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

Gay friendly Hotels in South Side, Chicago

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Check availability on South Side Gay friendly Hotels

Tonight
Oct 16 - Oct 17
Tomorrow
Oct 17 - Oct 18
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

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 modern interior with a staircase, green upholstered seating, and artwork on the walls.
A breakfast bar with labeled sections for cereal and fruit, a blue oatmeal container, and a variety of condiments and utensils.
A hotel room with a blue sofa, a small table, a TV, a desk with a chair, and a large window.

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
P8,502
P9,989 total
includes taxes & fees
Nov 15 - Nov 16
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 modern lobby with a vending machine, a statue, and an exit sign.
A modern bar area with a curved counter, multiple stools, and pendant lighting. A menu board is visible on the wall, and a coffee machine is on the counter.

2. Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
West Lawn
United States
Paulina
P8,502
P10,611 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Chicago – Midway Airport S by IHG
Lobby lounge
A modern living room with two grey armchairs, a round coffee table, and a large potted plant.
A bar area with a black marble countertop, wicker bar stools, and a variety of bottles and glasses on shelves.
A hotel room with two beds, a desk, and a chair.

3. Chicago Marriott Midway

Chicago Marriott Midway
Bedford Park
United States
Carolyn
P10,719
P12,593 total
includes taxes & fees
Nov 15 - Nov 16
Chicago Marriott Midway
A modern living room with a sofa, two blue chairs, a round coffee table, and a unique ceiling design.
A modern lobby with a sofa, a coffee table, and a large digital art display.
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.

4. SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown
Chinatown
United States
Cayci
P11,860
P14,101 total
includes taxes & fees
Nov 1 - Nov 2
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 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.

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

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
United States
Shanequa
P11,952
P16,383 total
includes taxes & fees
Nov 12 - Nov 13
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 lobby with a reception desk, seating area, and a large window providing a view of the outdoors.
A modern outdoor patio with tables and chairs, a glass railing, and a view of a high-rise building.
A modern hotel entrance with glass doors, a visible reception desk, and signage for Hilton Garden Inn and Homewood Suites.

6. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
United States
Aran
P7,986
P9,494 total
includes taxes & fees
Nov 9 - Nov 10
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
P9,058
P10,769 total
includes taxes & fees
Nov 10 - Nov 11
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 hotel room with two beds, a desk with a television, a chair, a desk lamp, and a painting on the wall.
A restaurant interior with wooden tables and chairs, a carpeted floor, and framed pictures on the walls.
A marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.

8. Hilton Chicago

Hilton Chicago
Downtown Chicago
Canada
Anna
P10,665
P14,531 total
includes taxes & fees
Nov 13 - Nov 14
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 with a corner location, large windows, and a green awning.

9. Hampton Inn & Suites Chicago Downtown

Hampton Inn & Suites Chicago Downtown
Downtown Chicago
United States
Catherine
P8,479
P10,081 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn & Suites Chicago Downtown
A Holiday Inn & Suites building with multiple parking spaces and a modern architectural design.
A hotel room with a bed, desk, chair, two small tables, a sofa, and a large window with a city view.
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 spacious lobby with two elevators, a reception area, and a seating area with blue and white ottomans.

10. Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG
Downtown Chicago
United States
Donna
P9,584
P12,151 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Inn & Suites Chicago - Downtown by IHG
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Top South Side Hotel Reviews

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