Holiday houses in South Loop, Chicago
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in South Loop, Chicago
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for South Loop, Chicago holiday rentals
Other great holiday rentals in South Loop, Chicago
Guest favourite
Guest suite in Bronzeville
4.94 out of 5 average rating, 155 reviewsBronzeville Beauty: Modern Style + Historic Charm
9–16 Sep
$285 NZD per night
Guest favourite
Apartment in Humboldt Park
4.98 out of 5 average rating, 107 reviewsHumboldt Park Loft
24–31 Oct
$274 NZD per night
Guest favourite
Guest suite in Chicago
4.93 out of 5 average rating, 172 reviewsBike the Lakefront from a Sleek Urban Retreat
1–8 Mar
$258 NZD per night
Guest favourite
Apartment in Lincoln Park
4.98 out of 5 average rating, 297 reviewsRedesigned Lower Level Studio in Historic Building
3–10 Oct
$331 NZD per night
Superhost
Apartment in Chicago
4.82 out of 5 average rating, 87 reviewsMcCormick Pl 420 friendly 1br/1ba parking/sleeps 4
16–23 Feb
$182 NZD per night
Guest favourite
Apartment in Chicago
4.79 out of 5 average rating, 19 reviewsCozy Condo near Downtown Chicago
8–15 Jan
$298 NZD per night
Guest favourite
Apartment in Chicago
4.97 out of 5 average rating, 61 reviewsLocation! Location! Location!
27 Jul – 3 Aug
$303 NZD per night
Guest favourite
Apartment in Near South Side
4.95 out of 5 average rating, 55 reviewsThe Executive's Escape (2BD/2BA)
16–23 Jan
$484 NZD per night
Quick stats about holiday rentals in South Loop, Chicago
Total rentals
420 properties
Rentals with a pool
110 properties have a pool
Pet-friendly rentals
120 properties allow pets
Family-friendly rentals
240 properties are a good fit for families
Total number of reviews
15K reviews
Nightly prices starting at
$17 NZD before taxes and fees
Destinations to explore
- Rentals with a fire pit South Loop
- Rentals with a washing machine and dryer South Loop
- Condo rentals South Loop
- Smoking-friendly rentals South Loop
- Rentals with lake access South Loop
- Apartment rentals South Loop
- Rentals with a patio South Loop
- Monthly Rentals South Loop
- Fitness-friendly rentals South Loop
- Rentals with an EV charger South Loop
- Rentals with a hot tub South Loop
- Rentals with outdoor seating South Loop
- Rentals with a fireplace South Loop
- Pet-friendly rentals South Loop
- Family-friendly rentals South Loop
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