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Our top choices for Sleepy Hollow LGBT-friendly hotels

Terrace/patio

1. 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, (2,654 reviews)
"Great stay."
United States
Dawn
The price is ฿5,691
฿7,908 total
includes taxes & fees
7 Sept - 8 Sept
Sable at Navy Pier Chicago, Curio Collection by Hilton
Restaurant

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, (1,015 reviews)
"Our stay was good"
United States
Diane
The price is ฿3,778
฿4,767 total
includes taxes & fees
8 Sept - 9 Sept
Holiday Inn Chicago – Midway Airport S by IHG
Exterior

3. Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,059 reviews)
"Great location, amazing staff"
United States
Brenda
The price is ฿5,606
฿7,638 total
includes taxes & fees
7 Sept - 8 Sept
Hilton Chicago
Exterior

4. La Quinta Inn & Suites by Wyndham Chicago Downtown

La Quinta Inn & Suites by Wyndham Chicago Downtown
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,885 reviews)
"Location, good stay"
United States
Shilpa
The price is ฿4,743
฿6,230 total
includes taxes & fees
8 Sept - 9 Sept
La Quinta Inn & Suites by Wyndham Chicago Downtown
Interior detail

5. Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1,175 reviews)
"Great location and easy public transportation to explore the city and Wrigley field. Lovely room with great view."
United States
Beth
The price is ฿3,947
฿5,675 total
includes taxes & fees
7 Sept - 8 Sept
Staypineapple, An Iconic Hotel, The Loop
Suite, 1 Bedroom, Corner | Private kitchen | Coffee/tea maker, full-sized fridge, microwave, stovetop

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, (2,429 reviews)
"Great place to stay with kids. Nice sized rooms, walking distance to museums, and nice pool."
United States
Mary
The price is ฿5,184
฿6,163 total
includes taxes & fees
7 Sept - 8 Sept
Homewood Suites by Hilton Chicago Downtown South Loop
Restaurant

7. Hilton Garden Inn Chicago Central Loop

Hilton Garden Inn Chicago Central Loop
3.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,399 reviews)
"Very nice would stay again"
United States
Dawn
The price is ฿5,606
฿6,666 total
includes taxes & fees
7 Sept - 8 Sept
Hilton Garden Inn Chicago Central Loop
Exterior

8. 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, (1,450 reviews)
"Just really like this stay and location is fantastic!"
United States
Timothy
The price is ฿3,778
฿5,464 total
includes taxes & fees
7 Sept - 8 Sept
Claridge House Chicago, Tapestry Collection by Hilton
Exterior

9. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (2,957 reviews)
"Great location!"
United States
JENNIFER
The price is ฿5,155
฿7,102 total
includes taxes & fees
1 Sept - 2 Sept
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Exterior

10. Hampton Inn Chicago West Loop Fulton Market Area

Hampton Inn Chicago West Loop Fulton Market Area
2.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,008 reviews)
"Clean, breakfast was good. Perfect for a quick trip. Would stay again!"
United States
Karen
The price is ฿5,843
฿6,947 total
includes taxes & fees
7 Sept - 8 Sept
Hampton Inn Chicago West Loop Fulton Market Area
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

Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

10/10 Excellent
"Beautiful stay"
Ashley 1-night trip
Posted 8 hours ago
Hyatt Regency McCormick Place Chicago

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