Chicago's LGBTQ Neighborhoods: Andersonville

Where to eat, stay, shop, and play in one of the largest LGBTQ communities in Chicago.

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By Amber Holst of Concierge Preferred

Home to one of Chicago's largest gay and lesbian communities, Anderson is recognized for its diversity and a quirky atmosphere. The neighborhood is made up of many locally-owned businesses and stylish boutiques. Here's your guide to the best of the neighborhood, just in time for Pride Weekend.

Where to Eat

Big Jones

Every Saturday and Sunday, this sustainably-sourced restaurant in the Andersonville neighborhood serves up Southern heirloom-style brunch dishes, such as sweet potato pancakes, gumbo ya-ya, Andouille and corn griddle cakes.

The Hopleaf Bar

This Belgian-inspired kitchen and bar is the spot for mussels, house-made sausages, charcuterie and an extensive lineup of specialty imported beers, ciders and wines. This venue is ages 21 and over, and a private party room is available for large groups. 


Like any good trattoria, Anteprima rotates much of the menu according to season, but housemade pastas prove as perfect with pancetta ragù in cold weather as they do with bright fava beans and ricotta in spring. The real draw here in summer, though, is romantic and secluded back patio. It’s a neighborhood must-do.

Where to Shop

Andersonville Galleria

If you're looking for a quirky and cool gift or something special for yourself, this is your go-to shop. This multi-level retail space is filled with art, jewelry, clothing, and gourmet food items—many of which are made by local Chicagoans— so you're definitely not leaving empty-handed.


This quaint shop offers an assortment of prints, stationery, gifts, and novelty items. They will also do custom framing of your photos of all sizes. We love their wonderful collection of unique and quirky gift ideas that are perfect for locals and visitors alike. 

Alley Cat Comics

Snake your way down a gangway off of Clark Street and into AlleyCat Comics. Andersonville’s must-visit for all things illustrated this shop also boasts a healthy children’s’ section that includes graphic novels, single issues, trade paperbacks, magazines and family board games.

In Fine Spirits

Oenophiles and amateurs alike should feel at home in this Andersonville shop, where the staff always seems to come through with surefire, affordable suggestions and where the focus is on under-the-radar varietals and limited-release, Midwest-centric craft brews and spirits.

Swedish American Museum Shop

An anchor of this once predominately Swedish neighborhood, pop into their gift shop for a fun souvenir.  Here you’ll find Swedish dishcloths, classic wooden Dala horses, and imported treats. For the littles, pick up a stuffed Dala Horse and a Daim chocolate bar. 

Women & Children First

This independent bookstore bills itself as one of the largest feminist bookstores in the country. Its cozy stacks are home to more than 30,000 volumes, with a heavy focus on books by and about women, children's books for all ages, and the best LGBTQ fiction and non-fiction available.

Where to Play

Replay Andersonville

The Andersonville outpost of the Boystown beer-and-bourbon barcade adds food to the mix, with burgers, brunch and more to fuel your retro gaming. The extensive beer list and even bigger collection of bourbons are the reasons to visit, other than the nostalgia of playing Donkey Kong and Joust.

Simon’s Tavern

An Andersonville nightlife mainstay, this is one of the few places in Chicago that serves glog (and stays true to the neighborhood’s cultural roots). They boast a solid selection of beers on tap and more than 25 in bottles. Complete with hunting-inspired murals on the wall—and even some Viking paraphernalia—it’s a neighborhood bucket-list bar you’d be remiss not to check out. 

Marty’s Martini Bar

As one would expect given its name, Marty’s eponymous drink arrives filled to the brim (and strong). The signature cocktails here are served in inventive varieties that include chocolate hazelnut and strawberry shortcake martinis. For those looking for something lighter, they also offer beer and wine by the glass. 

What to See

Swedish American Museum

A fixture in the neighborhood for over 40 years, this 24,000 square-foot cultural museum features two gallery spaces with special art exhibits, “The Dream of America” exhibit, the Brunk Children’s Museum of Immigration, a genealogy center, and a Museum Store. 

Where to Stay

The Guesthouse Hotel

Let this be your charming base for exploring Andersonville or the North Side. Each room is a two- or three-bedroom suite with a kitchen (stocked with cookware and glasses), a balcony with a grill and a washer and dryer. While the hotel is located within a few blocks of excellent restaurants and bars, you can also have ingredients delivered if you want to cook in the kitchen. Get more info on The Guesthouse Hotel

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