Vacation rentals in South Loop, Chicago
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Top-rated vacation rentals in South Loop, Chicago
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for South Loop, Chicago vacation rentals
Other great vacation rentals in South Loop, Chicago
Guest favourite
Apartment in Near South Side
4.87 out of 5 average rating, 163 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Guest favourite
Apartment in Chicago
4.97 out of 5 average rating, 67 reviewsLocation! Location! Location!
Guest favourite
Apartment in Near South Side
4.83 out of 5 average rating, 23 reviewsCozy Condo near Downtown Chicago
Guest favourite
Guest suite in West Loop
4.92 out of 5 average rating, 85 reviewsCozy one-bedroom suite in the heart of West Loop
Guest favourite
Apartment in Near South Side
4.94 out of 5 average rating, 18 reviewsMcCormick 2B/2Ba for up to 6 guests w Opt Parking
Guest favourite
Apartment in Chicago
4.93 out of 5 average rating, 54 reviewsStunning Basement Apartment w/free street parking!
Superhost
Apartment in Near South Side
4.89 out of 5 average rating, 36 reviewsMcCormick Place 420 friendly 3BR/2BA/opt parking
Guest favourite
Apartment in Little Italy
4.94 out of 5 average rating, 36 reviewsNewly Renovated 1BD near West Loop & Little Italy
Quick stats about vacation 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
$14 CAD before taxes and fees
Destinations to explore
- Monthly Rentals South Loop
- Rentals with an EV charger South Loop
- Condo rentals South Loop
- Rentals with lake access South Loop
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- Family-friendly rentals South Loop
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- Pet-friendly rentals South Loop
- Rentals with a washer and dryer South Loop
- Smoking-friendly rentals South Loop
- Rentals with outdoor seating South Loop
- Rentals with a patio South Loop
- Rentals with a hot tub South Loop
- Fitness-friendly rentals South Loop
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