May 30, 2024 - Things to Do

Chicago weekend events: 57th Street Art Fair, Anitta, Gospel Music Fest

Guests browsing paintings at the 57th Street Art Fair.

Guests browsing paintings at the 57th Street Art Fair. Photo: Courtesy of 57th Street Art Fair

This weekend in Chicago, browse art in Hyde Park, see pop superstar Anitta in concert or lift your hands to gospel in Millennium Park.

1. 🎨 57th Street Art Fair

One of the longest-running juried art festivals in the Midwest is almost here.

Why it matters: Nearly 200 artists are presenting work and between 15,000–20,000 people are expected to attend the 57th Street Art Fair in Hyde Park.

  • Over 60 artists are new this year and 30 are from Illinois.

The artwork includes wood, paintings, textiles, ceramics, glass and studio jewelry.

What to expect: A new food truck social area. Grab a bite from Da Local Boy, Happy Lobster, El Buen Taco, Royal Ice Cream, Robinson's and Reggie's.

  • The kids can enjoy a playground and a designated area that includes a Lego table and a salad spinner wearable art project (make your own pin).

When: 11am–6pm Saturday, 10am–5pm Sunday.


2. 🎵 Chicago House Music Festival

3. 🏳️‍🌈 Pride Month Kickoff Party

  • Celebrate Pride Month with Chicago Fire FC and the Lesbian Social Club 10pm Saturday at TAO Chicago. Tickets start at $10
  • If you go: Guests who have a ticket to the Fire's match against the LA Galaxy, will get free entry.

4. 🪩 Anitta

  • The fine print: This event is for ages 17+.

5. ⚽ Mexico vs. Bolivia

  • Catch these two national soccer teams 8pm Friday at Soldier Field before they compete for the Copa América trophy. Tickets start at $65
  • If you go: Check out a pre-match festival 3:30–7:30pm in the Stadium Green.

6. 🚂 Pullman Railroad Days

  • Tour historic rail cars and model trains while enjoying live music and food from local restaurants at Pullman National Historical Park 9am–5pm Saturday and Sunday. Tickets
  • Cost: Children under 12 free, adults $26.

7. 🎵 Gospel Music Fest

  • The Clark Sisters, Chandler Moore, Anita Wilson and Todd Dulaney headline this celebration of inspirational music in Millennium Park 4–9pm Saturday. Free

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