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Popular Gay and Lesbian Vacation Packages in Chicago

2 to 5 Day Gay and Lesbian Packages

Gay and Lesbian Hotels in Chicago

Estimated price for 1 night/2 adults

Trump International Hotel & Tower Chicago
Trump International Hotel & Tower Chicago
5.0 out of 5.0 401 N Wabash Ave, Chicago, IL
Free Cancellation
$276
4.7/5 (111 reviews)

The staff knew about the area, amenities offered in the hotel and gave my group attention we come to expect from TRUMP! A gorgeous building!

Reviewed on Feb 13, 2019
Lgbt FriendlyConciergeRoomservice
Thompson Chicago
Thompson Chicago
4.5 out of 5.0 21 East Bellevue, Chicago, IL
Free Cancellation
$179
4.7/5 (117 reviews)

Great location, great rooms. Was surprised staff was somewhat indifferent and housekeeping a bit sloppy. Still love the place and would definitly go back

Reviewed on Apr 21, 2019
Lgbt FriendlyBarDining
Comfort Suites Michigan Avenue Loop
Comfort Suites Michigan Avenue Loop
3.0 out of 5.0 320 N. Michigan Avenue, Chicago, IL
Free Cancellation
$99
4.3/5 (72 reviews)

Central location, kitchen facility in the room we stayed, and the staffs were very helpful and friendly.

Reviewed on Jan 31, 2019
Lgbt FriendlyKitchenBreakfast
Best Western Plus Hawthorne Terrace Hotel
Best Western Plus Hawthorne Terrace Hotel
2.5 out of 5.0 3434 N. Broadway Avenue, Chicago, IL
Free Cancellation
$117
4.2/5 (65 reviews)

Room was nice and updated but blinds needed to be fixed

Reviewed on Feb 27, 2019
Lgbt FriendlyParkingRefrigerator
Hyatt Regency McCormick Place
Hyatt Regency McCormick Place
4.0 out of 5.0 2233 S Martin Luther King Dr, Chicago, IL
Free Cancellation
$123
4.1/5 (248 reviews)

I loved that it was attached to McCormick Place. It made it so easy!

Reviewed on Apr 17, 2019
Lgbt FriendlySportsConcierge
Hotel Versey Days Inn by Wyndham Chicago
Hotel Versey Days Inn by Wyndham Chicago
3.0 out of 5.0 644 West Diversey Parkway, Corner Diversey/Clark/Broadway, Chicago, IL
Free Cancellation
$98
4.0/5 (187 reviews)

This hotel was in an excellent location for us. Quirky and fun decor, older furniture, but completely suited our needs. I would absolutely stay here again. The staff was wonderful and always cheerful - we truly enjoyed our getaway.

Reviewed on Apr 22, 2019
Lgbt FriendlyParkingFree Wifi

Chicago Gay and Lesbian Travel

The nation’s third-largest city is a major hub for every gay or lesbian in the Midwest and a popular gay travel destination. It’s a friendly, easy-going city despite its worldly refinement. The Windy City has a huge and very visible LGBT scene, centered in two main areas: nightlife-centric Boystown (a.k.a. East Lakeview), and cozy Andersonville. Boystown is about five miles north of the downtown Loop in a triangle bounded by Belmont Avenue, Halsted Street, and Broadway. (Halsted Street has most of the gay establishments and bars.) The Swedish immigrant neighborhood of Andersonville, with many trendy cafes, eateries and furniture stores on Clark Street, was a haven for lesbians in the late 80s and early 90s but these days is equally mixed. Meanwhile, the near West Side hipster mecca of Logan Square is home to such a high number of LGBT folk that some have dubbed it Logan’s Queer. And since Chicago is home to 27 miles of lakefront, don’t miss the massive gay beach scene each summer at Hollywood Beach in Edgewater.

Chicago is justifiably famous for its architecture, and the skyline is one of the most impressive in the world, home to the massive icons of the Willis Tower and the John Hancock Building, not to mention more recent additions by Jeanne Gang and Frank Gehry. (Be sure to take one of the city’s architectural boat tours that glide up and down the Chicago River.) The Magnificent Mile along Michigan Avenue in the heart of the city is not only lined with historic buildings, but with some of the city’s best shopping as well. For great outdoor views of the city, take a ride on the new Ferris wheel at historic Navy Pier. Downtown’s Millennium Park boasts a Frank Gehry-designed amphitheater, two 50-foot video block towers with fountains, and silvery “Cloud Gate” (aka “the Bean”), the Anish Kapoor-designed sculpture that reflects the city skyline and is among the most Instagrammed pieces of public art on earth.

Travel tips


1. Head to the Hancock.

The lines are longer at the Willis Tower, and even though the John Hancock Building is not as tall, its Signature Room on the 95th floor is a great place to hang out in a lounge and sip a drink while gazing over the city and lake.

2. Visit in summer and fall.

The city is notoriously frigid in winter and springtime is usually disappointingly cold. Meanwhile, Chicagoans tend to enjoy each summer day like it’s their last on earth and September and early October are gorgeous times to visit.

3. Fly into Midway. 

O’Hare is one of the busiest and most hectic airports in the world, while the smaller and less busy Midway Airport is closer to the Loop and serves more discount airlines.

Chicago LGBT Events

International Mr. Leather (imrl.com). This full weekend of leather fetish parties and pageantry is one of the largest on earth and it’s the one time you’ll see folks on the street walking around in jock straps and harnesses. The contest itself is only for the diehard, but everyone loves the sprawling leather market and boozing and schmoozing in the lobby of the host hotel.

The city’s Pride Parade runs right through the heart of Boystown and is big—almost too big—for the ‘hood to handle. Nevertheless, the city has aimed to Chicago Pride (chicagopride.gopride.com) by spreading the festivities out over two weekends and redrawing the parade route to ease congestion. Expect nearly one million revelers each June.

Recently Reviewed Gay and Lesbian Hotels

*Savings based on all package bookings with Flight + Hotel made on Orbitz.com from January 1, 2018 to December 31, 2018 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.