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Check availability on Winnetka Gay-Friendly Hotels

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 ฿1,846
฿2,722 total
includes taxes & fees
4 Jan - 5 Jan 2026
Freehand Chicago
Cocktail bar
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 ฿2,492
฿2,926 total
includes taxes & fees
14 Jan - 15 Jan 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 ฿2,332
฿2,738 total
includes taxes & fees
28 Dec - 29 Dec
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 ฿2,448
฿3,800 total
includes taxes & fees
11 Jan - 12 Jan 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 ฿2,923
฿4,506 total
includes taxes & fees
13 Jan - 14 Jan 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Egyptian cotton sheets, premium bedding, pillow-top beds, in-room safe
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 ฿2,415
฿2,835 total
includes taxes & fees
17 Dec - 18 Dec
The Whitehall Hotel, BW Premier Collection
Ballroom
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 ฿2,561
฿3,006 total
includes taxes & fees
5 Jan - 6 Jan 2026
Hilton Chicago/Magnificent Mile Suites
Reception
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 ฿2,953
฿3,466 total
includes taxes & fees
12 Jan - 13 Jan 2026
Eurostars Magnificent Mile
Exterior
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 ฿3,060
฿4,602 total
includes taxes & fees
11 Jan - 12 Jan 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 ฿2,246
฿2,636 total
includes taxes & fees
5 Jan - 6 Jan 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

Searching for LGBTQ-friendly accommodation in Winnetka?
If you're searching for a place that will welcome you to Winnetka, Expedia has all the gay-friendly hotels you'd wish for. Discover the people, places and traditions found only in Winnetka.
What should I see while I'm in Winnetka?
During your trip, get out and enjoy everything Winnetka has to offer. You and your travelling 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 welcome all travellers who identify as LGBTQIA+. You'll find a selection of LGBTQ-friendly accommodation options on our site. In Winnetka, these hotels will provide lesbian, gay, bisexual and transgender adventurers with the information needed to design the trip of a lifetime.
What can I expect from LGBTQ-friendly accommodation in Winnetka?
Stay at a gay-friendly hotel in Winnetka and you'll be around like-minded people, so you can relax and enjoy your trip. Many of our LGBTQ-friendly accommodation options offer community-specific packages, exclusive tours and opportunities for social interaction.