★ Editor’s pick

First Time in Chicago? The Perfect Weekend Itinerary

New to Chicago? Hit the icons, the culture, and the local flavour in one well-paced weekend.

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SaturdaySat, May 30

Morning

arts10:00 AM

Magnificent Mile Spring Art Festival

Browse 60+ juried artists showcasing jewelry, paintings, and glass on the Magnificent Mile.

875 N Michigan Ave · Streeterville📅 Add to calendar

food11:00 AM

Windy City Hot Dog Fest

Grab an iconic Chicago hot dog and enjoy live music at Portage Park.

Portage Park, 4000 N Milwaukee Ave · Portage Park📅 Add to calendar

Afternoon

arts1:00 PM

Chicago Dance Month Kickoff

Catch free dance performances launching Chicago Dance Month at Navy Pier.

Navy Pier Lake Stage · Streeterville📅 Add to calendar

landmark

Cloud Gate (The Bean)

Snap a selfie at the iconic mirrored Bean in Millennium Park.

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Evening

attraction

Navy Pier

Stroll Navy Pier, ride the Ferris wheel, and watch for fireworks over Lake Michigan.

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SundaySun, May 31

Morning

food8:00 AM

Wicker Park Farmers Market

Shop for fresh produce and local crafts at the Wicker Park Farmers Market.

Wicker Park, 1425 N Damen Ave · Wicker Park📅 Add to calendar

Afternoon

food11:00 AM

Street Foods of Pilsen Food Tour

Taste your way through Pilsen's celebrated Mexican food scene on a guided tour.

5 Rabanitos, 1758 W 18th St · Pilsen📅 Add to calendar

Evening

museum

Art Institute of Chicago

Explore world-class art, from Impressionist masterpieces to American Gothic.

111 S Michigan Ave📅 Add to calendar

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Built from Weekend Hive’s verified local listings — every stop links to its full details.