
Holiday rentals in South Side
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Top-rated holiday rentals in South Side
Guests agree: these stays are highly rated for location, cleanliness and more.
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Popular amenities for South Side holiday rentals
Other great holiday rentals in South Side

Private room in Chicago
4.59 out of 5 average rating, 58 reviewsL12. Next to downtown
Guest favourite

Private room in Chicago
4.93 out of 5 average rating, 15 reviewsChicagoChinatownCenterB

Private room in Chicago
4.53 out of 5 average rating, 60 reviewsPrivate room in Bridgeport. C3

Private room in Chicago
4.66 out of 5 average rating, 35 reviewsPerfect Oasis 4mins walk to University & hospital
Guest favourite

Private room in Chicago
4.83 out of 5 average rating, 550 reviewsThe Blue Room

Private room in Chicago
4.57 out of 5 average rating, 258 reviewsFrida 2720 (2F)

Private room in Chicago
4.69 out of 5 average rating, 26 reviewsSouth Loop Luxury Lofts
Guest favourite

Private room in Chicago
4.9 out of 5 average rating, 10 reviewsConfortable and affordable
Destinations to explore
- Chicago Holiday rentals
- Indianapolis Holiday rentals
- Downtown Chicago Holiday rentals
- Platteville Holiday rentals
- St. Louis Holiday rentals
- Detroit Holiday rentals
- Columbus Holiday rentals
- Louisville Holiday rentals
- Southern Indiana Holiday rentals
- Cincinnati Holiday rentals
- Milwaukee Holiday rentals
- Wisconsin River Holiday rentals
- House rentals South Side
- Family-friendly rentals South Side
- Private suite rentals South Side
- Smoking-friendly rentals South Side
- Townhouse rentals South Side
- Rentals with outdoor seating South Side
- Flat rentals South Side
- Rentals with breakfast South Side
- Rentals with a firepit South Side
- Bed and breakfasts South Side
- Rentals with a washing machine and dryer South Side
- Rentals with lake access South Side
- Rentals with pools South Side
- Waterfront rentals South Side
- Rentals with an EV charger South Side
- Rentals with a fireplace South Side
- Fitness-friendly rentals South Side
- Rentals with a hot tub South Side
- Rentals with a patio South Side
- Pet-friendly rentals South Side
- Apartment rentals South Side
- Rentals with beach access South Side
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- 875 North Michigan Avenue
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Wicker Park
- Garfield Park Conservatory
- Illinois Beach State Park
- Lincoln Park Zoo
- Washington Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Willis Tower
- Raging Waves Waterpark
- The 606
- The Beverly Country Club