Gay Vacations in Chicago, Illinois

Dusk over Buckingham Memorial Fountain in Chicago, Illinois
Buckingham Memorial Fountain in Chicago, Illinois (Brand X)

Chicago Highlights

  • Head to the Hancock. The lines are longer at the Sears 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.
  • Take a LGBT tour. The city's tourism office offers free volunteer-led neighborhood tours, including gay tours of Boystown and Andersonville.
  • 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.

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: Boystown (a.k.a. Lakeview), and lesbian-popular 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 boutiques and bars on Clark Street, has been renovated by the resident lesbians. Wicker Park is also emerging as an artsy queer-friendly area as well. And since Chicago is perched on the sandy southwest shores of Lake Michigan, there’s a burgeoning summer gay beach scene at Lake Shore Drive and Hollywood Avenue. Chicago is big into leather and bears, with the huge and infamous International Mister Leather happening here every May. Among other top events for LGBT travel, Pride is in June, and there's a fun Windy City Rodeo in August. Northalsted Market Days in August is the largest two-day outdoor street festival in the Midwest, with hundreds of vendors and musical acts for which the local gays come out in force.

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 Sears Tower and the John Hancock Building, not to mention more recent additions by Rem Koolhaas 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 huge Ferris wheel at historic Navy Pier. Downtown's new Millennium Park boasts a Frank Gehry-designed amphitheater, two 50-foot video block towers with fountains, and the silvery "Cloud Gate" (called "The Bean" by locals), an Anish Kapoor-designed sculpture that reflects the city skyline.

Chicago is a museum capital as well: The Art Institute of Chicago is brimming with impressionist masterpiece, and the Field Museum of Natural History showcases the biggest T-rex fossil ever discovered. Chicago also has one of the nation’s best theater scenes, home to Steppenwolf and Second City, with an annual Broadway in Chicago series.

Published: 16 Jul 2008 | Last Updated: 17 Aug 2012
Details mentioned in this article were accurate at the time of publication


Sign up to Away's Travel Insider

Preview newsletter »

Package Trips: