Apartment vacation rentals in South Side
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Top-rated apartment rentals in South Side
Guests agree: these apartments are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for South Side apartment rentals
Weekly apartment rentals
Apartment in Avondale
4.97 out of 5 average rating, 120 reviewsDesigner Avondale Attic
Apartment in Bridgeport
4.83 out of 5 average rating, 162 reviewsChicago Vintage Home
Apartment in Chicago
4.87 out of 5 average rating, 189 reviews2 bedroom apartment near train line and bus lines!
Apartment in Chicago
4.98 out of 5 average rating, 110 reviewsHumboldt Park Loft
Apartment in West Town
4.92 out of 5 average rating, 309 reviewsSpacious & private! Free parking! Great location!
Apartment in McKinley Park
4.84 out of 5 average rating, 261 reviewsCharming loft style suite
Apartment in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Apartment in Chicago
4.83 out of 5 average rating, 567 reviewsGreat Location! Gold Coast! 07
Private apartment rentals
Apartment in Chicago
4.85 out of 5 average rating, 275 reviewsHUGE|3br/2ba/Near DT/Free Parking/WI-FI/Pilsen
Apartment in Lincoln Park
4.79 out of 5 average rating, 175 reviewsPerfect 1br In Lincoln Park - Steps to Depaul!
Apartment in Lincoln Park
4.98 out of 5 average rating, 304 reviewsRedesigned Lower Level Studio in Historic Building
Apartment in Forest Park
5.0 out of 5 average rating, 228 reviewsLike a Treehouse!
Apartment in Forest Park
4.93 out of 5 average rating, 593 reviewsPeaceful oasis in Forest Park
Apartment in Chicago
5.0 out of 5 average rating, 29 reviewsTravel To Chicago New City
Apartment in Chicago
4.97 out of 5 average rating, 65 reviewsLocation! Location! Location!
Apartment in Chicago
5.0 out of 5 average rating, 25 reviewsUrban Cottage
Apartment rentals with a hot tub
Apartment in Chicago
4.87 out of 5 average rating, 160 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Apartment in Berwyn
4.91 out of 5 average rating, 206 reviews“Dream slice of urban homesteading.”
Apartment in West Town
4.88 out of 5 average rating, 398 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Apartment in West Loop
4.87 out of 5 average rating, 106 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Apartment in Chicago
4.92 out of 5 average rating, 36 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Apartment in The Loop
4.8 out of 5 average rating, 10 reviewsThe Areal Oasis
Apartment in Chicago
4.87 out of 5 average rating, 45 reviewsSpectacular Rooftop Getaway in Heart of City
Apartment in Chicago
5.0 out of 5 average rating, 11 reviewsLake, City, & River View Condo
Destinations to explore
- Downtown Chicago Vacation rentals
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- Rentals with outdoor seating South Side
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- Condo rentals South Side
- Private suite rentals South Side
- Rentals with an EV charger South Side
- Rentals with pools South Side
- Pet-friendly rentals South Side
- Rentals with breakfast South Side
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- Rentals with a hot tub South Side
- Monthly Rentals South Side
- House rentals South Side
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- Smoking-friendly rentals South Side
- Townhouse rentals South Side
- Rentals with beach access South Side
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- Rentals with a patio South Side
- Apartment rentals Milwaukee
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