Chicago

Everything That Makes Chicago a Great Summer Destination for LGBTQ Travelers

Gay nabes like Andersonville are just the starting point.

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Chicago, like most major cities, normally attracts millions of tourists throughout the year with its incredible culture, architecture, live entertainment — not to mention a stunningly beautiful lakefront that beckons people to run, bike, and host barbecues. Now that the world has started to come back to life, Chicago is throwing open her arms to visitors once again this summer. As a lifelong Chicagoan, and someone who loves exploring the city, it has brought me so much joy to feel every neighborhood reenergize and seeing restaurants, which have suffered painfully over the last year, get packed again.

The approach of summer means we’re on the verge of gathering once again for Chicago’s famous street festivals, including Market Days and Pride Fest (later in the year). I, for one, can’t wait to be back outside, among others, celebrating with my LGBTQ family and our allies as I have for years. For me, it’s about being able to be myself, in my city, with so many others who feel the same. And that’s one reason I love Chicago as much as I do. I get to be my true self every day, because this city really does welcome all the colors of the rainbow. 

When you visit Chicago, requisite jaunts to the gay nabes of Andersonville and Northalsted (which locals still know as Boystown, officially renamed last year) can’t get overlooked. But depending on how much time you have to spend here, Chicago has so much to offer. The city comprises 77 distinct neighborhoods with sub-neighborhoods within (like Andersonville, which is Edgewater). To think you need to spend all your time in one place is to narrow the possibilities of soaking in all that Chicago offers. Here’s everything you need to do to connect with the city’s LGBTQ community and beyond while you’re here.

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There’s a wide range of culture, from the Art Institute to the Leather Museum

It’s no understatement that Chicago claims some of the world’s greatest museums. Absorb classic and modern works at the Art Institute, for current exhibits from Bisa Butler and Monet, but also permanent works like American Gothic and Nighthawks, in the main building and the adjacent Modern Wing. Visit the Museum of Contemporary Art, where you’ll often find works by LGBTQ and BIPOC artists. Learn about Chicago’s history as a global center for architecture and design at the Chicago Architecture Center — or simply grab a coffee and ride the Brown Line around the heart of the Loop to see many famous skyscrapers. 

The WNDR Museum's ever-evolving immersive exhibits meld art and technology. Learn about Mexican culture in Pilsen by curating your own walking tour of the vibrant murals throughout this South Side neighborhood and continue down to Washington Park to the DuSable Museum of African American History, celebrating its 60th anniversary in 2021. If leather and kink are your thing, don’t skip the Leather Archives & Museum in Rogers Park. And the Legacy Walk along Boystown's North Halsted strip honors LGBTQ history — just look for all the towering rainbow pylons that showcase plaques of LGBTQ pioneers and their stories.

You can support LGBTQ businesses while you shop around the city

Chicago has phenomenal shopping, especially along the Southport Corridor in Lakeview and Milwaukee and Damen Avenues in Wicker Park/Bucktown. But if you want to keep it in the family, the city has wonderful LGBTQ-owned businesses to invest your money. Andersonville features a number of vintage shops like Scout, for reclaimed objects and refurbished mid-century pieces; Mercantile M for affordable finds that add pops of color to your life; and Roost, for that gorgeous barware set or signature piece for your bedroom. When you want a book — whether a New York Times bestseller or a piece on LGBTQ history — both Women & Children First and Unabridged Bookstore hold iconic status as two of the best booksellers in the city. 

Don’t fret when you realize you forgot that cute shirt you wanted to wear out to the bars. Both CRAM and Cowboys and Astronauts have hip fashion and accessories — and C&A also has wonderful candles, body products, bags, and more. Need a gift? Asrai Garden features a beautifully curated collection of wares from vases to jewelry to apothecary, while Foursided has all your games, cards, candles, and more whimsy. Don’t even think of showing up to that party you got invited to empty handed; Provisions has you covered for wine, spirits, and, of course, cured meats and cheese. 

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Whether you’re dreaming of visiting Chicago, a tropical locale, or a far-flung city, it starts with making a plan. As an active ally to the LGBTQ community, Orbitz has great tools for LGBTQ travelers to research, book, and feel welcomed wherever they travel — like curated hotel listings for properties that have taken their inclusivity pledge. All you have to do is decide what you’re going to do when you get there.

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The city truly lights up for Pride

As the capital of the Midwest, Chicago turns it out throughout June each year for Pride — and it’s not to be missed. While the annual Pride Parade the last weekend in June has welcomed upwards of 1 million revelers to show their truest colors, this year’s festivities remain up in the air — as do those for the Pride Fest street fair. Normally that happens the weekend before the parade, but organizers now say it may occur in September. That said, we can all get our pride on at Pride in the Park. The outdoor festival held in Grant Park with international musical acts and more drag queens than RuPaul can toss shade at will officially take place June 26-27. 

To keep the celebrations going beyond June, Chicago Black Pride runs July 1-5 with various events taking place around the city, including the Inn of Chicago, Metro, and Fantasy Nightclub. The annual Chicago Dyke March, a “grassroots mobilization and celebration of dyke, queer, bisexual, and transgender resilience,” will hopefully take place in Little Village, but official plans have not been announced. And while the International Mr. Leather competition usually draws leather-clad men every Memorial Day weekend, for 2021 it’s been moved to November. Now you have a reason to come back in the fall.  

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There’s so much more to eat than deep dish pizza

Chicago has long bucked its dated reputation as a meat and potatoes town, where you can get a hot dog “dragged through the garden,” or feast on deep dish pizza. Sure, you can still have all of that, but there’s so much more. The city has 24 Michelin starred restaurants like world-renowned Alinea, the elegant yet playful Ever, culinary brewpub Moody Tongue, sushi star Mako, and seafood-driven Porto. And while the Fulton Market District hosts some of the city’s hottest restaurants like newcomer Rose Mary (coastal Adriatic) and celeb chef Stephanie Izard’s Girl & The Goat, you’ll find creative menus to sate your appetite all over town. Hit Testaccio in Logan Square for Roman fare; Big Star in Wicker Park or Wrigleyville for tacos, tequila and shots of whiskey; Hyde Park’s Virtue for a true taste of Southern fare; or Anteprima in Andersonville for classic Italian. 

Of course, you can support wonderful LGBTQ-owned spots including Split Rail for some of the city’s best crunchy hormone-free fried chicken; Big Jones for Southern heritage fare (and a damn good brunch); seasonal American and handcrafted cocktails at Wood; and Uptown’s Tweet, where owner Michelle Fire welcomes you with open arms to enjoy the best organic-focused breakfast in town. Stick around long enough and you can roll into Fire’s adjacent Big Chicks bar, where the dance floor gets hot every weekend and the back patio lets you chill all summer. 

Speaking of patios, the roof at Boystown’s Sidetrack is the best place to sip a boozy slushie before meandering through the massive bar’s numerous rooms. Then pop next door to dance at Progress or across the street at Roscoe’s, where you’ll likely see some Drag Race stars. Looking for some ladies? The Closet is one of Chicago’s oldest LGBTQ bars for laid-back drinks and a late-night dance. Or head to Andersonville’s Joie de Vine, an intimate lesbian-owned neighborhood wine bar. And when you really just need to dance, Sunday nights at Queen! at Smart Bar, might be the sexiest house music-driven queer party in town.

The live entertainment scene is legendary

While theaters have been dark throughout the pandemic, with news of Chicago gearing up to fully re-open, that includes live entertainment of all kinds. The city has a diverse theater scene and is known for its neighborhood theater companies like Theater Wit, Black Ensemble Theater, Steppenwolf, About Face Theatre, and Court Theater. Want to go big? Broadway in Chicago is the next best thing to the Great White Way with upcoming musicals including “Six,” “The Devil Wears Prada,” and “Moulin Rouge! The Musical.” And don’t get us started on all the live music you can take in any night of the week. Iconic music venues like Metro, Schubas Tavern, Lincoln Hall, Thalia Hall, Buddy Guy’s Legends, Green Mill Cocktail Lounge, and countless others around the city showcase rock, hip-hop, jazz, blues, and EDM. Just bring your earplugs.

No matter if you have a couple of days or a full week, your visit to Chicago can feature everything you want — from dancing the night away, to enjoying a fantastic meal, to simply whiling away a few hours having a kiki at the very gay-leaning Hollywood Beach, where you can ogle an array of queerness or get lost in a book. However you do Chicago, Chicago will do you right back.

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