Chicago’s coolest neighbourhoods

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. mestizashop.com womanmade.org lamichoacanapremiumpilsen. com lorezbrewing.com

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. nmprac.org paseoboricuatours.com

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. parsonschickenandfish.com galitrestaurant.com kingstonmines.com

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. reckless.com topdrawershop.com chicagofalafel.com unamaeschicago.com