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.
Located in Lakeview, this hotel is within 6 mi (10 km) of Briar Street Theatre, Wrigley Field, and Lincoln Park Zoo. John Hancock Center and Water Tower Place are also within 6 mi (10 km).
Located in The Loop, this aparthotel is steps from Chicago Riverwalk and Michigan Avenue. Art Institute of Chicago and Chicago Theatre are also within 6 mi (10 km).
In Chicago's lively Lakeview neighborhood, this award-winning Days Inn is about 1 mile from Lincoln Park, the Lincoln Park Zoo, Wrigley Field, and the Peggy Notebaert Nature Museum. Downtown Chicago is 3 miles south.
Connected via enclosed skybridge to the McCormick Place convention complex, the Hyatt Regency is adjacent to a Metro station, with easy access to Chicago's downtown hub. Soldier Field, the home of the Chicago Bears, is a 15 minute walk away.
Right on Magnificent Mile, The James Chicago-Magnificent Mile puts guests in the middle of Chicago's famed shopping district filled with boutiques and restaurants. A 5-minute drive is all it takes to get to Millennium Park or the Museum of Contemporary Art.
This chic, 22-story Chicago hotel is 2 blocks from Lake Michigan and the Magnificent Mile; numerous shops, bars, and nightclubs are within a 3-block radius.
Set in Chicago, this family-friendly hotel is within 6 mi (10 km) of State Street, Navy Pier, and John G. Shedd Aquarium. Lincoln Park Zoo and Skydeck Ledge are also within 6 mi (10 km).
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.
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.
*Savings based on all package bookings with Flight + Hotel made on Orbitz.com from October 2017 through September 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.