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

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Check availability on South Side Gay-Friendly Hotels

Tonight
3 Oct - 4 Oct
Tomorrow
4 Oct - 5 Oct
Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct

Our top choices for South Side LGBT-friendly hotels

A hotel room with a bed, a desk, a chair, a TV, and a colorful rug.
A coffee station with two espresso machines, a coffee grinder, and various coffee-related items.
A hotel room with a blue sofa, a small table, a TV, a desk with a chair, and a large window.
A hotel reception desk with a modern design, including a digital display and a sign indicating it is a non-smoking property.

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

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
Bedford Park
United States
Roberto
Rp2.771.710
Rp3.256.205 total
includes taxes & fees
31 Oct - 1 Nov
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
A modern living room with a sofa, two blue chairs, a round coffee table, and a unique ceiling design.
A modern kitchen with built-in appliances, wooden cabinets, and a variety of food items on shelves.
A modern hotel room with a bed, a sofa, a desk, and artwork on the walls.
A modern restaurant with a bar area, multiple seating options, and a contemporary design.

2. SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown
Chinatown
United States
Cayci
Rp3.041.728
Rp3.616.310 total
includes taxes & fees
1 Nov - 2 Nov
SpringHill Suites by Marriott Chicago Chinatown
A modern bar area with a bar counter, seating, and large windows offering a view of the street.
A hotel room with a bed, a seating area with a table and a plant, a window with a city view, and a radiator.
A modern lobby with a vending machine, a statue, and an exit sign.
A reception desk with a mosaic wall, a digital display, and a sign indicating amenities like restrooms and a meeting room.

3. Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
West Lawn
United States
Allen
Rp2.718.064
Rp3.369.556 total
includes taxes & fees
14 Oct - 15 Oct
Holiday Inn Chicago – Midway Airport S by IHG
Lobby
A hotel room with two beds, a desk, and a chair.
A bar area with a black marble countertop, wicker bar stools, and a variety of bottles and glasses on shelves.
A modern living room with two grey armchairs, a round coffee table, and a large potted plant.

4. Chicago Marriott Midway

Chicago Marriott Midway
Bedford Park
United States
Carolyn
Rp2.879.002
Rp3.382.252 total
includes taxes & fees
2 Nov - 3 Nov
Chicago Marriott Midway
A large, historic building with a central courtyard surrounded by trees.
A marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.
A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.
A restaurant interior with wooden tables and chairs, a carpeted floor, and framed pictures on the walls.

5. Hilton Chicago

Hilton Chicago
Downtown Chicago
United States
Alan
Rp2.977.865
Rp4.067.686 total
includes taxes & fees
30 Oct - 31 Oct
Hilton Chicago
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.
A view from a room with a large window overlooking a cityscape at night, featuring a river and illuminated buildings.
A spacious outdoor dining area with large windows overlooking the sea, featuring multiple tables and stools.
A modern living room with a large window overlooking a body of water, a tripod, and a sofa.

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

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
United States
Shanequa
Rp4.096.409
Rp5.486.792 total
includes taxes & fees
1 Nov - 2 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
A modern kitchen with a marble island, fruit bowls, and a city view.
A modern hotel room with a city view, a seating area with two sofas and a coffee table, and a dining area with a table and chairs.
A modern bar area with a central bar, seating, and a distinctive ceiling design.
A modern lounge area with a central bar, seating arrangements, and a decorative chandelier.

7. Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
Downtown Chicago
United States
Ruby
Rp3.024.740
Rp4.233.963 total
includes taxes & fees
31 Oct - 1 Nov
Fairmont Chicago at Millennium Park
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.
A modern hotel lobby with a reception desk, seating area, and a large window providing a view of the outdoors.
A hot tub with a metal ladder, surrounded by white tiled walls and floor, with a large window providing a view of the cityscape.
A modern outdoor patio with tables and chairs, a glass railing, and a view of a high-rise building.

8. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
United States
Aran
Rp3.389.533
Rp4.029.815 total
includes taxes & fees
25 Oct - 26 Oct
Hilton Garden Inn Chicago Downtown South Loop
A modern kitchen with a large window, a dining area, and a view of the sea.
A modern restaurant interior with a long counter, booths, and tables.
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.
A modern living room with a sectional sofa, a fireplace, and a large window offering a city view.

9. Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
Downtown Chicago
United States
Cecilia
Rp3.404.733
Rp4.047.885 total
includes taxes & fees
25 Oct - 26 Oct
Homewood Suites by Hilton Chicago Downtown South Loop
A dining table set for six with a cityscape view through large windows.
A modern hotel room with a large window offering a cityscape view, a green sofa, two armchairs, and a coffee table with flowers.
The exterior of the Swissotel building with its distinctive glass facade and the hotel's name displayed prominently.
A modern hotel room with a large window offering a city skyline view, a round table with four chairs, and a ceiling with recessed lighting.

10. Swissotel - Chicago

Swissotel - Chicago
Downtown Chicago
United States
Michael
Rp3.419.932
Rp4.695.761 total
includes taxes & fees
31 Oct - 1 Nov
Swissotel - Chicago
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Top South Side Hotel Reviews

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