Find Gay friendly Hotels in Winnetka, IL

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Our top choices for Winnetka LGBT-friendly hotels

Cocktail bar
Freehand Chicago

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very Good, (2642)
"The room was spotless and the staff where great!"
United States
Maria
The price is ₩86,446
₩127,499 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Freehand Chicago
Lobby
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 ₩116,739
₩137,039 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Aloft Chicago Mag Mile
Lobby sitting area
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1983)
"A good place for stay "
United States
Julio
The price is ₩109,232
₩128,227 total
includes taxes & fees
Dec 28 - Dec 29
Club Quarters Hotel Wacker at Michigan, Chicago
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, (2745)
"Clean room and friendly staff, overall good stay "
United States
eesaa saalik
The price is ₩113,488
₩176,601 total
includes taxes & fees
Jan 11 - Jan 12, 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 ₩136,925
₩211,052 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Bar (on property)
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 ₩113,117
₩132,789 total
includes taxes & fees
Dec 17 - Dec 18
The Whitehall Hotel, BW Premier Collection
View from room
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, (3484)
"Great place to stay "
United States
RaShawna
The price is ₩119,960
₩140,822 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hilton Chicago/Magnificent Mile Suites
Reception hall
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3154)
"Amazing stay very clean and beautiful views "
United States
Deigo
The price is ₩138,314
₩162,367 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Eurostars Magnificent Mile
Lobby
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, (2295)
"Great stay"
United States
Jeremy
The price is ₩143,338
₩215,549 total
includes taxes & fees
Jan 11 - Jan 12, 2026
The Allegro Royal Sonesta Hotel Chicago Loop
Pool
Hilton Garden Inn Chicago Downtown South Loop

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, (1756)
"Clean and staff was courteous. "
United States
HANNAH
The price is ₩105,213
₩123,492 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hilton Garden Inn Chicago Downtown South 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 Winnetka Hotel Reviews

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Frequently asked questions

How do I find a gay-friendly hotel in Winnetka?
If you're interested in booking a place to relax, refresh, and recharge in Winnetka, our website has the gay-friendly hotel you're looking for. Discover the people, places, and traditions found only in Winnetka.
What are the top places to visit in Winnetka?
During your trip, get out and enjoy all that Winnetka is known for. You and your traveling companions may want to visit Lake Michigan, Chocolate Box, and Maple Street Beach. While you're here, create some great memories of your trip with a stop at Elder Lane Beach.
What is an LGBTQ-friendly hotel in Winnetka?
LGBTQ-friendly hotels are places where lesbian, gay, bisexual, and transgender travelers are proudly welcomed. Expedia has worked with the International Gay and Lesbian Travel Association (IGLTA) to compile a selection of LGBTQ-friendly hotels worldwide. In Winnetka, hotels affiliated with IGLTA will provide lesbian, gay, bisexual, and transgender adventurers with the information needed to design the trip of a lifetime.
What can I expect from an LGBTQ-friendly accommodation in Winnetka?
Stay at a gay-friendly hotel in Winnetka and the staff will help you explore the local gay scene and the LGBTQ+ culture. Many of our LGBTQ-friendly accommodations offer concierge services that provide information about nearby LGBTQ restaurants and local events.