South Side vacation rentals
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Top-rated vacation rentals in South Side
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
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Popular amenities for South Side vacation rentals
Other great vacation rentals in South Side
Cottage in Gary
4.97 out of 5 average rating, 120 reviewsNeon Dunes Vista Beachfront Cottage
Home in Pilsen Historic District
4.95 out of 5 average rating, 328 reviewsGet Cozy at a Powder-Blue Residence in the Heart of Pilsen
Tiny home in Burr Ridge
4.92 out of 5 average rating, 253 reviewsLess is more! Pet friendly Tiny Home near Chicago!
Apartment in Pilsen Historic District
4.89 out of 5 average rating, 249 reviewsModern
Apartment in Chicago
4.84 out of 5 average rating, 177 reviewsThe Cottage
Guest suite in Chicago
4.83 out of 5 average rating, 208 reviewsVintage Suite Home Chicago by Sox/Park/Transit
Guest suite in Bridgeport
4.96 out of 5 average rating, 185 reviewsClean, Cozy, Comfortable Studio Near Downtown
Guest suite in Chicago
4.9 out of 5 average rating, 171 reviewsChicago Living: Your Home Away From Home
Other great vacation rentals in South Side
Guest suite in Chicago
4.98 out of 5 average rating, 114 reviewsGorgeous Studio 15 Minutes From Ohare!
Cabin in Griffith
4.9 out of 5 average rating, 164 reviewsBeautiful Rustic Cabin for Two!
Home in Chicago
4.91 out of 5 average rating, 92 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Vacation home in Chicago
4.96 out of 5 average rating, 45 reviewsUChicago Luxurious King Suite Lakefront
Apartment in Chicago
4.97 out of 5 average rating, 30 reviewsTravel To Chicago New City
Apartment in Chicago
4.9 out of 5 average rating, 73 reviewsGround-Level Speakeasy: 1BR-1.5BA Near Everything!
Apartment in Chicago
4.93 out of 5 average rating, 54 reviewsStunning Basement Apartment w/free street parking!
Apartment in Chicago
5.0 out of 5 average rating, 26 reviewsUrban Cottage
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- Rentals with a washer and dryer South Side
- Rentals with lake access South Side
- Condo rentals South Side
- Rentals with outdoor seating South Side
- Smoking-friendly rentals South Side
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- Waterfront rentals South Side
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- Pet-friendly rentals South Side
- Monthly Rentals South Side
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- Townhouse rentals South Side
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- Family-friendly rentals South Side
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- Rentals with an EV charger South Side
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