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Check availability on Uptown Gay-Friendly Hotels

Our top choices for Uptown LGBT-friendly hotels

Cocktail bar
Freehand Chicago

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very good, (2643)
"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
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 ฿2,492
฿2,926 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, (2746)
"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
Lobby
River Hotel

River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (4855)
"Great location, comfortable room, and nice staff."
United States
Claudia
The price is ฿2,624
฿3,080 total
includes taxes & fees
16 Dec - 17 Dec
River Hotel
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, (3485)
"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
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 ฿2,415
฿2,835 total
includes taxes & fees
17 Dec - 18 Dec
The Whitehall Hotel, BW Premier Collection
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
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 ฿3,060
฿4,602 total
includes taxes & fees
11 Jan - 12 Jan 2026
The Allegro Royal Sonesta Hotel Chicago Loop
Reception hall
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3157)
"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
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 Uptown Hotel Reviews

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Frequently asked questions

How do I find a gay-friendly hotel in Uptown?
If you're interested in booking a place that will welcome you to Uptown, Expedia has all the LGBTQ-friendly hotels you'd wish for. Discover the people, places and traditions found only in Uptown.
What is there to see in Uptown?
During your trip, get out and enjoy everything Uptown has to offer. You and your travelling companions may want to visit Lake Michigan, Aragon Ballroom and Riviera Theatre. While you're here, create some great memories of your trip with stops at Montrose Beach, Montrose Harbor and Aragon Entertainment Center.
What is an LGBTQ-friendly hotel in Uptown?
LGBTQ-friendly hotels welcome all travellers who identify as LGBTQIA+. Expedia has compiled a selection of LGBTQ-friendly hotels worldwide. In Uptown, 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 a gay-friendly hotel in Uptown?
Stay at a gay-friendly hotel in Uptown and get a warm welcome from a community you belong to. 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.