South Side Vacation Rentals
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Our top choices for South Side vacation rentals
2MI to Obama Center - Pet-Friendly near UOC!
2MI to Obama Center - Pet-Friendly near UOC!Woodlawn
9.4 out of 10, Exceptional, (3 reviews)
"Great host very accommodating."
Kali P.
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10Brighton Park
10.0 out of 10, Exceptional, (2 reviews)
"The rooms were spotless. The apartment was spacious. I enjoyed my stay. "
Rachel
The price is ￥16,295
￥48,713 total
includes taxes & fees
Aug 4 - Aug 5
Comfortable 3BR Getaway w/ Bonus Attic Lounge to Relax
Comfortable 3BR Getaway w/ Bonus Attic Lounge to RelaxCalumet Park
9.2 out of 10, Wonderful, (9 reviews)
"Lakeia was very accommodating throughout our stay."
Timothy K.
The price is ￥19,893
￥43,891 total
includes taxes & fees
Aug 4 - Aug 5
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6Brighton Park
8.6 out of 10, Excellent, (21 reviews)
"Excellent location and go anywhere so close."
Yiu S.
The price is ￥14,682
￥41,268 total
includes taxes & fees
Aug 5 - Aug 6
Spacious 3BR · Bronzeville/South Loop · Sleeps 8
Spacious 3BR · Bronzeville/South Loop · Sleeps 8Near South Side
9.0 out of 10, Wonderful, (4 reviews)
"Excellent stay! The property was clean and an easy walk to McCormick Place convention center. The space was colossal and well appointed, with soap and towels provided for the shower. We were greeted by a wonderful gentleman who took the time to explain the Chicago area to us. Checkout was a breeze—just had to leave our keys—and the instructions were very clear. There was only minimal housekeeping required before leaving the apartment. I would definitely stay here again"
Ilir T.
The price is ￥35,172
￥89,195 total
includes taxes & fees
Jul 9 - Jul 10
The price is ￥39,253
￥56,259 total
includes taxes & fees
Jul 7 - Jul 8
9.2 out of 10, Wonderful, (1,205 reviews)
"Great location"
JAVIER
The price is ￥27,291
￥36,771 total
includes taxes & fees
Jul 8 - Jul 9
ENVITAE Hotel, 4BR Luxury Modern Apartments
ENVITAE Hotel, 4BR Luxury Modern ApartmentsNear North Side
9.6 out of 10, Exceptional, (15 reviews)
"The property was clean and the location was great."
Steven C.
The price is ￥31,945
￥85,013 total
includes taxes & fees
Jul 8 - Jul 9
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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Top South Side Hotel Reviews
Jaslin Hotel
10/10 Excellent
Find out more about South Side
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