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
  • Be picky

    Search almost a million properties worldwide

Check availability on South Side Gay-Friendly Hotels

Next weekend
In two weeks

Our top choices for South Side LGBT-friendly hotels

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
2.5 star property
West Lawn
8.2 out of 10, Very good, (1,004 reviews)
"Great staff , enjoyed our stay , very close to where we needed to be "
United States
Wafa
The price is ฿2,928
฿3,767 total
includes taxes & fees
5 Apr - 6 Apr
Holiday Inn Chicago – Midway Airport S by IHG

Chicago Marriott Midway

Chicago Marriott Midway
3.5 star property
Bedford Park
8.4 out of 10, Very good, (930 reviews)
"Great for an early morning flight from Midway on a layover with an airport shuttle. We had a great night sleep. "
United States
Paul
The price is ฿4,234
฿4,975 total
includes taxes & fees
3 Apr - 4 Apr
Chicago Marriott Midway

SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown
3.5 star property
Chinatown
9.6 out of 10, Exceptional, (1,003 reviews)
"Clean room, friendly staff"
United States
Shan
The price is ฿4,902
฿5,755 total
includes taxes & fees
5 Apr - 6 Apr
SpringHill Suites by Marriott Chicago Chinatown

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, (2,417 reviews)
"Great stay! I will stay here again on my next trip back this summer!"
United States
Letisha
The price is ฿5,462
฿7,532 total
includes taxes & fees
31 Mar - 1 Apr
Sable at Navy Pier Chicago, Curio Collection by Hilton

Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,709 reviews)
"We love staying here "
United States
Carrie
The price is ฿5,231
฿7,107 total
includes taxes & fees
1 Apr - 2 Apr
Hilton Chicago

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,228 reviews)
"Excellent stay."
United States
Fenton
The price is ฿6,485
฿8,772 total
includes taxes & fees
1 Apr - 2 Apr
Swissotel - Chicago

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,158 reviews)
"Nice location and good hotel"
United States
Taneshia
The price is ฿3,586
฿4,210 total
includes taxes & fees
5 Apr - 6 Apr
Aloft Chicago Mag Mile

River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (5,034 reviews)
"very beautiful hotel and great location "
United States
Ciandra
The price is ฿3,887
฿4,563 total
includes taxes & fees
13 Apr - 14 Apr
River Hotel

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1,758 reviews)
"Staff was friendly, explained the hotel and amenities well. Great location."
United States
Mary
The price is ฿5,560
฿6,528 total
includes taxes & fees
27 Apr - 28 Apr
The Wade

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,936 reviews)
"Hotel was really nice"
United States
LaCarr
The price is ฿4,064
฿4,771 total
includes taxes & fees
5 Apr - 6 Apr
Hilton Garden Inn Chicago Downtown South Loop
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