Gay friendly Hotels in Westchester

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Check availability on Westchester Gay friendly Hotels

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

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 S$145
includes taxes & fees
6 Jan - 7 Jan, 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 S$111
includes taxes & fees
4 Jan - 5 Jan, 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 S$111
includes taxes & fees
24 Jan - 25 Jan, 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 S$130
includes taxes & fees
22 Jan - 23 Jan, 2026
Aloft Chicago Mag Mile
Premium bedding, down duvets, pillow-top 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 S$140
includes taxes & fees
4 Jan - 5 Jan, 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 S$123
includes taxes & fees
11 Jan - 12 Jan, 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 S$135
includes taxes & fees
18 Jan - 19 Jan, 2026
Claridge House Chicago, Tapestry Collection by Hilton
Egyptian cotton sheets, premium bedding, pillow-top 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 S$115
includes taxes & fees
5 Jan - 6 Jan, 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 S$174
includes taxes & fees
20 Jan - 21 Jan, 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 S$155
includes taxes & fees
29 Jan - 30 Jan, 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

Looking for gay-friendly accommodation in Westchester?
Whether you are travelling with your partner or flying solo, you'll find gay-friendly hotels in Westchester on Expedia. People like Westchester for its shopping and restaurants.
What's the best LGBTQ-friendly accommodation in Westchester?
Four Points by Sheraton Chicago Westchester/Oak Brook is a top LGBTQ-friendly hotel, and features free Wi-Fi and pillowtop beds.
What should I do while I'm visiting Westchester?
During your trip, get out and enjoy everything Westchester has to offer. You and your travelling 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, also known as gay-friendly hotels, welcome all travellers who identify as LGBTQIA+. Expedia has compiled a selection of LGBTQ-friendly hotels worldwide. In Westchester, these hotels operate in a spirit of inclusiveness, prioritising a diverse environment in which guests are welcomed, respected and not obliged to declare or hide their sexual orientation.
What can I expect from LGBTQ-friendly accommodation in Westchester?
Take a holiday from the ordinary; stay at a gay-friendly hotel in Westchester, and you won't have to hide or your sexuality or your gender identity when you check in. Some of Expedia's LGBTQ-friendly hotels go the extra mile and offer wedding ceremonies and honeymoon packages for same-sex couples.

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