
Condo holiday rentals in South Side
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Top-rated condo rentals in South Side
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for South Side condo rentals
Weekly condo rentals

Modern 2bd Near Med Dist & WLoop

1st Floor Condo Apartment Close to Midway Airport

Condo off the lake

Cozy 3 Bedroom Condo near University of Chicago

Modern Apt Near U of Chicago!

Luxury Penthouse w/ HOT TUB & Amazing Roof Deck

Charming Retreat with Modern Comforts / Spa Bath

Lux amazing Stay on University of Chicago Campus
Pet-friendly condo rentals

❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D

Lovely top floor 2BR/2BA, steps from everything!

Entire 3Bed/2Bath Condo Near McCormick & Metro

Picture Perfect 3Bed Steps from Train and FLW

Lincoln Square Gem!

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!

Cozy 1bdr Rogers Park, Loyola, Northwestern.

Modern Luxury In Old Town - Sleeps 4
Condo rentals with a pool

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

voco: Balcony & City View

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

Just remodeled apartment close to airport and mall

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

Iconic Style, Charming Lake View
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- South Bend Holiday rentals
- South Haven Holiday rentals
- Saugatuck Holiday rentals
- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- New Buffalo Holiday rentals
- Chicago Holiday rentals
- Rentals with a washing machine and dryer South Side
- Rentals with pools South Side
- Family-friendly rentals South Side
- Rentals with a fireplace South Side
- House rentals South Side
- Rentals with breakfast South Side
- Private suite rentals South Side
- Rentals with a patio South Side
- Rentals with an EV charger South Side
- Waterfront rentals South Side
- Pet-friendly rentals South Side
- Bed and breakfasts South Side
- Rentals with a fire pit South Side
- Rentals with outdoor seating South Side
- Fitness-friendly rentals South Side
- Smoking-friendly rentals South Side
- Rentals with lake access South Side
- Apartment rentals South Side
- Rentals with beach access South Side
- Rentals with a hot tub South Side
- Kid-friendly rentals South Side
- Townhouse rentals South Side
- Condo rentals Chicago
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- Oak Street Beach
- Humboldt Park
- Shedd Aquarium
- Frank Lloyd Wright Home and Studio
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Washington Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Illinois Beach State Park
- Garfield Park Conservatory
- Wicker Park
- Willis Tower
- Lincoln Park Zoo
- Raging Waves Waterpark
- The 606
- The Beverly Country Club