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Search Gay-Friendly Hotels in South Side

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Check availability on South Side Gay-Friendly Hotels

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 Gay-Friendly Hotels

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 ฿2,337
฿3,684 total
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 ฿3,518
฿4,930 total
includes taxes & fees
14 Dec - 15 Dec
Palmer House a Hilton Hotel
Exterior
Hilton Chicago

Hilton Chicago

4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (2334)
"We had a great stay and will be back again."
United States
Amber
The price is ฿3,387
฿4,915 total
includes taxes & fees
20 Dec - 21 Dec
Hilton Chicago
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 ฿3,944
฿4,634 total
includes taxes & fees
9 Dec - 10 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 ฿3,783
฿4,441 total
includes taxes & fees
22 Dec - 23 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 ฿4,639
฿5,450 total
includes taxes & fees
14 Dec - 15 Dec
Chicago Marriott Midway
Ballroom
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3426)
"Great stay!"
United States
Rose
The price is ฿2,667
฿3,131 total
includes taxes & fees
7 Dec - 8 Dec
Hilton Chicago/Magnificent Mile Suites
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 ฿3,019
฿4,635 total
includes taxes & fees
23 Dec - 24 Dec
Sable at Navy Pier Chicago, Curio Collection by Hilton
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
The price is ฿2,106
฿3,450 total
includes taxes & fees
1 Jan - 2 Jan 2026
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
The price is ฿2,753
฿3,232 total
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

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