
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

Urban Oasis Getaway. 6 stops to downtown!

Beautiful Condo in North Kenwood with Parking

Cozy 2BR Apt | Easy Access from Midway

Quick Drive to Downtown Chicago & Early Check-In

Modern Design 2bd Garden Condo Near United Center

Entire Cozy Home in the Heart of Bronzeville

Penthouse w/ Massage Chair Near McCormick.

Lovely 4-bedroom condo with indoor fireplace
Pet-friendly condo rentals

816 PLZN Luxury Apt | Rooftop | Garage Parking

Entire 3Bed/2Bath Condo Near McCormick & Metro

RockStar Pad W3A BoysTown/Wrigley Field/Parking

Convenient & Spacious 3BR Condo w/Free Parking

Lincoln Square Gem!

Urban Oasis | Great for Families w/ Kids

Cozy 1bdr Rogers Park, Loyola, Northwestern.

Lincoln Park Hideaway - 5 Min Walk to the Park!
Condo rentals with a pool

Upscale, Washer Dryer, Smoke Free, Pet Free,

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

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

voco: Balcony & City View

30 E. Huron #2603 Private Residence

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
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Lincoln Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Illinois Beach State Park
- Willis Tower
- Wicker Park
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Moraine Hills State Park
- Chicago Cultural Center