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Beyond the Loop: Chicago’s Backstreets, Murals and Sunday Markets

Chicago, United StatesFebruary 15, 20252 min read
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A classic Chicago-style hot dog - poppy-seed bun, tomato wedges and a whole dill pickle spear - resting on its paper wrapper01
A classic Chicago-style hot dog - poppy-seed bun, tomato wedges and a whole dill pickle spear - resting on its paper wrapperPhoto: Daniel Romero / Unsplash

A mural-covered Mexican neighbourhood, a Vietnamese high street, a Victorian glasshouse and an elevated railway turned garden path. The Chicago past the skyline.

Chicago's downtown is a museum of architecture, and it deserves the attention it gets. But the city is really seventy-seven neighbourhoods stitched onto a grid, and the ones off the tourist map are where the murals, markets and immigrant kitchens are. Take the "L" a few stops further than you planned.

Key facts

  • The grid: street numbers radiate from the corner of State and Madison, which makes navigation unusually forgiving.
  • Getting there: the "L" reaches most of these neighbourhoods; a day pass makes wandering cheap.
  • Seasonality: outdoor markets run roughly May to October, with reduced indoor versions in winter. Check dates before travelling.
  • Free entry: several of the best small museums and gardens here cost nothing.

Pilsen

The heart of Mexican Chicago, and the most visually alive neighbourhood in the city: block after block of murals, mosaic-fronted buildings and painted shutters along 16th Street and beyond. The National Museum of Mexican Art holds one of the country's largest Mexican art collections and charges no admission. Eat at a taqueria; the standard is high and the prices are not.

The Chicago skyline low on the horizon across the turquoise water of Lake Michigan
The Chicago skyline low on the horizon across the turquoise water of Lake MichiganPhoto: Muzammil Soorma / Unsplash

Argyle Street and Devon Avenue

Two immigrant high streets on opposite ends of the north side. Argyle Street in Uptown is Vietnamese and Cambodian: pho counters, bakeries, herbs on the pavement. Devon Avenue runs through South Asian Chicago, with sari shops, sweet shops and some of the best regional Indian and Pakistani cooking in the Midwest.

Garfield Park Conservatory

One of the largest conservatories in the United States, designed by landscape architect Jens Jensen to look like a landscape rather than a greenhouse. The fern room is a prehistoric daydream in the middle of a February blizzard, and entry is free.

The Chicago Theatre's marquee lit up over State Street
The Chicago Theatre's marquee lit up over State StreetPhoto: Maarten van den Heuvel / Unsplash

The 606

An abandoned elevated freight line running nearly three miles above Bucktown, Wicker Park, Logan Square and Humboldt Park, replanted as a walking and cycling trail. It delivers the best rooftop-level view of ordinary Chicago life you can get without a drone.

The market circuit

Green City Market in Lincoln Park is the city's farmers' market of record, with chefs shopping alongside families. The long-running Maxwell Street Market, descended from the city's historic immigrant street bazaar, still trades on Sundays in season, though its location and dates have moved over the years, so confirm before setting off.

Navy Pier's illuminated Ferris wheel stands against the Chicago skyline at dusk.
Navy Pier's illuminated Ferris wheel stands against the Chicago skyline at dusk.Photo: Gautam Krishnan / Unsplash

Pullman

Far on the south side, a nineteenth-century company town built for railway-car workers is now a national historical park. The rows of identical brick houses, the hotel and the old factory administration building make it the strangest and most instructive neighbourhood in the city.

Andersonville

A Swedish neighbourhood that became a quietly cosmopolitan one. Clark Street strings together bakeries, antiques shops, bookstores and a small museum of Swedish-American history, and the whole thing is walkable in an afternoon.

Tip: Pair one neighbourhood with one green space and stop there. Chicago is far bigger than it looks on a map, and three of these in a day means seeing all of them through a train window.

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