage
1–8 Oct
Flat in Lincoln Park
4.99 out of 5 average rating, 194 reviewsExplore Lincoln Park from a Polished Apartment
22 Feb – 1 Mar
Flat in West Town
4.89 out of 5 average rating, 473 reviewsiKlektik House Chicago / Robin
22–29 Sep
Flat in Gold Coast
4.89 out of 5 average rating, 140 reviewsCharming Gold Coast One-Bedroom Near Downtown!
8–15 Jan
Flat in Chicago
4.94 out of 5 average rating, 265 reviewsCozy City Living-Near Downtown-Food-Train
9–16 Sep
Flat in The Loop
4.88 out of 5 average rating, 113 reviewsLovely 1-bedroom serviced apartment near Museums!
1–8 Jul
Flat in Pilsen Historic District
4.82 out of 5 average rating, 431 reviewsEclectic Artist Designed Sanctuary Heart of Pilsen
21–28 Oct
Private apartment rentals
Flat in Chicago
4.85 out of 5 average rating, 273 reviewsHUGE|3br/2ba/Near DT/Free Parking/WI-FI/Pilsen
18–25 Nov
Flat in Lincoln Square
4.81 out of 5 average rating, 125 reviewsTranquil & Airy 1BR Apt in Lincoln Square
8–15 May
Flat in Avondale
4.97 out of 5 average rating, 118 reviewsDesigner Avondale Attic
22–29 Jul
Flat in West Loop
4.99 out of 5 average rating, 355 reviewsPeaceful River West Apt with free parking
7–14 Jun
Flat in Roscoe Village
4.96 out of 5 average rating, 238 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
19–26 Nov
Flat in Edgewater
4.99 out of 5 average rating, 104 reviewsNewly Renovated, Spacious 2BR in Andersonville
7–14 Dec
Flat in Near South Side
4.79 out of 5 average rating, 19 reviewsCozy Condo near Downtown Chicago
8–15 Jan
Flat in Chicago
4.97 out of 5 average rating, 61 reviewsLocation! Location! Location!
27 Jul – 3 Aug
Apartment rentals with a hot tub
Flat in West Town
4.88 out of 5 average rating, 394 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
24–31 Oct
Flat in Berwyn
4.91 out of 5 average rating, 203 reviews“Dream slice of urban homesteading.”
3–10 Oct
Flat in The Loop
5.0 out of 5 average rating, 7 reviewsThe Downtown Oasis (2BD / 2BA)
10–17 Feb
Flat in Logan Square
4.91 out of 5 average rating, 32 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
25 Nov – 2 Dec
Flat in West Town
4.88 out of 5 average rating, 42 reviewsCloud 9 | Presidential Penthouse Suite | The Iris
24 Feb – 3 Mar
Flat in Chicago
4.87 out of 5 average rating, 45 reviewsSpectacular Rooftop Getaway in Heart of City
29 Jun – 6 Jul
Flat in Belmont Cragin
5.0 out of 5 average rating, 26 reviewsBelmont Pleasures - hot tub / arcade gaming room
17–24 Feb
Flat in West Loop
5.0 out of 5 average rating, 10 reviewsSkyline Oasis: City & Lake Views
20–27 Sep
Quick stats about flat 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
10T reviews
Nightly prices starting at
₹834 before taxes and fees
Destinations to explore
- Flat rentals United States
- Serviced apartment rentals United States
- Flat rentals Chicago
- Flat rentals Chicago
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- Flat rentals Illinois
- Rentals with a firepit South Loop
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- Flat rentals Cook County
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