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Your Guide to Chicago in May 2024

Posted on May 1, 2024   |   Updated on September 30, 2025
Sidney Madden

Sidney Madden

Customers at Mario's Italian Lemonade stand in 2014

Customers at Mario's Italian Lemonade stand in 2014. (Jeffrey Greenberg / Universal Images Group / Getty)

City Cast

Your Guide to May in Chicago

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Is May the start of Summertime Chi? The weather can be a crapshoot and students are still in school. But festivals are starting to return. Whether you’re ready to jump in or ease into the next season, here’s how to make the most of May in the city.

Have a Taste of Summer

Savor that icy sweetness from Mario’s Italian Lemonade, the 70-year-old Little Italy stand that opens today. Which flavor is calling your name? Blue raspberry? Cantaloupe? Chocolate? You have until September to try them all and other frozen treats.

Celebrate Cultures Respectfully

If you’re going out for Cinco de Mayo this weekend, support Mexican-owned spots like Chile Toreado in McKinley Park. Plus, Pilsen Yards’ 5 Days of Cinco is back. May is also Asian American Pacific Islander Heritage Month: Support AAPI business owners and artists during AAPI Restaurant Week across Chicagoland and the Asian American Showcase at the Gene Siskel Film Center in the Loop.

Treat Your Mom to a Show

Not sure what to do with your mom or mom-like figure for Mother’s Day next weekend? Take her to a show! “Mamma Mia” is at the Nederlander Theatre downtown. Plus, “Mothering the Movement” at Free Street Theater in Pulaski Park tells the story of Hazel Johnson, Chicago’s “Mother of Environmental Justice.”

Free Outdoor Workouts Are Back

Break a sweat early on weekday mornings at Gallagher Way in Wrigleyville with HIIT and yoga classes starting May 13. Or start your Saturday mornings with tai chi, pilates, and other fitness classes at Millennium Park’s Great Lawn starting May 18.

Sueños Festival goers at Grant Park in 2023.

Sueños Festival at Grant Park in 2023. (Natasha Moustache / Getty)

Get Ready for Festival Season

Memorial Day weekend marks Chicago’s unofficial start to street and music festivals including Sueños in Grant Park and Mole de Mayo in Pilsen. Our tips? Pack light, dress comfortably, and stay hydrated.

City Cast

How to Do Chi Music Fests Right

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Hang With City Cast Chicago’s Jacoby Cochran!

Karaoke Storytellers at Steppenwolf Theatre in Lincoln Park this weekend might be sold out, but you can try your luck for standby tickets to the singing-storytelling show. Our podcast host will also discuss the history of Black Chicago with author Arionne Nettles May 13 at the new Call & Response bookstore in Hyde Park.

City Cast

Finding Love, Home, and Yourself: Stories from Karaoke Storytellers

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🧠 Plus, Mental Health Awareness Month tips

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