Holiday houses in South Loop, Chicago
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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
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Popular amenities for South Loop, Chicago holiday rentals
Other great holiday rentals in South Loop, Chicago
Guest favourite
Apartment in Chicago
4.97 out of 5 average rating, 64 reviewsLocation! Location! Location!
Superhost
Apartment in Near South Side
4.79 out of 5 average rating, 67 reviewsMcCormick Place Studio/parking/sleeps up to 4
Guest favourite
Apartment in Near South Side
4.79 out of 5 average rating, 19 reviewsCozy Condo near Downtown Chicago
Guest favourite
Guest suite in West Loop
4.92 out of 5 average rating, 84 reviewsCozy one-bedroom suite in the heart of West Loop
Guest favourite
Apartment in Near South Side
4.95 out of 5 average rating, 56 reviewsThe Executive's Escape (2BD/2BA)
Guest favourite
Apartment in Bridgeport
5.0 out of 5 average rating, 23 reviewsUrban Cottage
Guest favourite
Apartment in Chicago
4.92 out of 5 average rating, 53 reviewsStunning Basement Apartment w/free street parking!
Guest favourite
Condo in Lake View
4.96 out of 5 average rating, 25 reviewsChic & Comfy • Close to Wrigley
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
$16 NZD before taxes and fees
Destinations to explore
- Rentals with a hot tub South Loop
- Family-friendly rentals South Loop
- Pet-friendly rentals South Loop
- Monthly Rentals South Loop
- Rentals with a fire pit South Loop
- Condo rentals South Loop
- Rentals with an EV charger South Loop
- Fitness-friendly rentals South Loop
- Rentals with a washing machine and dryer South Loop
- Rentals with lake access South Loop
- Rentals with a fireplace South Loop
- Smoking-friendly rentals South Loop
- Rentals with a patio South Loop
- Apartment rentals South Loop
- Rentals with outdoor seating South Loop
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