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Check availability on Sleepy Hollow Gay-Friendly Hotels

Our top choices for Sleepy Hollow LGBT-friendly hotels

Cocktail bar
Freehand Chicago

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very good, (2640)
"The room was spotless and the staff where great!"
United States
Maria
The price is ₹5,290
₹7,802 total
includes taxes & fees
4 Jan - 5 Jan 2026
Freehand 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, (2961)
"Great location and great staff!!"
United States
lynne
The price is ₹7,143
₹8,385 total
includes taxes & fees
14 Jan - 15 Jan 2026
Aloft Chicago Mag Mile
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, (2744)
"Clean room and friendly staff, overall good stay "
United States
eesaa saalik
The price is ₹7,017
₹10,891 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, (2261)
"This place was amazing !"
United States
Jayla Danyell
The price is ₹8,304
₹12,827 total
includes taxes & fees
23 Dec - 24 Dec
Sable at Navy Pier Chicago, Curio Collection by Hilton
Reception
River Hotel

River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (4854)
"Great location, comfortable room, and nice staff."
United States
Claudia
The price is ₹6,604
₹7,753 total
includes taxes & fees
28 Dec - 29 Dec
River Hotel
Ballroom
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, (3483)
"Great place to stay "
United States
RaShawna
The price is ₹7,340
₹8,617 total
includes taxes & fees
5 Jan - 6 Jan 2026
Hilton Chicago/Magnificent Mile Suites
2 bars/lounges
Hyatt Regency Chicago

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3394)
"I always love staying at this place when I visit"
Canada
William
The price is ₹12,297
₹17,090 total
includes taxes & fees
28 Dec - 29 Dec
Hyatt Regency Chicago
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, (3795)
"Comfortable Room, great location and Excellent Staff. "
United States
Charles
The price is ₹6,922
₹8,125 total
includes taxes & fees
15 Dec - 16 Dec
The Whitehall Hotel, BW Premier Collection
Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3153)
"Amazing stay very clean and beautiful views "
United States
Deigo
The price is ₹8,463
₹9,935 total
includes taxes & fees
13 Jan - 14 Jan 2026
Eurostars Magnificent Mile
Exterior
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, (2292)
"Great stay"
United States
Jeremy
The price is ₹9,404
₹13,933 total
includes taxes & fees
12 Jan - 13 Jan 2026
The Allegro Royal Sonesta Hotel Chicago 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

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