Experience Chicago Like a Local: Eat, Shop, Drink

Chicagoans play in the city’s parks, tour art exhibits, cheer the Cubs, and eat, eat, eat. Chicago is a foodie city, from the groundbreaking culinary inventions at Alinea to classic, only-in-Chicago staples like beef sandwiches, hot dogs, and, of course, the best pizza anywhere. If there’s a Cubs game on, you’ll find locals filing into Wrigley Field or watching the game at a Lakeview bar. Here are some of the best ways to experience Chicago like a local.

Logan Square, in the Bucktown and Wicker Park neighborhoods, and the West Side are popular areas for locals to eat and drink. Wicker Park and Lincoln Park offer great neighborhood boutiques. In summer, Chicagoans flock to the beach, get out on the water, and stroll the Riverwalk at night.

pathway along water with a view of the Chicago skyline
Lincoln Park. Photo © Exflow/Dreamstime.

To see Chicago like a local, ride the L train to the city’s neighborhoods to explore . . . and avoid the Loop (as do most Chicagoans).

Morning in Bucktown and Wicker Park

Start your morning in the Bucktown and Wicker Park neighborhoods with an espresso from Buzz Killer and a coconut cake doughnut from Stan’s Donuts, a must-try when in Chicago. Wicker Park is packed with local boutiques, art galleries, and specialty food stores. Wander the shops along Damen and Milwaukee Avenues; stop in Virtu to admire the unique collection of jewelry and gifts. Once your caffeine wears off, claim a spot on the patio at Big Star and order some of their inventive tacos.

tacos on a plate at Big Star in Chicago
The tacos at Big Star are among the best in the city. Photo © Rebecca Holland.

Afternoon in Lakeview

In the afternoon, head to the Lakeview neighborhood. You’ll know whether the Cubs are playing at Wrigley Field; just look for sports bars like The Cubby Bear and Sluggers filled with locals. Pop inside for a bit of the excitement or a beer, then walk south along North Broadway. Take time to stop at shops like Windy City Sweets, Foursided, and the Unabridged Bookstore. Relax with a bite to eat at Bar Pastoral.

a Chicago street near Wrigley Field is filled with people at sunset
Crowds flock to Wrigley Field on game day. Photo © Rebecca Holland.

Evening in the West Loop

At night, head to the trendy West Loop for dinner. Make reservations at local favorite Girl & the Goat and tuck in to family-style plates off the global menu. After dinner, indulge in inventive cocktails at The Aviary. Or, if you’re ready for a new ‘hood, take the Blue Line north to Logan Square, west Bucktown. Specialty cocktail spots like Lost Lake, Billy Sunday, and Scofflaw all sit within a few blocks of each other.

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