Find Gay friendly Hotels in Westchester, IL

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Check availability on Westchester Gay friendly Hotels

Tonight
Dec 29 - Dec 30
Tomorrow
Dec 30 - Dec 31
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Westchester LGBT-friendly hotels

Breakfast and dinner served
Four Points by Sheraton Chicago Westchester/Oak Brook

Four Points by Sheraton Chicago Westchester/Oak Brook

Four Points by Sheraton Chicago Westchester/Oak Brook
3.0 star property
Westchester
8.6 out of 10, Excellent, (1010)
"Thanks, great stay"
United States
Robert
The price is ₩145,608
₩163,052 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Four Points by Sheraton Chicago Westchester/Oak Brook
Cocktail bar
Freehand Chicago

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very Good, (2665)
"It's an excellent place."
United States
Jose
The price is ₩84,337
₩124,390 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Freehand Chicago
Lobby sitting area
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2019)
"Great stay"
United States
Kramer
The price is ₩106,567
₩125,097 total
includes taxes & fees
Jan 24 - Jan 25, 2026
Club Quarters Hotel Wacker at Michigan, Chicago
Cocktail bar
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2996)
"Great place to stay"
United States
Elisha
The price is ₩123,983
₩145,543 total
includes taxes & fees
Jan 22 - Jan 23, 2026
Aloft Chicago Mag Mile
Premium bedding, down comforters, pillowtop beds, in-room safe
The Wade

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very Good, (1545)
"Great staff and great location. "
United States
Joe
The price is ₩134,074
₩157,390 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Wade
Breakfast, lunch and dinner served
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (3333)
"Great hotel "
United States
Anthony
The price is ₩117,553
₩137,994 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Club Quarters Hotel, Central Loop, Chicago
Cocktail bar
Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1495)
"Nice stay"
United States
Michelle
The price is ₩89,545
₩147,430 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Claridge House Chicago, Tapestry Collection by Hilton
Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Downtown Chicago
8.2 out of 10, Very Good, (3819)
"Hotel stay was excellent, great dining options walkable, easy parking "
United States
Jason
The price is ₩110,357
₩129,547 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Whitehall Hotel, BW Premier Collection
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton

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, (2285)
"Great staff and restaurants!!"
United States
Abigale
The price is ₩124,473
₩195,208 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Property amenity
citizenM Chicago Downtown

citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (4123)
"Great hotel"
United States
Richard
The price is ₩148,491
₩174,311 total
includes taxes & fees
Jan 29 - Jan 30, 2026
citizenM Chicago Downtown
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.
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Top Westchester Hotel Reviews

Frequently asked questions

Searching for an LGBTQ-friendly accommodation in Westchester?
Book a place where you can be yourself! You'll find LGBTQ-friendly hotels in Westchester on Expedia. People like Westchester for its shopping and restaurants.
What is the top LGBTQ-friendly accommodation in Westchester?
Four Points by Sheraton Chicago Westchester/Oak Brook is a top LGBTQ-friendly hotel, and features free WiFi and pillowtop beds.
What should I do while I'm visiting Westchester?
During your vacation, get out and explore all that Westchester has to offer. You and your traveling companions may want to visit Wrigley Field, Michigan Avenue, and United Center. While you're here, capture some great memories of your trip with stops at Soldier Field and Navy Pier.
What is a gay-friendly hotel in Westchester?
LGBTQ-friendly hotels are places where lesbian, gay, bisexual, and transgender travelers are proudly welcomed. Expedia has worked with the International Gay and Lesbian Travel Association (IGLTA) to compile a selection of LGBTQ-friendly hotels worldwide. In Westchester, hotels affiliated with IGLTA prioritize a diverse environment in which guests are welcomed, respected, and not obliged to declare or hide their sexual orientation.
What can I expect from an LGBTQ-friendly accommodation in Westchester?
Stay at an LGBTQ-friendly hotel in Westchester and you won't have to hide your same-sex relationship or your sexuality when you check-in. Some of Expedia's LGBTQ-friendly hotels go the extra mile and offer community-specific packages, exclusive tours, and opportunities for social interaction.