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South Side Hotel Guide - Hotels with Connecting Rooms in South Side, Chicago

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Check availability on South Side Hotels with Connecting Rooms

Tonight
3 Dec - 4 Dec
Tomorrow
4 Dec - 5 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top South Side Hotels with Connecting Rooms

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, (1014)
"Great stay"
United States
Nikhil
The price is €128
includes taxes & fees
7 Dec - 8 Dec
Hyatt Place Chicago-South/University Medical Center
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, (1209)
"Will definitely stay there again ."
United States
Jose Remedios
The price is €124
includes taxes & fees
8 Dec - 9 Dec
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
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
The price is €119
includes taxes & fees
21 Dec - 22 Dec
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
The price is €146
includes taxes & fees
14 Dec - 15 Dec
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
The price is €231
includes taxes & fees
10 Dec - 11 Dec
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
The price is €99
includes taxes & fees
2 Jan - 3 Jan 2026
Swissotel - Chicago
Ballroom
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (2125)
"Loved and enjoyed our stay"
United States
Luis
The price is €125
includes taxes & fees
28 Dec - 29 Dec
Palmer House a Hilton Hotel
Lobby
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2095)
"Lovely hotel in a great spot!"
United States
Natasha
Silversmith Hotel Chicago Downtown
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, (2268)
"Perfect environment and location"
China
YIWEI
The price is €126
includes taxes & fees
16 Dec - 17 Dec
Sable at Navy Pier Chicago, Curio Collection by Hilton
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
The price is €87
includes taxes & fees
7 Dec - 8 Dec
Aloft Chicago Mag Mile
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 4 days ago
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

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