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
4.93 out of 5 average rating, 115 reviewsLuxurious - 10 Minutes to Downtown Chicago - Cozy
Apartment in Chicago
4.99 out of 5 average rating, 149 reviewsChicago Airbnb Newly Remodeled 2-Unit Apartment!
Apartment in Chicago
4.95 out of 5 average rating, 368 reviewsA Vintage Pink House in the Heart of Chicago
Apartment in Oak Park
4.89 out of 5 average rating, 347 reviewsCharming Chicago-Style, Vintage, Tv NFL PASS
Apartment in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Apartment in Chicago
4.82 out of 5 average rating, 137 reviewsPerfect Private Getaway in Perfect Pilsen
Apartment in Berwyn
4.87 out of 5 average rating, 151 reviewsThe Green Bungalow: Charming 1-BR apt. with patio
Apartment in Bridgeport
4.83 out of 5 average rating, 163 reviewsChicago Vintage Home
Private apartment rentals
Apartment in Chicago
4.96 out of 5 average rating, 266 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Apartment in Chicago
4.96 out of 5 average rating, 246 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Apartment in Oak Park
4.97 out of 5 average rating, 169 reviewsChic Retreat in Historic Victorian House-Park Free
Apartment in Humboldt Park
4.98 out of 5 average rating, 111 reviewsHumboldt Park Loft
Apartment in Chicago
4.94 out of 5 average rating, 271 reviewsLovely City Apartment-Near Downtown-Food-Train
Apartment in Chicago
4.99 out of 5 average rating, 107 reviewsNewly Renovated, Spacious 2BR in Andersonville
Apartment in Chicago
5.0 out of 5 average rating, 17 reviewsHistoric Charm Near Shops &Parks and UChicago
Apartment in Chicago
4.95 out of 5 average rating, 22 reviewsNEW Garden Unit Close to Downtown
Apartment rentals with a hot tub
Apartment in Chicago
4.87 out of 5 average rating, 165 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Apartment in West Town
4.88 out of 5 average rating, 402 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Apartment in Berwyn
4.91 out of 5 average rating, 209 reviews“Dream slice of urban homesteading.”
Apartment in Logan Square
4.92 out of 5 average rating, 38 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Apartment in Chicago
5.0 out of 5 average rating, 12 reviewsLake, City, & River View Condo
Apartment in Chicago
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
New place to stayCloud9 | Co-Working+Golf|@Fulton Market |The Boho
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- Rentals with a washer and dryer South Side
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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