A cityscape with a prominent building with a green dome, surrounded by greenery and a body of water.

Search Gay-Friendly Hotels in South Side

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check availability on South Side Gay-Friendly Hotels

Tonight
10 Aug - 11 Aug
Tomorrow
11 Aug - 12 Aug
This weekend
14 Aug - 16 Aug
Next weekend
21 Aug - 23 Aug

Our top choices for South Side LGBT-friendly hotels

1. Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
United States
Dawn
฿6,043
฿8,325 total
includes taxes & fees
7 Sept - 8 Sept
Sable at Navy Pier Chicago, Curio Collection by Hilton

2. Hilton Chicago

Hilton Chicago
Downtown Chicago
Canada
kun
฿5,592
฿7,619 total
includes taxes & fees
7 Sept - 8 Sept
Hilton Chicago

3. Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
United States
Kristie
฿4,680
฿6,544 total
includes taxes & fees
30 Aug - 31 Aug
Staypineapple, An Iconic Hotel, The Loop

4. SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown
Chinatown
United States
Brianna
฿5,326
฿6,332 total
includes taxes & fees
30 Aug - 31 Aug
SpringHill Suites by Marriott Chicago Chinatown

5. Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
West Lawn
United States
Ashley
฿3,637
฿4,600 total
includes taxes & fees
8 Sept - 9 Sept
Holiday Inn Chicago – Midway Airport S by IHG

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

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
Bedford Park
United States
Darryl
฿5,488
฿6,448 total
includes taxes & fees
18 Aug - 19 Aug
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

7. Chicago Marriott Midway

Chicago Marriott Midway
Bedford Park
United States
Dominique
฿5,620
฿6,603 total
includes taxes & fees
17 Aug - 18 Aug
Chicago Marriott Midway

8. Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
Downtown Chicago
United States
suzanne
฿5,733
฿7,799 total
includes taxes & fees
7 Sept - 8 Sept
Palmer House a Hilton Hotel

9. Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG
Downtown Chicago
United States
Chimere
฿4,761
฿6,057 total
includes taxes & fees
8 Sept - 9 Sept
Holiday Inn & Suites Chicago - Downtown by IHG

10. La Quinta Inn & Suites by Wyndham Chicago Downtown

La Quinta Inn & Suites by Wyndham Chicago Downtown
Downtown Chicago
United States
Paige
฿4,731
฿6,214 total
includes taxes & fees
8 Sept - 9 Sept
La Quinta Inn & Suites by Wyndham Chicago Downtown
View all properties

Top South Side Hotel Reviews

Explore a world of travel with Expedia