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Check availability on Westchester Gay-Friendly Hotels

Our top choices for Westchester LGBT-friendly hotels

Bar (on property)
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, (1006)
"Thanks, great stay"
United States
Robert
The price is ₹8,434
₹9,444 total
includes taxes & fees
22 Dec - 23 Dec
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, (2649)
"The room was spotless and the staff where great!"
United States
Maria
The price is ₹5,308
₹7,829 total
includes taxes & fees
5 Jan - 6 Jan 2026
Freehand Chicago
Lobby
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2967)
"The room was very clean, the location was excellent."
United States
Craig
The price is ₹6,896
₹8,095 total
includes taxes & fees
24 Dec - 25 Dec
Aloft Chicago Mag Mile
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, (1991)
"A good place for stay "
United States
Julio
The price is ₹6,787
₹7,967 total
includes taxes & fees
29 Dec - 30 Dec
Club Quarters Hotel Wacker at Michigan, Chicago
Exterior
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (2750)
"Excellent place to stay "
United States
Teniesha
The price is ₹7,450
₹11,417 total
includes taxes & fees
11 Jan - 12 Jan 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
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, (2266)
"Great staff and restaurants!!"
United States
Abigale
The price is ₹8,407
₹12,959 total
includes taxes & fees
6 Jan - 7 Jan 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
View from room
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3498)
"Great place to stay "
United States
RaShawna
The price is ₹7,366
₹8,647 total
includes taxes & fees
5 Jan - 6 Jan 2026
Hilton Chicago/Magnificent Mile Suites
Lobby
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (2305)
"Great place to stay"
United States
Genevieve
The price is ₹8,801
₹13,235 total
includes taxes & fees
15 Jan - 16 Jan 2026
The Allegro Royal Sonesta Hotel Chicago Loop
Bar (on property)
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, (3802)
"Comfortable Room, great location and Excellent Staff. "
United States
Charles
The price is ₹6,945
₹8,153 total
includes taxes & fees
6 Jan - 7 Jan 2026
The Whitehall Hotel, BW Premier Collection
Pool
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1763)
"Great check in and responsive front desk staff. Housekeeping staff did a great job during our visit! "
United States
Steven
The price is ₹6,622
₹7,773 total
includes taxes & fees
6 Jan - 7 Jan 2026
Hilton Garden Inn Chicago Downtown South Loop
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

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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.