Search Gay-Friendly Hotels in Kenwood

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Kenwood Gay-Friendly Hotels

Our top choices for Kenwood LGBT-friendly hotels

Cocktail bar
Freehand Chicago

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very good, (2640)
"The room was spotless and the staff where great!"
United States
Maria
The price is Rp973.791
Rp1.436.245 total
includes taxes & fees
4 Jan - 5 Jan 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 Rp1.315.034
Rp1.543.717 total
includes taxes & fees
14 Jan - 15 Jan 2026
Aloft Chicago Mag Mile
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, (2744)
"Clean room and friendly staff, overall good stay "
United States
eesaa saalik
The price is Rp1.291.730
Rp2.005.011 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, (2260)
"This place was amazing !"
United States
Jayla Danyell
The price is Rp1.542.418
Rp2.377.441 total
includes taxes & fees
13 Jan - 14 Jan 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Lobby
River Hotel

River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (4854)
"Great location, comfortable room, and nice staff."
United States
Claudia
The price is Rp1.384.281
Rp1.625.008 total
includes taxes & fees
15 Dec - 16 Dec
River Hotel
2 bars/lounges
Hyatt Regency Chicago

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3393)
"I always love staying at this place when I visit"
Canada
William
The price is Rp2.263.856
Rp3.146.100 total
includes taxes & fees
28 Dec - 29 Dec
Hyatt Regency Chicago
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, (3483)
"Great place to stay "
United States
RaShawna
The price is Rp1.351.322
Rp1.586.317 total
includes taxes & fees
5 Jan - 6 Jan 2026
Hilton Chicago/Magnificent Mile Suites
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 Rp1.274.228
Rp1.495.815 total
includes taxes & fees
18 Dec - 19 Dec
The Whitehall Hotel, BW Premier Collection
Reception hall
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3152)
"Amazing stay very clean and beautiful views "
United States
Deigo
The price is Rp1.558.066
Rp1.829.014 total
includes taxes & fees
12 Jan - 13 Jan 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, (2292)
"Great stay"
United States
Jeremy
The price is Rp1.614.662
Rp2.428.124 total
includes taxes & fees
11 Jan - 12 Jan 2026
The Allegro Royal Sonesta Hotel Chicago 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.
View all properties

Top Kenwood Hotel Reviews

Explore a world of travel with Expedia

Frequently asked questions

How do I find a gay-friendly hotel in Kenwood?
If you're interested in booking a place that will welcome you to Kenwood, Expedia has all the LGBTQ-friendly hotels you'd wish for. Travellers are often drawn to Kenwood for its beaches and restaurants.
What is there to see in Kenwood?
During your trip, get out and enjoy everything Kenwood has to offer. You and your travelling companions may want to visit Lake Michigan, 4944 S Woodlawn Ave and Obama's House. While you're here, create some great memories of your trip with stops at Barack Obama Residence, Hyde Park Art Center and Elijah Muhammad House.
What is an LGBTQ-friendly hotel in Kenwood?
LGBTQ-friendly hotels, also known as gay-friendly hotels, welcome all travellers who identify as LGBTQIA+. Expedia has compiled a selection of LGBTQ-friendly hotels worldwide. In Kenwood, these hotels prioritise a diverse environment in which guests are welcomed, respected and not obliged to declare or hide their sexual orientation.
What can I expect from an LGBTQ-friendly Kenwood hotel?
Stay at a gay-friendly hotel in Kenwood and the staff will help you explore the local gay scene and the LGBTQ+ culture. Some of Expedia's LGBTQ-friendly hotels go the extra mile and offer concierge services that provide information about nearby LGBTQ restaurants and local events.