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Check availability on Sleepy Hollow Gay-Friendly Hotels

This weekend
4 Sep - 6 Sep
Next weekend
11 Sep - 13 Sep

Our top choices for Sleepy Hollow LGBT-friendly hotels

A modern bar area with a bar counter, seating, and large windows offering a view of the street.

1. Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
2.5 star property
West Lawn
8.0 out of 10, Very good, (1,003 reviews)
"Our stay was good"
United States
Diane
The price is ฿4,312
฿5,391 total
includes taxes & fees
8 Sept - 9 Sept
Holiday Inn Chicago – Midway Airport S by IHG
A spacious lobby with a patterned carpet, comfortable seating, a fireplace, and large windows.

2. Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,137 reviews)
"Very nice place would stay again"
United States
Konner
The price is ฿5,614
฿7,648 total
includes taxes & fees
10 Sept - 11 Sept
Hilton Chicago
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

3. 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, (2,147 reviews)
"Great stay"
United States
Dhannetta
The price is ฿5,332
฿6,339 total
includes taxes & fees
10 Sept - 11 Sept
Hilton Garden Inn Chicago Downtown South Loop
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, (2,686 reviews)
"Nice place to stay"
United States
Ashraf
The price is ฿6,021
฿8,303 total
includes taxes & fees
8 Sept - 9 Sept
Sable at Navy Pier Chicago, Curio Collection by Hilton
A modern kitchen with a large window, a dining area, and a view of the sea.

5. 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, (2,450 reviews)
"Clean, friendly staff, quick valet, and a decent breakfast"
United States
AMBER
The price is ฿5,740
฿6,825 total
includes taxes & fees
7 Sept - 8 Sept
Homewood Suites by Hilton Chicago Downtown South Loop
A multi-story hotel with a prominent sign reading "Crowne Plaza."

6. 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, (2,593 reviews)
"Loved our stay"
Canada
Jaclyn
The price is ฿6,405
฿7,616 total
includes taxes & fees
7 Sept - 8 Sept
Crowne Plaza Chicago West Loop by IHG
A spacious lobby with a checkered floor, a large sofa, and multiple chairs.

7. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
3.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,010 reviews)
"Clean rooms and good breakfast"
United States
Sarwat
The price is ฿4,383
฿5,210 total
includes taxes & fees
7 Sept - 8 Sept
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
A modern hotel lobby with a reception desk, marble flooring, and elegant chandeliers.

8. Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,374 reviews)
"Great location."
United States
Xiao
The price is ฿5,197
฿7,192 total
includes taxes & fees
7 Sept - 8 Sept
Silversmith Hotel Chicago Downtown
A hotel entrance with a glass door, a sign above the door, and two potted plants on either side.

9. Hampton Inn Majestic Chicago Theatre District

Hampton Inn Majestic Chicago Theatre District
3.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,000 reviews)
"Great stay, super clean"
United States
Richard
The price is ฿6,208
฿7,381 total
includes taxes & fees
7 Sept - 8 Sept
Hampton Inn Majestic Chicago Theatre District
The Claridge House building with a sign, American and another flag, and outdoor seating with umbrellas.

10. 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, (1,443 reviews)
"Nice upscale hotel in a great area."
United States
Christie
The price is ฿4,336
฿6,130 total
includes taxes & fees
7 Sept - 8 Sept
Claridge House Chicago, Tapestry Collection by Hilton
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.