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Featured Condo Rentals in South Side

The Chic Urban Oasis Near the Lake!

7.6 out of 10, Good, (4)
"Everything about the host and stay was amazing this will be my go to spot for my family and me"
The Chic Urban Oasis Near the Lake!

Modern Duplex-Obama & University Chicago Area 3BR, 2.5Bath. Enjoy entire unit.

2.5 star property
Modern Duplex-Obama & University Chicago Area 3BR, 2.5Bath. Enjoy entire unit.

Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions

8.0 out of 10, Very good, (8)
"We enjoyed our stay, and the condo was perfect for my daughter and me. Great location, prompt responses to all communication with owner, super clean and very comfy beds! Main building corridor could use some sprucing up, but nothing major. Overall, very satisfied! Thanks, Khoy!"
Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions

Chic 2-bedroom Condo near McCormick Pl with Parking Spot

10.0 out of 10, Exceptional, (1)
"Perfect apartment to go to the convention center, our walk to the event was closer than our friends who stayed in the Marriott and walked via the bridges. "
Chic 2-bedroom Condo near McCormick Pl with Parking Spot

Bronzeville Manor walking distance to hospitals

10.0 out of 10, Exceptional, (15)
"Great location, very clean place. Ample street parking and the owner is very nice. I’ll definitely be booking this location again."
Bronzeville Manor walking distance to hospitals

Beautiful, modern 3 bed 2 bath condo near Hyde Park, Obama Center and Lakefront

10.0 out of 10, Exceptional, (2)
"Clean, comfortable, and quiet! We enjoyed the condo very much. "
Beautiful, modern 3 bed 2 bath condo near Hyde Park, Obama Center and Lakefront

1-bedroom condo next to Chicago Midway International Airport

10.0 out of 10, Exceptional, (5)
"super nice place!"
1-bedroom condo next to Chicago Midway International Airport

Modern Condo-Obama & University of Chicago Area

8.8 out of 10, Excellent, (11)
"Great place!"
Modern Condo-Obama & University of Chicago Area

Gorgeous N. Kenwood/Hyde Park

2.0 star property
9.6 out of 10, Exceptional, (5)
"Unit was very nice and spacious. Communication with owner throughout my stay was excellent. I will definitely consider this unit again my next trip to Chicago."
Gorgeous N. Kenwood/Hyde Park

4 #2S - 5 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown

9.6 out of 10, Exceptional, (12)
"Everything was as advertised and super convenient for our group if 8. Highly recommended VRBO! "
4 #2S - 5 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown

1 #12 - 2 Bedroom / 1 Bath Condo near McCormick Place, Wintrust Arena, Chinatown

9.6 out of 10, Exceptional, (12)
"This was a great place for us to stay while members of our family were at the convention. Cheaper than a hotel room, more privacy and more amenities. "
1 #12 - 2 Bedroom / 1 Bath Condo near McCormick Place, Wintrust Arena, Chinatown

4 #1N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown

9.0 out of 10, Wonderful, (11)
"We enjoyed the apartment. It was clean, had enough bath towels and soaps . The beds were comfortable and the bed linens were comfortable. Each bedroom having their own bathroom was a real bonus. the CTA stop was a fairly short walk. Their we re a lot of places to eat that were within walking distance., The kitchen needed more supplies such as dish towels, mixing bowl and spatula. Enjoyed the stay, would stay again if the need arises."
4 #1N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown

3 #3B - Modern 3 bedroom Condo - McCormick Place, Wintrust Arena, Chinatown

9.6 out of 10, Exceptional, (26)
"Good location and clean property."
3 #3B - Modern 3 bedroom Condo - McCormick Place, Wintrust Arena, Chinatown

Luxury Stay on UChicago Campus 11 min walk to hospitals

10.0 out of 10, Exceptional, (5)
"Our family stay was wonderful! The property was great, the owners were available and courteous. "
Luxury Stay on UChicago Campus 11 min walk to hospitals

3 #3A - 3 Bedroom Condo w Parking - Chinatown, McCormick Place, Wintrust Arena

9.6 out of 10, Exceptional, (24)
"Pics didn’t really line up with the place, but that’s okay. Area was pretty safe, easy to drive around. Hard to get ahold of owners at times, but besides that, it was a good time."
3 #3A - 3 Bedroom Condo w Parking - Chinatown, McCormick Place, Wintrust Arena

A luxury vintage condo close to lakefront and minutes from downtown!

A luxury vintage condo close to lakefront and minutes from downtown!

1 #33 - 4 Bedroom / 2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown

10.0 out of 10, Exceptional, (13)
"Our group of 16 people really enjoyed staying at this property. We were so close to everything, surrounded by great food amd shopping, we felt very safe, and the property manager was so responsive to us! We would recommended this property to any family or big group and will be staying here if we come back to Chicago!"
1 #33 - 4 Bedroom / 2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown

Spacious two bedroom condo with a cozy feel!

8.8 out of 10, Excellent, (6)
"Very nice amenities. Comfortable beds."
Spacious two bedroom condo with a cozy feel!

Tranquil 2-bedroom condo in charming Chicago with WiFi, AC

7.0 out of 10, Good, (4)
"We stayed for 4 days for the ACDC concert. It was a cute little place. People all around were friendly. A big suggestion when you arrive. Go to the side door not the front door. We had a very friendly maintenance man named Berto! Only a few issues to note. The pillows were terrible! Not alot around to walk to but there was a few grocery stores. "
Tranquil 2-bedroom condo in charming Chicago with WiFi, AC

Spacious 2 bedroom 2 bath 10 Minutes to Down Town

9.8 out of 10, Exceptional, (19)
"Awesome place"
Spacious 2 bedroom 2 bath 10 Minutes to Down Town
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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