The Chicago Pride Parade is one of the most highly attended festivals of its kind on the planet, pulling in something like a million revelers every year. No surprise really, given Chicago is one of the most LGBTQ-friendly cities in the States, its Northalsted neighborhood (aka Boystown) a vibrant community hub that was the first in the country to be officially recognized as a gay village. The city’s colorful month-long June Pride party is, as you might expect, a fairly flamboyant affair, taking in karaoke nights, drag brunches, art shows, skate parties, marching bands, club nights and much more. Raise your rainbow flag and read on for our guide to some of the best things to do in Chicago during Pride month.
Spend the Day in Boystown
There’s no better way to familiarize yourself with Chicago’s LGBTQ+ history and culture than with a visit to the Legacy Walk in Boystown. Take a stroll along the North Halsted Street Corridor between Belmont Avenue and Grace Street, where this unique open-air museum takes the form of 35-or-so steel ‘rainbow pylons’. Each standing 25 feet tall, the pylons act as monuments to those legends who helped shape the LGBTQ+ movement in Chicago and beyond, with bronze plaques commemorating individuals including James Baldwin, Josephine Baker, Harvey Milk, Oscar Wilde, Jose Sarria and Freddie Mercury, plus pivotal events like the 1969 Stonewall Riots.
Afterwards, make time to check out some of the neighborhood’s other beloved LGBTQ+ hotspots, including the Center on Halsted, a community hub that’s home to the Hoover-Leppen Theater and Billie Jean King Recreation Hall among other facilities. Head up to the roof for tip-top neighborhood views that become yet more colorful during Pride month, thanks to the increased proliferation of rainbow flags and bunting that decorate the streets below.
Hungry? You’re in luck. Boystown also happens to be home to some of the best brunch spots in town. Hit up local institution Drew’s on Halsted for eggs every which way accompanied by breakfast martinis and live DJs. Or mosey on over to the smart, literary Wilde Bar & Restaurant, named after guess who?
Of course, the LGBTQ+ nightlife in this lively enclave is just about as good as it gets, running the gamut from karaoke parties to dive bars, drag nights and hedonistic all-night dance parties. Try Sidetrack, The Closet, Roscoe's, Hydrate and the Kit Kat Lounge for some of the very best.
LGBTQ+ Art & Culture
There’s plenty more going across Chicago through the month of June. Check press listings for comedy, cabaret and drag performances hosted by the likes of Boystown stalwarts the Newport Theater, Dorothy and the Whiskey Girl Tavern.
Many of the city’s largest cultural institutions also run LGBTQ-themed programs and exhibitions during Pride month. For example, the Field Museum, one of the biggest and best natural history museums in the world, hosts an annual drag pageant as well as events around the role of sex and gender in the natural world.
Meanwhile, the American Writers Museum runs readings, workshops and tours spotlighting the work of LGBTQ+ authors whose writings are exhibited here, including the likes of James Baldwin, Maurice Sendak and Susan Sontag. There are events for kids at Chicago Public Library branches including Logan Square and South Shore, with drag and rainbow story times to keep the little ‘uns entertained, and an annual party down at Navy Pier, which is usually held the day before the Pride march. It’s an all-day event that features live music, marching bands, DJs and more, and is conveniently close to all those seaside fairground rides for a spot of old-school fun and relaxation between bouts of dancing!
General admission to a number of these attractions (plus many more tours and activities around Chicago) are included with a Go Chicago pass. You could save up to 50% on entry to the likes of Navy Pier, the Field Museum, the Shedd Aquarium, 360 Chicago and more. Note that additional tickets may be required for entry to some Pride-themed events.
Find out more about the Go Chicago pass and get yours here.
The Pride Parade and Festival
As the climax of Chicago’s Pride month approaches, all attention turns towards Chicago Pride Fest and the annual parade. The Parade takes place on the last Sunday of June with Pride Fest traditionally falling on the Friday and Saturday of the same weekend (or sometimes the weekend before). Pride Fest gets the party started in earnest with two days of live performances across three stages, everything from international pop stars to the very best of Chicago’s DJ and drag scenes. Add to that 150+ food and beverage vendors and you have all the ingredients you require for a top shindig. The festival takes place on Halsted Street, from Addison to Grace St, and is free to enter, though there’s a suggested $15 donation to help pay performers and festival workers, as well as supporting local community programs. Big-name stars to grace the stages here include M People’s Heather Small, Natasha Bedingfeld, Chaka Khan, and the Chicago Gay Men’s Chorus.
Find out more about this year’s Pride Fest, including the entertainment line-up, here.
The main event takes place on the last Sunday of the month, and draws the biggest crowds of the month. The Chicago Pride Parade sets off from around Sheridan and Broadway at 11AM, painting a rainbow across Northalsted as it weaves its way along and around Halsted to Lincoln Park – a distance of over six kilometers. Nab your spot to watch as dozens of flamboyant floats, revelers in outlandish costumes and live performers cruise past, complete with marching bands, stilt walkers, drag kings and queens, and more. The area surrounding Belmont and Addison stations tends to get the most busy, so arrive early if you want a decent view, or bodyswerve it altogether if claustrophobic crowds ain’t your thang. Rest assured there are plenty less densely packed locations: you’ll find for example that you have a little more breathing space towards the start of the route, and on its east side.
Find about more about this year’s Chicago Pride Parade here.
Save on Chicago’s Most Popular Attractions
Don’t miss the opportunity to check out some of Chicago’s top tours, activities and attractions while you’re in town. You could save up to 50% with a Go Chicago pass. Find out more and choose yours here.
