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 Bridgeport
4.83 out of 5 average rating, 163 reviewsChicago Vintage Home
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, 278 reviews*Entire City Apartment 1 block to Train Park Free
Apartment in Little Italy
4.98 out of 5 average rating, 202 reviewsSpacious 2BR on Quiet St - Free Park/Late Checkout
Apartment in West Town
4.96 out of 5 average rating, 266 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Apartment in Chicago
4.99 out of 5 average rating, 147 reviewsChicago Airbnb Newly Remodeled 2-Unit Apartment!
Apartment in Portage Park
4.95 out of 5 average rating, 115 reviewsComfortable, modern apartment 20 Min from Downtown
Apartment in Oak Park
4.97 out of 5 average rating, 168 reviewsChic Retreat in Historic Victorian House-Park Free
Private apartment rentals
Apartment in Chicago
4.97 out of 5 average rating, 30 reviewsTravel To Chicago New City
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, 28 reviewsUrban Cottage
Apartment in South Lawndale
5.0 out of 5 average rating, 17 reviewsFlor de Luna ~ Little Village Chicago Retreat
Apartment in East Side
4.85 out of 5 average rating, 67 reviewsLovely 1-BR Apt with full kitchen & living room
Apartment in Beverly
4.87 out of 5 average rating, 15 reviewsBeverly Cottage Loft
Apartment in Bridgeport
4.89 out of 5 average rating, 37 reviewsYour Perfect Spot :)-With Memory Foam Mattress!
Apartment in Chicago
4.97 out of 5 average rating, 67 reviewsLocation! Location! Location!
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, 402 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 West Loop
4.87 out of 5 average rating, 107 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Apartment in Chicago
4.92 out of 5 average rating, 37 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
5.0 out of 5 average rating, 12 reviewsLake, City, & River View Condo
Apartment in Chicago
4.87 out of 5 average rating, 45 reviewsSpectacular Rooftop Getaway in Heart of City
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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