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 Chicago
4.82 out of 5 average rating, 146 reviewsThe Posh Apt. Mins to Downtown & Hyde Park
Apartment in Chicago
4.83 out of 5 average rating, 155 reviewsUniversity Retreat
Apartment in Chicago
4.96 out of 5 average rating, 266 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Apartment in Park Ridge
4.78 out of 5 average rating, 329 reviewsModern Garden apartment (WHOLE UNIT)
Apartment in Bridgeport
4.83 out of 5 average rating, 163 reviewsChicago Vintage Home
Apartment in Portage Park
4.96 out of 5 average rating, 114 reviewsComfortable, modern apartment 20 Min from Downtown
Apartment in Chicago
4.93 out of 5 average rating, 114 reviewsLuxurious - 10 Minutes to Downtown Chicago - Cozy
Apartment in Oak Park
4.86 out of 5 average rating, 251 reviewsCosmopolitan Nest in Oak Park North Side
Private apartment rentals
Apartment in Forest Park
4.88 out of 5 average rating, 102 reviewsHome in Forest Park upstairs.
Apartment in South Lawndale
4.87 out of 5 average rating, 190 reviews2 bedroom apartment near train line and bus lines!
Apartment in Forest Park
5.0 out of 5 average rating, 229 reviewsLike a Treehouse!
Apartment in Chicago
4.95 out of 5 average rating, 365 reviewsA Vintage Pink House in the Heart of Chicago
Apartment in Humboldt Park
4.98 out of 5 average rating, 111 reviewsHumboldt Park Loft
Apartment in Chicago
4.89 out of 5 average rating, 479 reviewsiKlektik House Chicago / Robin
Apartment in Blue Island
4.93 out of 5 average rating, 266 reviewsCharming Unique 2 Bdrm Apartment in Victorian Home
Apartment in Chicago
4.97 out of 5 average rating, 30 reviewsTravel To Chicago New City
Apartment rentals with a hot tub
Apartment in Chicago
4.87 out of 5 average rating, 163 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Apartment in West Town
4.88 out of 5 average rating, 398 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Apartment in Berwyn
4.91 out of 5 average rating, 208 reviews“Dream slice of urban homesteading.”
Apartment in Chicago
4.87 out of 5 average rating, 107 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Apartment in Logan Square
4.92 out of 5 average rating, 37 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Apartment in Chicago
4.8 out of 5 average rating, 10 reviewsThe Areal Oasis
Apartment in Chicago
5.0 out of 5 average rating, 11 reviewsLake, City, & River View Condo
Apartment in Chicago
4.87 out of 5 average rating, 45 reviewsSpectacular Rooftop Getaway in Heart of City
Destinations to explore
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- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes