Discovering Andersonville, one of Chicago's coolest neighbourhoods

Touted as one of Chicago's coolest areas, Andersonville's community-focused businesses and progressive values are drawing in travellers keen to connect.

View over the neighbourhood of Andersonville, looking south towards the centre of Chicago.

Photograph by Andersonville Chamber of Commerce
By Josephine Price
Published 16 Feb 2023, 12:00 GMT

“It’s the story of Chicago, you know,” says Lesley Martinez, laying down some history ahead of our tour. “The city started out as a patchwork of ethnic enclaves.” I’m with the community organiser in the northerly neighbourhood of Andersonville, one of those historical cultural areas. Originally a Swedish settlement, it was named after the Anderson family, who arrived here in the 19th century.  

But its Scandinavian roots aren’t what’s putting the area on the map for travellers. In recent decades, the area has become a bastion for liberal rights and social inclusivity, with an exciting array of community-focused, LGBTQ+ friendly venues to explore. The Windy City has had a far-reaching impact on US culture, of course, from art deco architecture and blues music to its famous deep-dish pizza. But this little neighbourhood might yet become one of its most impactful achievements.   

We’re sitting in one of Andersonville’s many family-owned restaurants ingesting bowls of fiery fried-tofu rice and drinking light, citrussy beer. It’s fuel for the afternoon tour that Lesley — who grew up here and works for the local chamber of commerce — has offered to host. Our table, in front of a vast window, showcases the neighbourhood’s  
sun-drenched main corridor, North Clark Street. Electric and eclectic, the street is slung out in a low–rise collection of brick buildings. It’s a centre of commerce, but also of community get-togethers. 

As we head out to explore, Lesley tells me the street often comes alive with festivals — more than 19 live events take place here every year. Midsommarfest in June is the highlight, when the area’s Swedish heritage combines with the jubilant atmosphere of Pride month to create an unforgettable street party, bringing together different elements of society. “We have a lot of fun!” says Lesley. “And this year it’s all about coming back together, centring on community and promoting diversity.”  

She leads me into the Brown Elephant, a former playhouse turned vintage resale shop. It’s unassuming from the outside, but inside I discover a cavernous paradise for thrifters. I rifle through the rails of colourful vintage shirts and wander through the maze of furniture, amid the peeling grandeur of what was once the Calo Theatre. A giant Pride flag hangs above the old stage.  

Thrift stores give a glimpse into what a local people have previously loved, but this one works hard to cultivate love within the present-day community, too. Lesley explains the shop’s outreach mission: the venue is also home to a free HIV and STI screening centre. What’s more, all profits from vintage sales go towards LGBTQ+ healthcare, to fund the uninsured and underinsured. It’s important work — the area has a large gay population and a particularly strong concentration of lesbian bars, which led to Andersonville’s informal moniker, ‘Girlstown’. 

Next, the Women & Children First bookshop lures us in with its eye-catching purple awning and a playful hybrid banner in the window combining the rainbow flag with that of the city of Chicago. Founded elsewhere in the city in 1979 as an independent feminist bookshop, it relocated to Andersonville in 1990 to ride the progressive waves that were rippling through the area. The community notice board profiles queer open-mic nights, abortion rights demonstrations and local podcasts. “The bookstore has really been a safe space for mobilisation and conversation,” Lesley tells me. “It’s an anchor of our community.”  

We find another of these anchors further along North Clark Street: the huge Life at the Intersections mural by queer and non-binary artist Molly Costello. Colourful characters pop against a navy backdrop; some figures are tending plants while others are scrawling ‘Protect trans youth’ on a wall or marching with Pride flags. Molly created this piece in July 2021 after interviewing 77 local residents about their lived experiences. It’s an artwork that represents, as Molly’s website puts it, “visions of a future of Andersonville that continues to challenge white, cis, heteronormative atmospheres”.  

“We want our neighbourhood to be an inclusive place,” says Lesley, proudly. “We’re leading the conversation on centring Black trans lives, the most marginalised community in the city of Chicago.” ‘Black Trans Lives Matter’ is scrawled across the wall on the next street corner I pass by.

Walking down North Clark Street, Andersonville's main thoroughfare.

Walking down North Clark Street, Andersonville's main thoroughfare.

Photograph by Andersonville Chamber of Commerce

As well as having a reputation as a hub of progressive social activism, Andersonville is known for its independent shops: you can visit 300 businesses in a 1.5-mile radius. I whirl through the highlights with Lesley. We browse Rattleback Records for vinyl; Scout for funky furniture; and Raygun for slogan tees with quirky messages such as ‘America Needs Lesbian Farmers’. Veering off North Clark Street, we check out Nobody’s Darling, a queer, Black-female-owned bar making killer cocktails. It’s named after the evocative 1973 Alice Walker poem of the same name, which is a tribute to outsiders and outcasts. It feels like a fitting place for my time with Lesley to draw to an end.  

Andersonville is by no means an untapped discovery of mine. In 2021, the area was listed as the second coolest neighbourhood in the world by Time Out, narrowly beaten to the top spot by Copenhagen’s Nørrebro. This district has attracted wandering souls since the Swedes arrived in the 19th century. And for travellers in 2023, it offers a more intimate base to the north of the sights of downtown Chicago.  

Lesley describes her home as having the makings of utopia. It’s a community working to provide for residents based on agreed tenets: diversity, inclusivity, safety, mutual support and care. Her enthusiasm for the ongoing project is contagious. “We’re fighting the cookie-cutter neighbourhood experience,” she tells me, as we say goodbye. “It’s very unique here. From a big city perspective, it really has that small-town feel.”

How to do it

American Airlines, British Airways and United Airlines all fly direct from London Heathrow to Chicago. Canopy by Hilton Chicago Central Loop has rooms from $164 (£136), room only.

More info

Left: Top:

The neon signage of the non-denominational Philadelphia Church on North Clark Street.

Photograph by Andersonville Chamber of Commerce
Right: Bottom:

Community noticeboard at the Women & Children First bookstore.

Photograph by Josephine Price

Four more Chicago neighbourhoods to explore

Best for Mexican food and queer art: Pilsen 
Settled by Czech immigrants and now home to the largest Mexican-American community in the Midwest, Pilsen is known for bright street art that foregrounds anti-deportation and gay pride slogans. Shop at Mestiza for Mexican arts and crafts with feminist and LGBTQ+ messaging, and visit the nonprofit Woman Made gallery promoting female-identifying artists. Elsewhere, don’t miss the ice cream at La Michoacana and check out the Lo Rez microbrewery.

Best for Puerto Rican heritage: Humboldt Park 
Puerto Rican flags adorn the streets around the green space that gives the neighbourhood its name; the area has been home to an expat community since the 1960s. It’s a particularly jubilant district, with locals playing street-side games and drivers often blasting out Latin music in the summer sunshine. Join the Paseo Boricua Tour Company for walking tours and expert insights into the heritage of the neighbourhood, taking in more than 70 murals and 20 eateries celebrating the best cuisine in this part of the city.

Best for fine dining and live blues: Lincoln Park 
This affluent area draws in a culinary crowd looking for a good time. Situated near the eponymous Lincoln Park (the largest public park in Chicago), this neighbourhood revolves around North Halstead Street and its tributaries. Try Parson’s Chicken & Fish for a frozen negroni; sample the extensive tasting menu at Galit, a homage to Middle Eastern cuisine; and end your evening at Kingston Mines for live blues across two stages.

Best for independent shops: Wicker Park and Bucktown 
These two neighbourhoods sit side by side, and their small, locally owned businesses are best explored in tandem. Peruse vinyl and check out local gig listings at Reckless Records; go wild for beautiful stationery at Topdrawer; ingest freshly fried falafel at Sultan’s or plant-based cooking at Bloom; and discover new styles at clothing shop Una Mae’s. Then stretch your legs on the Highline-style 606 trail.

Published in the US Cities guide, distributed with the March 2023 issue of National Geographic Traveller (UK) 

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