May 16, 2024 - Things to Do

Chicago weekend events: Mayfest, Margarita Fest, Megan Thee Stallion

Crowd watching concert at 2023 Mayfest

2023 Mayfest. Photo: Valerie Loeblich

This weekend in Chicago, attend the first major festival of the summer, sip on 15 different margaritas or rap along with Megan Thee Stallion.

1. 🎸 Mayfest

Known as the first major festival of the summer, Lincoln Park's Mayfest offers live music, local food and art.

Why it matters: The event's proceeds will benefit Ranch Triangle, a nonprofit that supports small businesses, schools and parks in the neighborhood.

What to expect: There will be performances by bands on two stages, a pet parade, an art show and glass blowing classes.

  • Headliners include Too Hype Crew, Mr. Simpson and Monty Kiddo.

When: 5–10pm Friday, noon–10pm Saturday, noon–9pm Sunday

Address: 1000 W. Armitage Ave.


2.🍸 Chicago Margarita Fest

  • Head to Pilsen for this three-day festival featuring over 15 kinds of margaritas, live music, Latin food and merchandise from local vendors. Donations accepted
  • When: 5–10pm Friday, noon–10pm Saturday and Sunday

3. 🐴 Megan Thee Stallion

  • The Hot Girl Summer Tour arrives in the Windy City for two performances at the United Center. Tickets start at $70
  • When: 8pm Friday and Sunday

4.🍿 Asian American Film Showcase

  • See documentaries, shorts and dramas from Asian American filmmakers including the critically acclaimed "Dìdi," which premiered at Sundance. Non-member tickets start at $13
  • When: Friday through May 26

5. 😂 D.L. Hughley

  • The comedian and radio host will take the stage at Improv at Woodfield Mall for six shows. Tickets are $44
  • When: 7pm and 9:30pm Friday–Sunday

6. 🎵 Aventura


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