Juliana Yeager

May is coming to a close! Check out some of the amazing events happening this weekend for families and adults below!

girl arranging displays for sale
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Do Division Street Fest

Kick off the summer festival season at Do Division, a lively street event in West Town featuring live music curated by Empty Bottle and Subterranean. Enjoy performances on two stages, with acts like Divino Niño, Arm’s Length, Susto, and Avey Tare. Explore food trucks, a fashion show, various vendors for shopping, and a Family Fun Fest area with activities for kids, among other attractions.

train rail during golden hour
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Railroad Days

Calling all train enthusiasts! Immerse yourself in locomotive history at the Historic Pullman Foundation’s two-day Pullman Railroad Days event. This exciting weekend brings three historic Pullman Cars to the 111th Street/Pullman Metra Electric station, along with a host of other train-related activities. Visitors can explore the 1950 Pullman Sleeper-Observation Blue Ridge Club, the 1934 Sleeper-Lounge Dover Harbor, and the 1957 Art Deco beauty, Hollywood Beach. Plus, enjoy guided tours, live music, a vendor fair, and family-friendly activities.

two yellow labrador retriever puppies
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Bark at the Ballpark

Bring your furry best friend to Impact Field, home of the independent professional baseball team, The Chicago Dogs, for an evening of dog-friendly fun! The first 1,500 fans will receive a bandana for their pups upon entry, and all pets are welcome to run the bases after the game. Tickets start at just $9.

woman standing near paintings holding white hammock
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Street Art Fair

The oldest juried craft fair in Hyde Park showcases paintings, sculptures, jewelry, and ceramics from nearly 200 artists. The event also features blues and jazz performances, presented by Buddy Guy’s Legends, along with a family-friendly activity area and various food vendors. Attendees can shop for artwork in a variety of mediums, including glass, jewelry, leather, photography, printmaking, painting, sculpture, wood, ceramics, and fiber.


Enjoy Chicago!