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Check prices for these dates

Tonight
11 Nov - 12 Nov
Tomorrow
12 Nov - 13 Nov
This weekend
13 Nov - 15 Nov
Next weekend
20 Nov - 22 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
8.8 out of 10, Excellent, (1,386 reviews)
"Really enjoyed my stay. Will definitely stay there again"
United States
RENE
The price is ฿4,108
฿4,826 total
includes taxes & fees
12 Dec - 13 Dec
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
A grand hotel facade with classical architecture, featuring tall columns, ornate detailing, and a prominent entrance with a marquee.

2. 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, (1,616 reviews)
"We had a lovely stay!"
Netherlands
lieneke
The price is ฿3,662
฿4,354 total
includes taxes & fees
22 Nov - 23 Nov
Hyatt House Chicago Medical/University District
A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.

3. William Tell Hotel MOD Collection by Sonesta

William Tell Hotel MOD Collection by Sonesta
3.5 star property
Countryside
8.0 out of 10, Very good, (1,698 reviews)
"Great stay and will definitely be back!"
United States
Elizabeth
The price is ฿3,266
฿3,657 total
includes taxes & fees
22 Nov - 23 Nov
William Tell Hotel MOD Collection by Sonesta
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, (2,783 reviews)
"Best stay, wonderful property."
Canada
Bonnie
The price is ฿4,372
฿6,349 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, (2,202 reviews)
"Great place to stay at"
United States
Aran
The price is ฿3,236
฿3,848 total
includes taxes & fees
23 Nov - 24 Nov
Hilton Garden Inn Chicago Downtown South Loop
The entrance to Homewood Suites at Hilton, featuring a modern glass facade, a sign indicating the address as 59 East, and a logo with a bird and the name 'Homewood Suites'.

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, (2,532 reviews)
"Wonderful room and great breakfast buffet!"
United States
Nicole
The price is ฿3,520
฿4,185 total
includes taxes & fees
23 Nov - 24 Nov
Homewood Suites by Hilton Chicago Downtown South Loop
A reception area with two desks, a large abstract wall art, and a view of the city through large windows.

7. Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,274 reviews)
"good breakfast, friendly staff"
United States
Donna
The price is ฿3,373
฿4,411 total
includes taxes & fees
23 Nov - 24 Nov
Holiday Inn & Suites Chicago - Downtown by IHG
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, (2,816 reviews)
"Wonderful stay!"
United States
Dejai
The price is ฿3,841
฿4,567 total
includes taxes & fees
22 Nov - 23 Nov
Crowne Plaza Chicago West Loop by IHG
A bar area with a checkered floor, bar stools, and a well-lit sign above the bar.

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, (1,963 reviews)
"Hotel is great for the price."
United States
alex
The price is ฿2,851
฿3,390 total
includes taxes & fees
7 Dec - 8 Dec
ACME Hotel Chicago, Outset Collection by Hilton
A modern hotel lobby with round tables, blue upholstered chairs, and large windows offering a view of the outdoors.

10. Hampton Inn Chicago-O'Hare International Airport

Hampton Inn Chicago-O'Hare International Airport
2.5 star property
Schiller Park
9.4 out of 10, Exceptional, (2,410 reviews)
"conveniently located close to airport- 10 min. Free breakfast!"
United States
Danielle
The price is ฿3,362
฿3,866 total
includes taxes & fees
23 Nov - 24 Nov
Hampton Inn Chicago-O'Hare International Airport
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

Compare popular hotels in Sleepy Hollow

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A modern interior with a staircase, green upholstered seating, and artwork on the walls.
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
2.5 star property
8.8
Excellent
1,386 reviews
View
A grand hotel facade with classical architecture, featuring tall columns, ornate detailing, and a prominent entrance with a marquee.
Hyatt House Chicago Medical/University District
3.5 star property
9.2
Wonderful
1,616 reviews
View
A restaurant with a long counter, booths, and hanging light fixtures.
William Tell Hotel MOD Collection by Sonesta
3.5 star property
8.0
Very good
1,698 reviews
View
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
9.4
Exceptional
2,783 reviews
View
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.
Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
8.8
Excellent
2,202 reviews
View

Top Sleepy Hollow Hotel Reviews

A Hampton Inn by Hilton building with a large parking lot and a clear sky.
Hampton Inn Chicago-O'Hare International Airport

Hampton Inn Chicago-O'Hare International Airport

Hampton Inn Chicago-O'Hare International Airport
Schiller Park

10/10 Excellent

Very clean….lovely staff…wanted for nothing…breakfast a great bonus..shuttle to airport so convenient…
United Kingdom
Carole
Reviewed July 23, 2026
Hampton Inn Chicago-O'Hare International Airport

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.