Monday, June 23, 2025

Things to Do in Chicago Area

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Things to do in Chicago area

The Chicago area is bustling with exciting events and activities to enjoy this weekend. From music festivals to comedy shows, there’s something for everyone to enjoy.

Upcoming Events

Music Festivals

Some of the notable music festivals happening this weekend include:

  • Sueños Music festival: Shakira, Peso Pluma and Don Omar are among the many Latin artists and Reggaeton performers participating in the Sueños Music Festival.
    • WHERE: Grant Park near Roosevelt Road and Columbus Drive
    • WHEN: Saturday, May 24 – Sunday, May 25
  • Belmont-Sheffield Music Fest: 40th annual Belmont-Sheffield Music Fest kicks off Friday evening in the heart of Lakeview, featuring tribute bands, artisans, vendors and community entertainment.
    • WHERE: 3200 N. Sheffield Ave.
    • WHEN: Friday, May 23 – Sunday, May 25
  • Rosemont’s Rockin’ in the Park Free Concert Series: Adult alternative rock group Pino Farina Band kicks off the free Rockin’ in the Park concert series, followed by a fireworks display.
    • WHERE: Parkway Bank Park Entertainment District, 5501 Park Place, Rosemont, IL
    • WHEN: 7 p.m. Sunday, May 25

Food and Drink Festivals

  • Mayfestiversary: Join Begyle Brewing and Dovetail Brewery as they host their 9th annual spring celebration, Mayfestiversary, and commemorate the 10th anniversary of Dovetail Brewery.
    • WHERE: 1800 W. Cuyler Ave., Chicago
    • WHEN: Saturday, May 24, and Sunday, May 25

Markets and Fairs

  • Randolph Street Market Festival: Randolph Street Market Festival is an antique and vintage flea market featuring thousands of goods from dealers around the country.
    • WHERE: 1341 W. Randolph St., Chicago
    • WHEN: 10 a.m.-5 p.m. Saturday, May 24, and Sunday, May 25
  • Turkish Festival: Turkish Festival, a cultural heritage convention, brings together a rich blend of traditions, art, music, food and films around the Islamic traditions of Türkiye and the Ottoman Empire.
    • WHERE: Stephens Convention Center, 5555 N. River Road, Rosemont, IL
    • WHEN: Friday, May 23 -Sunday, May 25

Theater and Comedy

Theater

  • ‘Shakin’ the Mess Outta Misery’: Pegasus Theatre Chicago’s revival of "Shakin’ the Mess Outta Misery" reimagines and celebrates Shay Youngblood’s story of a young Black girl’s coming of age during the turbulent 1960s.
    • WHERE: Chicago Dramatists, 1105 W. Chicago Ave., Chicago
    • WHEN: Runs through Sunday, June 15

      Comedy

  • Tony Rock: American comedian, actor and younger brother of famed comedian Chris Rock, Tony Rock, performs three shows in north suburban Schaumburg.
    • WHERE: Chicago Improv, 5 Woodfield Mall Store K120B, Schaumburg, IL
    • WHEN: Friday, May 23, and Saturday, May 24

Concerts and Performances

  • Chicago Human Rhythm Project: The Chicago Human Rhythm Project (CHRP) reimagines its Stomping Ground Festival with a double header: two free performances featuring Irish, African, Mexican, Tap and more.
    • WHERE: National Museum of Mexican Art, 1852 W. 19th St., Chicago
    • WHEN: 3 p.m. and 6 p.m. Sunday, May 25
  • Paul Simon: Famed singer-songwriter Paul Simon performs his critically acclaimed, Grammy-nominated album Seven Psalms, as well as timeless classics.
    • WHERE: Symphony Center, 220 S. Michigan Ave., Chicago
    • WHEN: 8 p.m. Friday, May 23, and Saturday, May 24
  • Vince Gill: Country crooner Vince Gill performs in Chicago this weekend.
    • WHERE: The Chicago Theatre, 175 N. State St., Chicago
    • WHEN: 7:30 p.m. Friday, May 23
  • Chanté Moore: Known for capturing the highs and lows of love through her songs, Chanté Moore is ready to share her inspiring story with the world through new music and live stage performances.
    • WHERE: Rialto Square Theatre, 102 N. Chicago St., Joliet, IL
    • WHEN: 8 p.m. Friday, May 23
  • AC/DC: Australian rock band AC/DC is considered a formative influence on the new wave of British heavy metal bands.
    • WHERE: Soldier Field, 1410 Special Olympics Dr, Chicago
    • WHEN: 8 p.m. Saturday, May 24

Conclusion

The Chicago area has a wide range of events and activities to enjoy this weekend, from music festivals to comedy shows and concerts. Whether you’re interested in trying new foods, listening to live music, or exploring new cultures, there’s something for everyone to enjoy.

FAQs

  • Q: What is the Sueños Music festival?
    • A: The Sueños Music festival is a music festival featuring Latin artists and Reggaeton performers, including Shakira, Peso Pluma, and Don Omar.
  • Q: Where can I find more information about the Belmont-Sheffield Music Fest?
    • A: You can find more information about the Belmont-Sheffield Music Fest on the official website or by visiting the event’s social media pages.
  • Q: Are there any free events happening in the Chicago area this weekend?
    • A: Yes, there are several free events happening in the Chicago area this weekend, including the Rockin’ in the Park Free Concert Series and the Chicago Human Rhythm Project’s Stomping Ground Festival.
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