Monday, June 23, 2025

Things to Do in Chicago This Weekend

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Introduction to Chicago’s Weekend Events

Chicago is a vibrant city with a wide range of activities to enjoy every weekend. From festivals and fairs to concerts and dance performances, there’s something for everyone in this bustling metropolis.

Festivals and Fairs

Lincoln Roscoe Art & Craft Fair

The Lincoln Roscoe Art & Craft Fair, hosted by Lakeview SSA 27, features juried art, including paintings, sculptures, jewelry, and more, all handmade by artists and artisans.

  • WHERE: On Lincoln Avenue between Roscoe and Melrose
  • WHEN: Saturday, May 17, 10 a.m.-6 p.m., Sunday, May 18, 10 a.m.- 5 p.m.

Lincoln Park Mayfest

The 4th annual Lincoln Park Mayfest features top local bands, artisans, and a kids’ area. New this year, a Spring Fine Art Mart featuring local and national fine artists.

  • WHERE: 1000 W. Armitage Ave., Chicago
  • WHEN: Friday, May 16 – Sunday, May 18

Pullman Railroad Days

Pullman Railroad Days, billed as Chicago’s biggest rail-themed event, features gorgeously restored railcars thanks to a partnership with Metra and the American Association of Private Railroad Car Owners (AAPRCO).

  • WHERE: The 111th Street Pullman/Metra Electric Station
  • WHEN: Saturday, May 17, and Sunday, May 18

Events and Exhibitions

Wright Plus Architectural Housewalk

The Wright Plus Architectural Housewalk features tours inside eight private residences designed by Frank Lloyd Wright and his contemporaries.

  • WHERE: Oak Park, IL
  • WHEN: Saturday, May 17

Maxwell Street Market

Maxwell Street Market opens this weekend for the season, featuring an eclectic mix of foods and finds, including handmade crafts, resale housewares, clothing, and much more.

  • WHERE: Maxwell Street between South Halsted Street and South Union Avenue
  • WHEN: Sunday, May 18, 10 a.m.-3 p.m.

Film Screenings and Concerts

Film Screening/Concert: Harry Potter and the Chamber of Secrets

Conductor Ron Spigelman leads Orchestra 220 in John Williams’ score to Harry Potter and the Chamber of Secrets alongside a high-definition screening of the film.

  • WHERE: Symphony Center, 220 S. Michigan Ave., Chicago
  • WHEN: Friday, May 16 – Sunday, May 18

Dance Concerts

Hubbard Street Dance Chicago

Hubbard Street Dance Chicago’s Season 47 Spring Series features "Sweet Gwen Suite" by Bob Fosse and Gwen Verdon.

  • WHERE: Harris Theater for Music and Dance, 205 E. Randolph St., Chicago
  • WHEN: Friday, May 16 – Sunday, May 18

Trinity Irish Dancers

Chicago-based Trinity Irish Dance Company launches its 35th anniversary season with four shows this weekend.

  • WHERE: Museum of Contemporary Art, 220 E. Chicago Ave., Chicago
  • WHEN: Friday, May 16 – Sunday, May 18

Hiplet Ballerinas of Chicago

Hiplet Ballerinas of Chicago fuse classical pointe technique with African, Latin, Hip-Hop, and urban dance styles rooted in communities of color.

  • WHERE: The Auditorium, 50 E. Ida B. Wells Dr., Chicago
  • WHEN: Saturday, May 17, 7:30 p.m.

Music Concerts

Anthony Hamilton & Vivian Green

Grammy Award-winning R & B singer Anthony Hamilton, along with singer-songwriter and pianist Vivian Green, perform in Chicago.

  • WHERE: The Chicago Theatre, 175 N. State St., Chicago
  • WHEN: Saturday, May 17, 8 p.m.

Beyoncé

One of the most awarded artists in Grammy history, Beyoncé brings her Cowboy Carter Tour to Chicago.

  • WHERE: Soldier Field, 1410 Special Olympics Dr., Chicago
  • WHEN: Thursday, May 15, Saturday, May 17, and Sunday, May 18

Conclusion

Chicago offers a diverse range of activities this weekend, from art fairs and railroad days to dance performances and concerts. Whether you’re interested in history, art, music, or dance, there’s something for everyone to enjoy in this vibrant city.

FAQs

  • Q: What are the main events happening in Chicago this weekend?
    A: The main events include the Lincoln Roscoe Art & Craft Fair, Lincoln Park Mayfest, Pullman Railroad Days, and several concerts and dance performances.
  • Q: Where can I find more information about the events?
    A: More information about each event, including locations and times, can be found in the respective sections above.
  • Q: Are there any events suitable for children?
    A: Yes, events like the Lincoln Park Mayfest and the Maxwell Street Market are family-friendly and offer activities for children.
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