If you want to find the cultural center of the gay community in the U.S. Midwest, look no further than the third largest city in the United States, Chicago. Boystown Chicago, the neighborhood otherwise known as East Lakeview or Northalsted, is the largest gay neighborhood in the city. Located between Halsted Street, Broadway and Belmont Avenue, Boystown Chicago has a lot going on all year long, with the highlights being the Northalsted Halloween Parade, the Northalsted Market Days and Chicago Pride Fest.
While you are in Boystown, do make sure you check out some of the local venues. Start with the well established Sidetrack, a mainstay of Chicago gay nightlife for over 30 years, where you'll enjoy the many video monitors playing pop tunes and the gorgeous beer garden on the roof. Since you are already in Boystown Chicago, head over to Roscoe's which plays non-stop dance music, serves food in the attached cafe and holds a memorable wet underwear contest on the last Thursday of each month. Next, stop at Hydrate, a nearby lounge and dance club that usually doesn't start charging a cover until midnight. Other options in Boystown Chicago include Berlin, Minibar Ultra Lounge & Cafe, Cellblock and Circuit and many, many more.
The second largest gay neighborhood in Chicago is the relatively quaint and chilled-out district of Andersonville, the center of which can be found at Berwyn and Clark. The perimeter of the Andersonville district is generally formed by Ainslie, Victoria, Ravenswood and Magnolia and it is the home of several gay bars, one bathhouse and the annual music, food and entertainment festival called Midsommarfest.
For Andersonville gay bars, take a look at Atmosphere for the drag show, the almost-nude dancers, the large dance floor and the excellent drink specials. You might also enjoy Marty's Martini Bar or Sofo.
If you are lucky enough to be in Chicago during the summer, you must go to Hollywood Beach, the most popular beach for all people who are gay or who appreciate gays. Recently renamed Kathy Osterman Beach, the south side of the beach is where the gays tend to hang out. You will likely find the biggest crowds at the beach on Sundays.
There are numerous gay events held in Chicago throughout the year. As is typical in any major American city, Gay Pride Fest is a huge event held in June. However, Chicago has other events that should not be missed, including Bear Pride and International Mr. Leather in May, as well as Reeling: The Chicago LGBTQ and International Film Festival held in September.