Gay-friendly Illinois: LGBTQ Guide to Chicago: The Windy City Heats Up This Spring and Summer

By @ 05/07/19 in Chicago, Gay Illinois, Gay travel, Gay-Friendly, Gay-friendly Illinois, Illinois, LGBT Illinois, Travel

LGBTQ guide Chicago in ManAboutWorld gay travel magazineLGBTQ Guide Chicago: Looking for a warm-weather getaway that offers a bustling urban environment, sprawling green spaces, public parks, and a sandy beach, steps from the skyline? Head to the heartland to experience Chicago’s thriving LGBTQ offerings

Each of Chicago’s 77 neighborhoods offer distinct character and personality, with culture and history interconnecting to create a vibrant tapestry of community life.

Chicago has long been an epicenter for queer culture and Lakeview’s Boystown (the U.S.’s first recognized gay village) section remains one of the most vibrant gayborhoods in the nation. With dozens of queer bars, venues, and monuments, the neighborhood is a haven for LGBTQ residents and visitors. Its history of queer icons — from literary heroes like Lorraine Hansberry and Jane Addams to gay rights activists such as Henry Gerber — is inspiring. Their stories can be discovered on a self-guided LGBTQ Landmark Tour and provide a terrific frame of reference for what has become a robust LGBTQ community.

This summer, on June 29, Chicago will make queer history with the first-ever Pride in the Park Chicago in Grant Park. The event will feature celebrations of love and protest, live music performances by international and local talent, top queens from RuPaul’s Drag Race, artisanal food vendors and a fireworks show. About 15,000 are expected to attend.

The summer of LGBTQ also includes International Mr. Leather. From May 23-27, leather-bound attendees will descend upon the city, letting their freak flags fly, and capping off the festivities with the Black and Blue Party on Monday.

Early June will see the ANDERSONVILLE MIDSOMMARFEST. The Andersonville neighborhood is one of the most LGBTQ+-friendly in Chicago, and Midsommarfest is a street festival for the arts, retail, music and more in the area.

The BACK LOT BASH runs from June 28 – 30 (butting up against Pride in the Park this year) kicking off with a safe space for families to celebrate pride followed by a two-day outdoor music festival. The event is now in its 16th year and is one of the best-attended lesbian Pride events.

And finally, come end of June, the free and fabulous NAVY PIER PRIDE on June 29. The event consists of a full day of family-LGBTQ guide Chicago in ManAboutWorld gay travel magazinefriendly festivities in honor of the LGBTQ+ community. This event includes Storytime with Drag Queens, live performances, special film presentations, and a new “Queer the Pier” fashion and music show headlined by special guest CeCe Penistone.

Thanks to an easy-to-navigate elevated rail system (referred to as “the L” by locals), getting around town is convenient and affordable. Visitors can also quickly tap their way through apps like Uber and Lyft for personalized pick-ups and drop-offs. For those wanting to pre-burn calories in anticipation of indulging in deep-dish pizza or Chicago-style hot dogs, Divvy offers more than 580 bike share stations throughout the city.

Summer Sizzles

Chicago’s cultural calendar overflows throughout the year, but things really heat up in the summer with these annual signature events, providing a terrific anchor for a weekend getaway.

Chicago Pride Fest and Parade (June, 2019) – Mark your calendars for these back-to-back LGBTQ celebrations. Chicago Pride Fest (June 22-23) is a two-day festival the weekend before the actual parade on June 30, which marks its 50th anniversary.

Lollapalooza (August 2-5) – More than 170 acts descend upon eight outdoor stages for this mega-musical festival that dates back to 1991. Attendees get just as excited about the “Chow Town” food offerings, art market and merchandise.

Northalsted Market Days (August 10-11, 2019) – Boystown becomes a thriving street festival each August, packed with live music on four stages, more than 200 vendors, and plenty of rainbow pride.

Reeling: The Chicago LGBTQ+ International Film Festival (September 19-29, 2019) – The festival dates back to 1981 and is the second-largest of its kind, including features, shorts and special appearances by the filmmakers.

Curtain Up

Arts lovers can hit a home run in Chicago, even if they’re not at Wrigley Field. This year shines a spotlight on live performance as the city declares 2019 The Year of Chicago Theatre. From Broadway musicals to storefront theaters producing new works, LGBTQ stories have a home in Chicago.

Pride Film & Plays – Located in the Pride Arts Center, the theater company produces works with LGBTQ characters and themes.

About Face Theatre – In its 20-year history, the boundary-pushing company has produced more than 60 productions exploring the narrative of the LGBTQ community.

Broadway in Chicago – Broadway’s best can be found in Chicago (and is often more affordable than its New York City counterpart). Pre-Broadway runs and national tours can be seen at five distinctly gorgeous venues throughout the city.

Mark Your Calendar:

Desire in a Tinier House (May 30 – June 29, 2019) – A world premiere about the challenges of maintaining a gay relationship in today’s culture. (Pride Film & Plays).

Falsettos (May 28 – June 9, 2019) – William Finn and James Lapine’s Tony Award-winning musical about an unconventional family at the beginning of the AIDS crisis. (James M. Nederlander Theatre).

Stay a While

From affordable to luxurious, hotel accommodations run the gamut and suit every style and budget. Here are three distinct picks to consider:

Hotel Lincoln – Steps from Lincoln Park Zoo, this boutique property features a rooftop bar and tons of quirky design touches.

Hotel Zachary – Wrigley Field architect Zachary Taylor Davis inspired this recently opened Marriott property (use those points!), which resides within a pitch of the famed baseball stadium and neighboring Boystown.

The Langham Chicago – Modern luxury reigns supreme at this stylish hotel located within an iconic Mies Van der Rohe landmark building.

ACME Hotel Company

The ACME is loaded with character and artsy touches, hipster vibes, and a super friendly staff. The chalkboards on the doors allow everyone to represent their true selves. But it’s really the location that’s paramount here: steps from The Loop, the mall, and the famous UNO’s.

Where to Eat

Wells Street Market – The newly opened food hall in the Loop offers something for everyone. Favorite bite: Furious Spoon’s shoyu ramen.

Bavette’s Steakhouse – Honoring Chicago’s long tradition as a steakhouse town, this swanky spot offers French flair and romantic enclaves for the ultimate date. Favorite bite: Chicago cut classic ribeye with béarnaise.

Southport Grocery and Cafe – Baked-from-scratch pastries and all-day breakfast can be found along with ancho chili-infused Bloody Mary’s at this Lakeview neighborhood spot. Favorite bite: grown-up pop tart with preserves and mascarpone.

Hot “G” Dog – Along with Chicago-style pizza, hot dogs are a Chicago staple. These artisan (and budget-friendly) options are a favorite among locals. Favorite bite: Chicago dog with a side of duck fat fries (weekends only).

From Dusk ‘til Dawn

Overwhelmed by so many amazing choices? Here’s an itinerary to jumpstart your weekend:


Head to Sidetrack, the legendary Boystown video bar that has been the city’s go-to LGBTQ destination since 1982. Extend your getaway by a day to stay for Musical Monday, a standing ovation-worthy tradition.

A drink at Little Jim’s Tavern, the city’s first gay bar, is also essential. The bar has tons of old-school charm, local gays and daily drinks specials. And as far as legendary bars go, no pub crawl is complete without an Uber to Andersonville for some lesbian karaoke at Spyners Pub. By now, you’re plenty drunk enough to belt out some Journey.


The Legacy Walk, located in Lakeview, features 37 bronze memorial markers and interactive technology to connect with the people and places that have been instrumental in the nation’s LGBTQ movement. Check out the historic stroll during the day before heading to The Art Institute of Chicago for some of the country’s most stellar art. Be sure to visit the incredible 68 Thorne miniature rooms.

Come nightfall, head uptown to explore the city’s diverse collection of bars. Big Chicks is a friendly, low-key vibe that can be found Uptown with a different energy than Boystown bars. For the high-energy millennial crowd, Hydrate is a high-energy club with a stellar roster of DJs including former “RuPaul’s Drag Race” contestant Nina Flowers. Also pop into Berlin, a “pan-cultural” late-night dance club open ‘til 4 a.m.


Drag reigns supreme at the Kit Kat Lounge & Supper Club, a terrific spot for brunch (prix-fixe menu plus a la carte) and entertainment.

More gay-friendly Illinois:

This is just one of our many favorite stories and hotspots to help you discover gay-friendly Illinois for yourself. Continue your exploration here.

Enjoy a more immersive Illinois experience in the magazine:

ManAboutWorld is an app-based travel magazine by gay men which provides travel inspiration and trip-planning information for all whether you’re in the LGBTQ+ community or are an ally. It’s built exclusively for mobile devices and is not available in print. We first published these articles in the spring 2019 issue and make them available here for your enjoyment. The app and issues are all free. Download it for Apple devices or Android devices.

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