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
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Popular amenities for South Loop, Chicago apartment rentals
Weekly apartment rentals
Apartment in Chicago
4.92 out of 5 average rating, 327 reviewsBright, Modern Apartment in a Vintage Greystone
2–9 Mar
Apartment in Logan Square
4.9 out of 5 average rating, 258 reviewsBright & Lofty Bucktown 1br
18–25 Jan
Apartment in Wrigleyville
4.93 out of 5 average rating, 187 reviewsTaj Ma-small at Wrigley
23 Feb – 2 Mar
Apartment in Pilsen Historic District
4.82 out of 5 average rating, 431 reviewsEclectic Artist Designed Sanctuary Heart of Pilsen
21–28 Oct
Apartment in Chicago
4.84 out of 5 average rating, 130 reviewsPerfect Private Getaway in Perfect Pilsen
24–31 Jul
Apartment in Chicago
4.84 out of 5 average rating, 176 reviewsLa Cottage
25 Oct – 1 Nov
Apartment in Gold Coast
4.89 out of 5 average rating, 140 reviewsCharming Gold Coast One-Bedroom Near Downtown!
7–14 Jan
Apartment in Lincoln Square
4.94 out of 5 average rating, 191 reviewsSpacious, light-drenched studio-private entrance!
28 Jul – 4 Aug
Private apartment rentals
Apartment in Uptown
4.96 out of 5 average rating, 267 reviewsCozy loft in Chicago's Uptown
22–29 Oct
Apartment in West Town
4.93 out of 5 average rating, 186 reviewsSpacious & Clean Ukrainian Village 2 Bedroom!
30 Jan – 6 Feb
Apartment in Chicago
4.97 out of 5 average rating, 62 reviewsLocation! Location! Location!
22–29 Jul
Apartment in Near South Side
4.79 out of 5 average rating, 19 reviewsCozy Condo near Downtown Chicago
23–30 Jan
Apartment in Near South Side
4.88 out of 5 average rating, 78 reviewsMcCormick 2B/2Ba w opt parking for up to 6 guests
13–20 Feb
Apartment in West Town
5.0 out of 5 average rating, 75 reviewsBright Cozy Modern-Chic Condo in Trendy West Town
22–29 Jan
Apartment in Chicago
4.92 out of 5 average rating, 53 reviewsStunning Basement Apartment w/free street parking!
14–21 Sep
Apartment in Bridgeport
5.0 out of 5 average rating, 21 reviewsUrban Cottage
22–29 Oct
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
24–31 Oct
Apartment in Berwyn
4.91 out of 5 average rating, 204 reviews“Dream slice of urban homesteading.”
13–20 Sep
Apartment in West Loop
4.87 out of 5 average rating, 106 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
23 Feb – 2 Mar
Apartment in The Loop
4.8 out of 5 average rating, 10 reviewsThe Areal Oasis
4–11 Jul
Apartment in Logan Square
4.91 out of 5 average rating, 32 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
15–22 Nov
Apartment in West Rogers Park
4.86 out of 5 average rating, 21 reviewsSpacious Beautiful Condo
14–21 Oct
Apartment in Chicago
4.87 out of 5 average rating, 45 reviewsSpectacular Rooftop Getaway in Heart of City
25 Aug – 1 Sep
Apartment in Chicago
5.0 out of 5 average rating, 26 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
$17 NZD before taxes and fees
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