Gay friendly Hotels in Winnetka

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Check prices for these dates

Tonight
14 Nov - 15 Nov
Tomorrow
15 Nov - 16 Nov
Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov

Our top choices for Winnetka LGBT-friendly hotels

A large, modern hotel with a prominent American flag, a covered entrance, and a parking lot.

1. Hampton Inn & Suites Chicago-North Shore/Skokie

Hampton Inn & Suites Chicago-North Shore/Skokie
3.0 star property
Skokie
9.2 out of 10, Wonderful, (1,098 reviews)
"Great stay, breakfast and clean rooms. I would stay here again"
United States
Peter
The price is S$180
includes taxes & fees
30 Nov - 1 Dec
Hampton Inn & Suites Chicago-North Shore/Skokie
A hallway with large, illuminated wall panels and a tiled floor.

2. Holiday Inn Chicago North-Evanston by IHG

Holiday Inn Chicago North-Evanston by IHG
3.0 star property
Downtown Evanston
8.6 out of 10, Excellent, (2,174 reviews)
"Very clean and great location near restaurants. We’d stay here again."
United States
MICHELLE
The price is S$152
includes taxes & fees
13 Dec - 14 Dec
Holiday Inn Chicago North-Evanston by IHG
A hotel room with a bed, a desk with a television, a chair, a lamp, and a door leading to another room.

3. Best Western Glenview -Chicagoland Inn and Suites

Best Western Glenview -Chicagoland Inn and Suites
2.5 star property
Glenview
8.8 out of 10, Excellent, (1,269 reviews)
"Clean and spacious rooms, Friendly staff, reasonable breakfast,good location,"
United States
Praveen
The price is S$127
includes taxes & fees
23 Nov - 24 Nov
Best Western Glenview -Chicagoland Inn and Suites
A spacious lobby with multiple seating areas, a reception desk, and flags representing various organizations.

4. La Quinta Inn & Suites by Wyndham Bannockburn-Deerfield

La Quinta Inn & Suites by Wyndham Bannockburn-Deerfield
3.0 star property
Deerfield
9.0 out of 10, Wonderful, (1,003 reviews)
"Stayed here for my son's Navy graduation and had a very good experience and breakfast was always ready and hot every morning."
United States
Lillian
The price is S$124
includes taxes & fees
13 Dec - 14 Dec
La Quinta Inn & Suites by Wyndham Bannockburn-Deerfield
An outdoor patio with wicker furniture, a pergola, and a view of the cityscape.

5. Hampton Inn & Suites Rosemont Chicago O'Hare

Hampton Inn & Suites Rosemont Chicago O'Hare
3.5 star property
Rosemont
9.4 out of 10, Exceptional, (1,170 reviews)
"Very nice staff and very clean rooms"
United States
Isabel
The price is S$179
includes taxes & fees
24 Nov - 25 Nov
Hampton Inn & Suites Rosemont Chicago O'Hare
A three-tiered fruit basket on a wooden table against a wall with framed pictures.

6. Heart O' Chicago

Heart O' Chicago
2.0 star property
Edgewater
7.8 out of 10, Good, (1,001 reviews)
"Room was basic but clean, great value for location, plus free parking onsite"
United States
Zina
The price is S$162
includes taxes & fees
15 Dec - 16 Dec
Heart O' Chicago
A hotel room with a TV, a wooden desk, a chair, a sofa, and a small table.

7. Comfort Suites Chicago O'Hare Airport

Comfort Suites Chicago O'Hare Airport
3.0 star property
Schiller Park
7.8 out of 10, Good, (3,243 reviews)
"Place was great!"
United States
Michael
The price is S$129
includes taxes & fees
26 Nov - 27 Nov
Comfort Suites Chicago O'Hare Airport
A Holiday Inn Express & Suites hotel with a modern design, featuring a brick facade and multiple windows.

8. Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

Holiday Inn Express & Suites Chicago O'Hare Airport by IHG
3.0 star property
Des Plaines
8.8 out of 10, Excellent, (2,090 reviews)
"Clean quiet room, friendly staff and convenient location!"
United States
Jaishiri
The price is S$169
includes taxes & fees
13 Dec - 14 Dec
Holiday Inn Express & Suites Chicago O'Hare Airport by IHG
A lobby with a grey sofa, a yellow armchair, and a coffee table.

9. Sonesta Chicago O'Hare Airport Rosemont

Sonesta Chicago O'Hare Airport Rosemont
3.0 star property
Rosemont
8.8 out of 10, Excellent, (1,659 reviews)
"Great hotel, nice stagf"
United States
Charles
The price is S$201
includes taxes & fees
23 Nov - 24 Nov
Sonesta Chicago O'Hare Airport Rosemont
A bar area with a long counter, multiple bar stools, and a television screen.

10. Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
3.5 star property
Rosemont
8.6 out of 10, Excellent, (2,915 reviews)
"great hotel"
United States
JACKIE
The price is S$161
includes taxes & fees
27 Nov - 28 Nov
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
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

A bar area with a long counter, multiple stools, and shelves stocked with bottles.
L7 CHICAGO by LOTTE HOTELS

L7 CHICAGO by LOTTE HOTELS

L7 CHICAGO by LOTTE HOTELS
Downtown Chicago

10/10 Excellent

A very nice property with an excellent location. The Korean restaurant on the ground floor was a pleasant surprise and served very tasty food. The only downside was that one of the two lifts was out of service for the entire four nights of my stay, which led to longer wait times and was somewhat frustrating.
Singapore
Sungwon
Reviewed June 21, 2026
L7 CHICAGO by LOTTE HOTELS

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, Maple Street Beach and Elder Lane Beach. While you're here, capture some great memories of your trip with stops at Wrigley Field, Navy Pier and Michigan Avenue.

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.

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