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Find Hotels with Connecting Rooms in South Side, IL
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Top South Side Hotels with Connecting Rooms

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
Bedford Park
9.0 out of 10, Wonderful, (1210)
$116 nightly
The price is $136
Jan 2 - Jan 3, 2026
Total with taxes and fees

Hyatt Place Chicago-South/University Medical Center
Hyde Park
8.8 out of 10, Excellent, (1015)
$127 nightly
The price is $149
Dec 7 - Dec 8
Total with taxes and fees

SpringHill Suites by Marriott Chicago Chinatown
Chinatown
9.6 out of 10, Exceptional, (1008)
$112 nightly
The price is $131
Jan 1 - Jan 2, 2026
Total with taxes and fees

Chicago Marriott Midway
Bedford Park
8.4 out of 10, Very Good, (909)
$161 nightly
The price is $189
Dec 14 - Dec 15
Total with taxes and fees

Sophy Hyde Park
Hyde Park
9.6 out of 10, Exceptional, (1000)
$229 nightly
The price is $269
Dec 14 - Dec 15
Total with taxes and fees

Swissotel - Chicago
Downtown Chicago
9.0 out of 10, Wonderful, (2986)
$114 nightly
The price is $133
Jan 2 - Jan 3, 2026
Total with taxes and fees

Hilton Chicago/Magnificent Mile Suites
Downtown Chicago
9.0 out of 10, Wonderful, (3428)
$83 nightly
The price is $98
Dec 7 - Dec 8
Total with taxes and fees

Silversmith Hotel Chicago Downtown
Downtown Chicago
9.2 out of 10, Wonderful, (2096)
$127 nightly
The price is $149
Jan 4 - Jan 5, 2026
Total with taxes and fees
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.
Top South Side Hotel Reviews

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
10/10 Excellent
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