Looking for Chicago street festivals this weekend? May 2026 has three to put on your calendar, spread across Lincoln Park, Lakeview, and Portage Park. Here is the list, with dates, hours, and the link to grab tickets or vendor info on Eventeny.
Lincoln Park Mayfest
Starts on Friday, May 15th, 2026
Mayfest is the first big Chicago street festival of the season. It runs in the heart of Lincoln Park, surrounded by the neighborhood's boutiques, restaurants, and historic blocks. The lineup features local bands, artisan vendors, food booths, and a full drink menu. Good for a long afternoon or all three days.
Event page: https://www.eventeny.com/events/lincoln-park-mayfest-2026-24412/
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Belmont-Sheffield Music Fest
Starts on Friday, May 22nd, 2026
Now in its 41st year, Belmont-Sheffield takes over Lakeview steps from the Belmont El stop. The main stage near Roscoe leans into Chicago tribute bands. The community stage near Belmont highlights neighborhood DJs and local performers. Expect food, beer, wine, and a full block of artisans and small business vendors. One of the longest-running music fests in the city.
Event page: https://www.eventeny.com/events/belmont-sheffield-music-fest-2026-24342/
Want to sell at Chicago Street Festivals? Browse open vendor applications.
Windy City Hot Dog Fest
Starts on Friday, May 29th, 2026
The 5th annual Windy City Hot Dog Fest lands in Portage Park and settles the ketchup debate once and for all. Chicagoland's hot dog stands compete head to head for Best Frankfurter, and attendees do the judging. There is a main music stage, a community stage for local talent, an arts and crafts market, and a family activity zone for the kids. Presented in partnership with the Six Corners Chamber of Commerce.
Event page: https://www.eventeny.com/events/windy-city-hotdog-fest-2026-24812/
Save the Guide
That's the full Eventeny schedule of Chicago street festivals this weekend and across May 2026. Bookmark this guide, share it with friends, and check Eventeny for updates, vendor applications, and ticket links as each event gets closer.