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

Gay friendly Hotels in South Side

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Check availability on South Side Gay friendly Hotels

Tonight
30 Aug - 31 Aug
Tomorrow
31 Aug - 1 Sept
Next weekend
4 Sept - 6 Sept
In two weeks
11 Sept - 13 Sept

Our top choices for South Side LGBT-friendly hotels

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 kitchen with built-in appliances, wooden cabinets, and a variety of food items on shelves.
A modern restaurant with a bar area, multiple seating options, and a contemporary design.

1. SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown
Chinatown
United States
Ziyad
S$258
includes taxes & fees
7 Sept - 8 Sept
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 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.
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
Diane
S$203
includes taxes & fees
7 Sept - 8 Sept
Holiday Inn Chicago – Midway Airport S by IHG
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 hotel entrance with a glass door, a number 6500 sign above, and two signs indicating courtesy shuttle pick-up only.
A coffee station with two coffee machines, a coffee press, and various coffee pods and cups.

3. 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
S$262
includes taxes & fees
7 Sept - 8 Sept
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
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 Marriott hotel with a brick facade, a covered entrance, and landscaped areas with trees and shrubs.

4. Chicago Marriott Midway

Chicago Marriott Midway
Bedford Park
United States
Don
S$268
includes taxes & fees
8 Sept - 9 Sept
Chicago Marriott Midway
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.
A modern living room with a large window overlooking a body of water, a tripod, and a sofa.
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.

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

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
United States
Ashraf
S$300
includes taxes & fees
7 Sept - 8 Sept
Sable at Navy Pier Chicago, Curio Collection by Hilton
A large, multi-story hotel with a prominent entrance and classical architectural details.
A spacious hotel lobby with a long reception desk, multiple seating areas, and a large fireplace.
A spacious hotel lobby with a large seating area, a flat-screen TV, and a view of the ocean.
A grand ballroom with ornate chandeliers, a multi-tiered wedding cake centerpiece, and elegant floral arrangements on tables.

6. Hilton Chicago

Hilton Chicago
Downtown Chicago
United States
Konner
S$294
includes taxes & fees
7 Sept - 8 Sept
Hilton Chicago
A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.
A conference room with a long table, chairs, and a vase.
A hotel entrance with a sign for the Club Quarters Hotel, number 75, and a River Hotel sign.
A hotel room with a grey sofa, a bed with a white mattress, a wooden dresser, and a large window with curtains.

7. River Hotel

River Hotel
Downtown Chicago
United States
Meri
S$208
includes taxes & fees
31 Aug - 1 Sept
River Hotel
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 hot tub with a metal ladder, surrounded by white tiled walls and floor, with a large window providing a view of the cityscape.

8. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
United States
Dhannetta
S$230
includes taxes & fees
7 Sept - 8 Sept
Hilton Garden Inn Chicago Downtown South Loop
A spacious lobby with a checkered floor, a large sofa, and multiple chairs.
A hotel room with two beds, a desk with a computer, a chair, a TV, and a large mirror.
A modern room with a checkered floor, two round tables, two armchairs, and a large window with a view of the outside.
A modern kitchen with a built-in refrigerator, a coffee maker, and a flat-screen TV on the countertop.

9. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
Downtown Chicago
United States
Karaline
S$186
includes taxes & fees
7 Sept - 8 Sept
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.
A modern bar area with high stools, a bar counter, and shelves of liquor bottles.
A modern hotel room with a large window offering a view of the sea and a cityscape. There is a seating area with a sofa and a small table.
A rooftop terrace with a view of a beach and a Ferris wheel, featuring lounge chairs and a colorful mural.

10. The Wade

The Wade
Downtown Chicago
Canada
Ayomikun Jedidiah
S$226
includes taxes & fees
31 Aug - 1 Sept
The Wade
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Top South Side Hotel Reviews

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