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Gay friendly Hotels in Sleepy Hollow

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Check availability on Sleepy Hollow Gay friendly Hotels

Our top choices for Sleepy Hollow LGBT-friendly hotels

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, (2,549 reviews)
"Great views of the lake, staff very helpful the rooms were clean and comfortable. Would stay there again!"
United States
Deborah
The price is S$371
includes taxes & fees
30 Jun - 1 Jul
Sable at Navy Pier Chicago, Curio Collection by Hilton
2 bars/lounges, rooftop bar

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,023 reviews)
"Great hotel to stay."
United States
Josias
The price is S$330
includes taxes & fees
30 Jun - 1 Jul
theWit Chicago, a Hilton Hotel
Indoor wedding

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,386 reviews)
"Nice Hotel, rooms are clean , the best for us was the location, i would recommend"
United States
Sergio
The price is S$314
includes taxes & fees
1 Jul - 2 Jul
Swissotel - Chicago
2 bars/lounges

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,514 reviews)
"Staff was great."
United States
Marianne
The price is S$344
includes taxes & fees
1 Jul - 2 Jul
Hyatt Regency Chicago
Room service – dining

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1,857 reviews)
"Excellent location, clean modern rooms."
United States
Molly
The price is S$324
includes taxes & fees
6 Jul - 7 Jul
The Wade
2 bars/lounges

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,667 reviews)
"Location was great"
United States
Pamela
The price is S$350
includes taxes & fees
2 Jul - 3 Jul
Sheraton Grand Chicago Riverwalk
Lobby

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,253 reviews)
"Awesome place"
United States
Mellany
The price is S$248
includes taxes & fees
7 Jul - 8 Jul
Silversmith Hotel Chicago Downtown
Reception hall

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,649 reviews)
"Had an amazing stay here!"
United States
Audrey
The price is S$242
includes taxes & fees
2 Jul - 3 Jul
Eurostars Magnificent Mile
View from property

The Blackstone, Autograph Collection

The Blackstone, Autograph Collection
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,010 reviews)
"Great location, clean hotel, and very accommodating staff."
United States
Neydee
The price is S$287
includes taxes & fees
1 Jul - 2 Jul
The Blackstone, Autograph Collection
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, (1,100 reviews)
"Good location, friendly staff"
United Kingdom
Philip
The price is S$250
includes taxes & fees
6 Jul - 7 Jul
Staypineapple, An Iconic Hotel, The 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 Sleepy Hollow Hotel Reviews

Frequently asked questions

Searching for gay-friendly accommodation in Sleepy Hollow?
If you're interested in booking a place that will welcome you to Sleepy Hollow, you can trust the hotels listed as LGBTQ-friendly on Expedia. Discover the people, places and traditions found only in Sleepy Hollow.
What is there to see in Sleepy Hollow?
During your trip, get out and enjoy everything Sleepy Hollow has to offer. You and your travelling companions may want to visit Wrigley Field, Soldier Field and Michigan Avenue. While you're here, capture some great memories of your trip with stops at Navy Pier and United Center.
What is an LGBTQ-friendly hotel in Sleepy Hollow?
LGBTQ-friendly hotels welcome all travellers who identify as LGBTQIA+. Expedia has worked with the International Gay and Lesbian Travel Association (IGLTA) to compile a selection of LGBTQ-friendly hotels worldwide. In Sleepy Hollow, hotels affiliated with IGLTA 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 Sleepy Hollow?
Stay at an LGBTQ-friendly hotel in Sleepy Hollow and you'll be around like-minded people, so you can relax and enjoy your trip. Some of Expedia's LGBTQ-friendly hotels go the extra mile and offer community-specific packages, exclusive tours and opportunities for social interaction.

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