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
16 Oct - 17 Oct
Tomorrow
17 Oct - 18 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 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 breakfast bar with labeled sections for cereal and fruit, a blue oatmeal container, and a variety of condiments and utensils.
A modern interior with a staircase, green upholstered seating, and artwork on the walls.
A coffee station with two espresso machines, a coffee grinder, and various coffee-related items.

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
₹12,819
₹15,060 total
includes taxes & fees
15 Nov - 16 Nov
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
A modern bar area with a bar counter, seating, and large windows offering a view of the street.
A reception desk with a mosaic wall, a digital display, and a sign indicating amenities like restrooms and a meeting room.
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.

2. Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
West Lawn
United States
Paulina
₹12,819
₹15,999 total
includes taxes & fees
8 Nov - 9 Nov
Holiday Inn Chicago – Midway Airport S by IHG
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.
Lobby lounge
A hotel room with two beds, a desk, and a chair.

3. Chicago Marriott Midway

Chicago Marriott Midway
Bedford Park
United States
Carolyn
₹16,159
₹18,984 total
includes taxes & fees
15 Nov - 16 Nov
Chicago Marriott Midway
A modern living room with a sofa, two blue chairs, a round coffee table, and a unique ceiling design.
A modern restaurant with a bar area, multiple seating options, and a contemporary 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.

4. SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown
Chinatown
United States
Cayci
₹17,862
₹21,236 total
includes taxes & fees
11 Nov - 12 Nov
SpringHill Suites by Marriott Chicago Chinatown
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.
A waterfront cityscape with modern buildings, a Ferris wheel, and several cruise ships docked.
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.

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

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
United States
Shanequa
₹17,918
₹24,577 total
includes taxes & fees
12 Nov - 13 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.
A modern hotel entrance with glass doors, a visible reception desk, and signage for Hilton Garden Inn and Homewood Suites.
A modern outdoor patio with tables and chairs, a glass railing, and a view of a high-rise building.
A modern hotel lobby with a reception desk, seating area, and a large window providing a view of the outdoors.

6. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
United States
Aran
₹11,623
₹13,818 total
includes taxes & fees
9 Nov - 10 Nov
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 bar area with a long counter, multiple bar stools, and a mix of seating options including a high table and chairs.
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.
A modern restaurant interior with a long counter, booths, and tables.

7. Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
Downtown Chicago
United States
Cynthia
₹13,655
₹16,234 total
includes taxes & fees
10 Nov - 11 Nov
Homewood Suites by Hilton Chicago Downtown South Loop
A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.
A marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.
A restaurant interior with wooden tables and chairs, a carpeted floor, and framed pictures on the walls.
A hotel room with two beds, a desk with a television, a chair, a desk lamp, and a painting on the wall.

8. Hilton Chicago

Hilton Chicago
Downtown Chicago
Canada
Anna
₹15,760
₹21,561 total
includes taxes & fees
30 Oct - 31 Oct
Hilton Chicago
A modern interior with a geometric light wall, a staircase, and hanging crystal chandeliers.
A modern restaurant with a long counter, bar stools, and high ceilings with exposed beams.
A modern lobby with a reception desk, seating area, staircase, and decorative lighting.
A modern hotel room with a kitchen area, a dining table with chairs, a sofa, and a large window with curtains.

9. Hampton Inn & Suites Chicago Downtown

Hampton Inn & Suites Chicago Downtown
Downtown Chicago
United States
Catherine
₹12,783
₹15,198 total
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn & Suites Chicago Downtown
A Holiday Inn & Suites building with multiple parking spaces and a modern architectural design.
A breakfast buffet with a variety of fruits, pastries, and beverages on a wooden table, set against a modern room with a white sofa and a wooden accent wall.
A hotel room with a bed, desk, chair, two small tables, a sofa, and a large window with a city view.
A modern lobby with a central seating area, a reception desk, and elevators.

10. Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG
Downtown Chicago
United States
Donna
₹14,068
₹17,866 total
includes taxes & fees
11 Nov - 12 Nov
Holiday Inn & Suites Chicago - Downtown by IHG
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Top South Side Hotel Reviews

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