Schiller Woods view in Chicago of Illinois

Gay friendly Hotels in Westchester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Westchester Gay friendly Hotels

This weekend
26 Jun - 28 Jun
Next weekend
3 Jul - 5 Jul

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
3.0 star property
Westchester
8.6 out of 10, Excellent, (1,002 reviews)
"Clean room and good location would definitely stay here again"
United States
Jonas
The price is S$143
includes taxes & fees
5 Jul - 6 Jul
Four Points by Sheraton Chicago Westchester/Oak Brook
Terrace/patio

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, (2,550 reviews)
"The location was very convenient"
United States
Jeffrey
The price is S$350
includes taxes & fees
1 Jul - 2 Jul
Sable at Navy Pier Chicago, Curio Collection by Hilton
Reception

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,494 reviews)
"Beautiful place to stay."
United States
Charles Otto
The price is S$346
includes taxes & fees
6 Jul - 7 Jul
Palmer House a Hilton Hotel
Rooftop bar, al fresco dining, open daily

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,278 reviews)
"Would definitely stay there again"
United States
Benjy
The price is S$229
includes taxes & fees
1 Jul - 2 Jul
The Godfrey Hotel Chicago
Lobby

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,263 reviews)
"Wonderful stay"
United States
Taylor
The price is S$227
includes taxes & fees
5 Jul - 6 Jul
Silversmith Hotel Chicago Downtown
Interior detail

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,108 reviews)
"Good location, friendly staff"
United Kingdom
Philip
The price is S$282
includes taxes & fees
1 Jul - 2 Jul
Staypineapple, An Iconic Hotel, The Loop
2 bars/lounges

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,450 reviews)
"Staff was great."
United States
Marianne
The price is S$376
includes taxes & fees
9 Jul - 10 Jul
Hyatt Regency Chicago
Cocktail bar

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very good, (3,112 reviews)
"It was good place to stay for the Go Fest Event"
United States
Ken
The price is S$197
includes taxes & fees
8 Jul - 9 Jul
Freehand Chicago
Premium bedding, in-room safe, desk, blackout curtains

Hotel 55 Chicago Downtown

Hotel 55 Chicago Downtown
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,578 reviews)
"Great stay"
United States
Matt
The price is S$255
includes taxes & fees
5 Jul - 6 Jul
Hotel 55 Chicago Downtown
Reception hall

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,669 reviews)
The price is S$246
includes taxes & fees
30 Jun - 1 Jul
Eurostars Magnificent Mile
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.
View all properties

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 Soldier Field. While you're here, capture some great memories of your trip with stops at Navy Pier and United Center.
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.

Explore a world of travel with Expedia