
Condo vacation rentals in South Side
Find and book unique condos on Airbnb
Top-rated condo rentals in South Side
Guests agree: these condos are highly rated for location, cleanliness, and more.
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

Beautiful Condo in North Kenwood with Parking

Modern Design 2bd Garden Condo Near United Center

The ModernFarmhouse Chicago-Near Downtown Chicago

Luxury Chicago 2BR | Spa Bath | Kitchen | Free Prk

Modern Apt Near U of Chicago!

FreeParking/Laundry/BigSpace!/FamilyFun!/GameRoom!

The Greenhouse - Chic 2BR Flat Near Fulton Market

Chic Chicago Spa Retreat – Luxe & Light-Filled
Pet-friendly condo rentals

Entire 3Bed/2Bath Condo Near McCormick & Metro

Spacious 3BR • Great for Groups • Fast WiFi • Pets

RockStar Pad W3A BoysTown/Wrigley Field/Parking

Convenient & Spacious 3BR Condo w/Free Parking

Picture Perfect 3Bed Steps from Train and FLW

The Urban Oasis | Outdoor Lounge • Sleeps 10+

NEW luxury Old Town 1-Bedroom condo

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!
Condo rentals with a pool

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

"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

Upscale, Smoke and Pet Free, Washer Dryer, Balcony
Destinations to explore
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Wicker Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Illinois Beach State Park
- Washington Park Zoo
- Museum of Science and Industry
- Brookfield Zoo
- Willis Tower
- Raging Waves Waterpark
- The Beverly Country Club
- The 606