Chicago has opened her arms — wide — to the LGBTQ community. While our presence is seen and felt all over the city, there’s no question that Boystown and Andersonville continue to stake claim as the epicenter of social life in Chicago — call them GayHQ if you will.
From great restaurants and lively bars to cute boutiques and energetic festivals, both Boystown, located in East Lakeview not far from Wrigley Field, and Andersonville, a little farther north and about a mile west of Hollywood Beach, have plenty to offer residents and visitors.
Each also has quaint boutique hotels and guesthouses — so you’re never far from all the action.
1. Everyone Loves a Street Fest…
Market Days (Aug 12-13, 2017)
Touted as the Midwest’s largest street festival, the annual Northalsted Market Days — celebrating its 36th year in 2017 — looms even larger when it comes to live music (this year’s acts include Jody Watley, Cece Peniston and hot out musician Steve Grand), dancing to DJs spinning in the street and all the corn dogs you could ever hope to devour.
Taste of Andersonville (Aug. 9, 2017)
This Far North Side enclave has become a dining destination to reckon with and during the annual Taste of Andersonville, you can sample from upwards of 20 restaurants that in the past have included Elixir, Jerry’s, Appellation, Lady Gregory’s and Vincent not to mention tastes of locally made bourbon, rye and gin from Koval Distillery.
Lakeview East Festival of the Arts (Sept. 9-10)
Don’t miss this daytime art walk along Broadway where more than 150 painters, sculptors, photographers, jewelry makers and other artists display their wares — and everything is for sale. This family-friendly event has plenty of food, live music and other activities.
Halloween (Oct. 31, 2017)
One of Boystown’s biggest parties for more than 20 years, the annual Halloween parade brings out the most creative and over-the-top costumes strutting down Halsted Street.
2) Hungry? Don’t miss these restaurants while checking out the festivals.
Wood: Whether for dinner or weekend brunch, Wood does it right when it comes to local and seasonal share plates like salmon crudo with green papaya salad; tagliatelle with smoked pork shoulder; and Berkshire pork carnitas in a mole rojo. Oh, and did we mention the super hot bartenders mixing super strong cocktails?
Chicago Diner: Vegans and vegetarians have flocked here for more than 30 years for meat-free deliciousness.
HB Home Bistro: Date night doesn’t get better than this rustic, BYOB spot with an often-changing menu. Don’t miss the PEI mussels with chorizo and truffle fries.
Wakamono: When you want super-fresh sushi done in both traditional and inventive preparations — and great eye candy at all the tables — head here.
Anteprima: This quaint trattoria with a beautiful back patio has a menu featuring seasonal market finds, manageable plates of pasta, whole roasted fish and a fantastic Italian wine list.
Lady Gregory’s: When you want a hearty meal with stacked and elevated Irish pub fare like country chicken pot pie; lobster mac and cheese; and fish and chips (don’t worry, they have salads, too) in a cozy yet bustling atmosphere, you will never go wrong at Lady Gregory’s.
Big Jones: Heritage Southern fare with one of Chicago’s best bourbon collections? Yes please!
Hamburger Mary’s: Burgers and beers served with a side of sass is definitely on order — and when you’re done, pop up to Mary’s Attic to dance it all off.
3. Ready to bar hop before and after the festivals?
When you’re looking for a little craziness with a mix of everything, head to Boystown. When you want more of the same with a little more mature crowd, make Andersonville your destination.
Sidetrack: The Grande Dame of Halsted, Sidetrack is one of Chicago’s largest and longest-running gay bars. With multiple rooms, bars and a rooftop — along with sing-along show tunes and comedy nights — this video bar always has something going on.
Elixir: This proper cocktail bar has locations in Boystown and Andersonville, so whenever you’re craving a craft cocktail, it’s never far out of reach.
Replay: Video games galore line this bar and you can get your fun on in both neighborhoods. When you need a break from the joystick, head out back to the Boystown location’s sprawling patio.
Marty’s Martini Bar: A staple of Andersonville’s Clark Street corridor, Marty’s makes some of Chicago’s strongest martinis — and beware, they come in two sizes: large and larger.
4. And now let’s shop …
CRAM: Whether you’re looking for cute new shorts and sneakers or a hot tank and box cut swimsuit for the beach, CRAM has a great mix of forward fashion and circuit party chic.
Unabridged Bookstore: This longtime Boystown staple harks back to the days of pre-Amazon bookshops where a super knowledgeable and friendly staff help you pick out your next beach read, find a travel guide or show you its vast selection of LGBT reads.
Beatnix: When you need a costume for the festival or the airline lost your bag with all your wigs, Beatnix is your one-stop shop for all things dress up.
T-Shirt Deli: Fun, custom T-shirts is the name of the game here. Whether you want to pick from one of their designs or make your own, you’ll leave with an original.
Scout and Roost: Big fan of antiquing? No need to visit Amish country. These two shops — one at each end of Clark Street — have some of the best finds from vintage glasses to refurbished bookcases and so much more.
Notre: From Adidas and A.P.C to Y-3 and Yeezy, Notre has fashions for the most fashion forward among us.
For more reasons to enjoy great festival trip to Chicago, check out the video: