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Check availability on Sleepy Hollow Gay-Friendly Hotels

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Our top choices for Sleepy Hollow LGBT-friendly hotels

A modern interior with a staircase, green upholstered seating, and artwork on the walls.

1. Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
2.5 star property
Bedford Park
9.0 out of 10, Wonderful, (1,376 reviews)
"Enjoyed my stay."
United States
Ambreauna
The price is ฿4,291
฿5,041 total
includes taxes & fees
28 Nov - 29 Nov
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
A modern bar area with a bar counter, seating, and large windows offering a view of the street.

2. Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
2.5 star property
West Lawn
8.2 out of 10, Very good, (1,000 reviews)
"Clean and comfortable rooms."
United States
Laura
The price is ฿3,749
฿4,739 total
includes taxes & fees
25 Nov - 26 Nov
Holiday Inn Chicago – Midway Airport S by IHG
A grand hotel facade with classical architecture, featuring tall columns, ornate detailing, and a prominent entrance with a marquee.

3. Hyatt House Chicago Medical/University District

Hyatt House Chicago Medical/University District
3.5 star property
Near West Side
9.2 out of 10, Wonderful, (1,624 reviews)
"We had a lovely stay!"
Netherlands
lieneke
The price is ฿3,717
฿4,419 total
includes taxes & fees
23 Nov - 24 Nov
Hyatt House Chicago Medical/University District
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

4. 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, (2,763 reviews)
"Best stay, wonderful property."
Canada
Bonnie
The price is ฿4,421
฿6,421 total
includes taxes & fees
23 Nov - 24 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

5. 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, (2,205 reviews)
"Great place to stay at"
United States
Aran
The price is ฿3,273
฿3,891 total
includes taxes & fees
23 Nov - 24 Nov
Hilton Garden Inn Chicago Downtown South Loop
A modern kitchen with a large window, a dining area, and a view of the sea.

6. Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,525 reviews)
"Wonderful room and great breakfast buffet!"
United States
Nicole
The price is ฿3,560
฿4,233 total
includes taxes & fees
23 Nov - 24 Nov
Homewood Suites by Hilton Chicago Downtown South Loop
The Claridge House building with a sign, American and another flag, and outdoor seating with umbrellas.

7. 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, (1,435 reviews)
"Convenient location near good restaurants."
United States
Scott
The price is ฿3,131
฿4,714 total
includes taxes & fees
22 Nov - 23 Nov
Claridge House Chicago, Tapestry Collection by Hilton
A multi-story hotel with a prominent sign reading "Crowne Plaza."

8. Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (2,759 reviews)
"Nice hotel and location was perfect."
United States
Chriselda
The price is ฿4,526
฿5,381 total
includes taxes & fees
25 Nov - 26 Nov
Crowne Plaza Chicago West Loop by IHG
Bar (on property)

9. ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,971 reviews)
"Hotel is great for the price."
United States
alex
The price is ฿3,418
฿4,063 total
includes taxes & fees
23 Nov - 24 Nov
ACME Hotel Chicago, Outset Collection by Hilton
A modern lobby with a grey sofa, checkered ottomans, and a coffee table. There are black chairs, a blue sofa, and a TV on a stand.

10. Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,325 reviews)
"Stayed during Lollapalooza and loved it."
United States
Jena
The price is ฿3,698
฿4,396 total
includes taxes & fees
23 Nov - 24 Nov
Aloft by Marriott Chicago Mag 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.
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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 Soldier Field, Navy Pier and Wrigley Field. While you're here, capture some great memories of your trip with stops at United Center and Michigan Avenue.
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.