The insider’s guide on where to party, stay, shop, and eat in Chicago
Get the inside scoop on Chicago’s LGBTQ+ culture. From bar-hopping tips to hidden gems, explore the city like a local with this guide.
Ian Helms, the Director of Growth Marketing at Q.Digital, GayCities‘ parent company, is a proud Chicagoan, coming up on a decade in the Windy City. Having always lived in and around Boystown—now known as Northalsted—he and their partner, Smith, recently bought a condo in the heart of the gayborhood.
With his deep connection to the area and active involvement in the LGBTQ+ community, Ian makes the perfect guide for where to go, what to do, and how to make the most of Chicago’s vibrant queer nightlife.
(@ianhelms)GayCities chatted with Ian to get his insider take on everything from the best bars to the tastiest spots in Chicago. Let’s dive into their recommendations below.
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Where do you bar hop in Chicago when you go out with your friends, and in what order?
My grandparents used to own a tavern in Wisconsin, and I think that’s why we’ve always preferred divier bars—they just feel comfortable and familiar to me. Plus, they usually have cheap drinks, which often lead us to dancing (something my partner, Smith, is always up for).
Where we go really depends on the day—I honestly usually follow the drink specials. We’ll pretty much always start at Sidetrack before making a quick loop south to check out Splash or Scarlet for the vibe and lines. Then, we’ll head to Roscoe’s Tavern if there’s no cover, and maybe Bobby Love’s after that. If we’re staying out super late, we usually end the night at Charlie’s.
As a bonus, the walk to Bobby Love’s passes a bunch of other bars, so we keep things spontaneous if something else catches our eye along the way.
I’d be remiss not to shout out Andersonville, though. We usually hit SoFo Tap, Meeting House Tavern, and Atmosphere—in that order or reversed, depending on which side of the neighborhood we start on. Atmosphere does typically get busier and dancier later, though. There’s also Max’s Place, a super queer-friendly dive bar that’s recently under new ownership.
Which gay bar is your favorite?
In Northalsted, Sidetrack is almost always a must. It’s huge, with tons of rooms offering different vibes, including a rooftop, and it never has a cover. They’ve got theme nights, trivia, drag shows—basically anything a gay bar could offer, all in one place.
The drinks are strong, but they’ve also got great non-alcoholic options if that’s more your speed. The music varies throughout the different bar areas and is always on point—whether it’s pop divas, the latest music videos, or even Broadway show tunes a couple of nights a week. It’s a guaranteed good time.
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It’s thanks to gay bars like Sidetrack and neighboring Closet and Roscoe’s Tavern for bringing Chicago’s gayborhood to fruition.
Who is the best drag queen in the city?
This is honestly such a hard question because the drag scene here is so lively and diverse! Without defaulting to some of the RuPaul’s Drag Race queens, one of the first names that comes to mind is Lucy Stoole—she’s literally the hostess with the mostest and is always at the best events in town.
She recently hosted Drag Night Chicago with queens from Drag PAC in conjunction with the 2024 Democratic National Convention, and hosts lots of other celebrity-packed events around the city every month.
On the flip side, Tenderoni is hands-down my favorite drag king. He’s got the whole package: talent, fashion, dance moves, advocacy—all the things that make for an amazing drag performer.
For a better taste of Chicago’s drag scene, check out my list of Chicago drag queens and kings on Queerty.
Which hotel do you suggest for out-of-town friends?
Hotel Versey Days Inn by Wyndham Chicago is a little south of Northalsted, but it’s walkable, with pretty solid rates (by Chicago standards). Best Western Plus Hawthorne Terrace Hotel is also right off Halsted Street with a gorgeous courtyard and recently renovated rooms that get great reviews. Both are super accessible for exploring the area.
What is your favorite food, and where do you get it in Chicago?
This really depends on my mood and the vibe. I love to cook, so I don’t eat out often, but Asian cuisines are ones I didn’t grow up with and don’t really know how to make well at home.
Pho’s Thai Cuisine is a hole-in-the-wall BYOB spot that Smith and I eat at the most—they’ve got a spice scale you order from and a photo wall for those who go off the chart. Otherwise, Taqueria Tejupilco is a great no-frills Mexican spot that recently opened.
For a nice date night, Pingpong has fantastic Asian fusion food and cocktails, or AMORE Sushi House is also a fave.
If we’re out super late, Willie’s is an 18+ spot with a fun menu and vibe.
All these places offer plant-based/vegan options too, which is key for us.
Where do you like to go shopping in Chicago?
Mostly online. As a pocket gay, I struggle to find clothes that fit at most “normal” stores, and since we don’t have a car, it’s easier to shop online for other things, too.
But when I’m in the mood, Broadway (one block east of Halsted Street) is my go-to for shopping. Unabridged Bookstore is an LGBTQ+-owned bookstore that’s been around since 1980—it’s always a good stop. There’s also Plant Stand Collective next door, which is Latina-owned, and our living room has quite a few plants from there.
Sway is a new Black-, Latino-, veteran-, and queer-owned cannabis shop in the center of Northalsted where Town Hall Pub used to be. It’s super welcoming and way less intimidating than its bigger competitors in the area.
And while I try to keep my shopping in check, a decent chunk of my monthly budget goes to Solidcore, which is essentially a strength Pilates class.
The Boystown studio is incredibly LGBTQ+ friendly, with LGBTQ+ coaches and special Pride themes throughout the year. It also has a solid amount of queer and male clients, which makes it feel even more welcoming. It’s become my go-to for staying fit.
What’s the best part about the nightlife in Chicago?
Smith and I both agree that the best part of Chicago’s nightlife is how walkable it is. You can pick a neighborhood, settle into its vibe for the night, and mosey between bars without needing to hop in a car or on a train.
There’s always something happening every night of the week, so you can immerse yourself in the community whenever and however you’d like.
From drag shows that showcase the city’s talent and diversity to unique shopping spots, and cozy restaurants serving some of the best food in town, Chicago truly offers something for everyone—whether you’re visiting for the weekend or staying for a lifetime.
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