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Top South Side Luxury Hotels

The Wheeler Mansion
The Wheeler Mansion
10.0 out of 10, Exceptional, (1)
The price is CA $733
CA $886 total
includes taxes & fees
Aug 12 - Aug 13

Best Western Grant Park Hotel
Best Western Grant Park Hotel
8.2 out of 10, Very good, (2585)
The price is CA $168
CA $197 total
includes taxes & fees
Aug 24 - Aug 25

Hyatt Regency McCormick Place Chicago
Hyatt Regency McCormick Place Chicago
9.0 out of 10, Wonderful, (1009)
The price is CA $257
CA $334 total
includes taxes & fees
Aug 20 - Aug 21

Chinatown Hotel Chicago
Chinatown Hotel Chicago
5.4 out of 10, (1003)
The price is CA $109
CA $128 total
includes taxes & fees
Jul 27 - Jul 28
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

Hyatt Place Chicago-South/University Medical Center
10/10 Excellent
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South Side Hotels by Star Rating
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