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Find Hotels with Connecting Rooms in South Side, IL

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Check availability on South Side Hotels with Connecting Rooms

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Dec 12 - Dec 14

Top South Side Hotels with Connecting Rooms

Free daily buffet breakfast
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

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

2.5 star property
Bedford Park
9.0 out of 10, Wonderful, (1210)
"Will definitely stay there again ."
United States
Jose Remedios
$116 nightly
The price is $136
Jan 2 - Jan 3, 2026
Total with taxes and fees
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
View from property
Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center

3.0 star property
Hyde Park
8.8 out of 10, Excellent, (1015)
"Great stay"
United States
Nikhil
$127 nightly
The price is $149
Dec 7 - Dec 8
Total with taxes and fees
Hyatt Place Chicago-South/University Medical Center
Lobby
SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown

3.5 star property
Chinatown
9.6 out of 10, Exceptional, (1008)
"Clean, good staff"
Canada
Veronique E
$112 nightly
The price is $131
Jan 1 - Jan 2, 2026
Total with taxes and fees
SpringHill Suites by Marriott Chicago Chinatown
Exterior
Chicago Marriott Midway

Chicago Marriott Midway

3.5 star property
Bedford Park
8.4 out of 10, Very Good, (909)
"The property was excellent the rooms fantastic and the staff were equally wonderful and helpful. "
United States
Leilani
$161 nightly
The price is $189
Dec 14 - Dec 15
Total with taxes and fees
Chicago Marriott Midway
View from room
Sophy Hyde Park

Sophy Hyde Park

4.0 star property
Hyde Park
9.6 out of 10, Exceptional, (1000)
"Room and location were great"
United States
Latasha
$229 nightly
The price is $269
Dec 14 - Dec 15
Total with taxes and fees
Sophy Hyde Park
Reception
Swissotel - Chicago

Swissotel - Chicago

4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (2986)
"Great stay"
Canada
Lorrington Ashford
$114 nightly
The price is $133
Jan 2 - Jan 3, 2026
Total with taxes and fees
Swissotel - Chicago
Ballroom
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3428)
"Great hotel located in nice area."
United States
Robert
$83 nightly
The price is $98
Dec 7 - Dec 8
Total with taxes and fees
Hilton Chicago/Magnificent Mile Suites
Lobby
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2096)
"Lovely hotel in a great spot!"
United States
Natasha
$127 nightly
The price is $149
Jan 4 - Jan 5, 2026
Total with taxes and fees
Silversmith Hotel Chicago Downtown
Cocktail bar
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2941)
"Great location and great staff!!"
United States
lynne
$90 nightly
The price is $106
Jan 1 - Jan 2, 2026
Total with taxes and fees
Aloft Chicago Mag Mile
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2269)
"Perfect environment and location"
China
YIWEI
$119 nightly
The price is $140
Dec 16 - Dec 17
Total with taxes and fees
Sable at Navy Pier Chicago, Curio Collection by Hilton
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

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

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

10/10 Excellent
"The need to stay in Chicago overnight was unplanned so finding the room clean and looking comfortable right away made my stress level come down"
Mary 1-night trip
Posted 5 days ago
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

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