Wisconsin State Fair carnival game stock photo

THIS WEEKEND IN CHICAGO – Festing from Morning til Night in Chicago!

Wisconsin State Fair carnival game stock photo

Filling in this week for the great Sue Moss, the weekend after Memorial Day kicks off what many consider the best of the summer season…neighborhood festivals! From now until fall, Chicago’s multicultural communities come alive in celebration. Many are free, and those that have a suggested donation or admission benefit local organizations. 

On Saturday, May 31, from 7am-12pm, start off the day at the Division Street Farmer’s Market, (30 W. Division Street) and browse among their fresh seasonal produce, flowers, prepared foods, unique Chicago-made products and rare finds. Presented by the Department of Cultural Affairs and Special Events, the market runs until Saturday October 25. 

Don your dirndls and lederhosen and step out to Lincoln Square for Maifest Chicago (Lincoln and Leland Avenues), across From The Old Town School of Music. Through Sunday, June 1, witness the crowning of the 2025 Maifest Queen, a traditional keg tapping, decorate the May Pole, sample German and American food, play  carnival games, dance and oom-pa-pa to music, and feel the gemuetlischkeit! 

Chicago’s 4th Annual Windy City Hot Dog Fest, Friday to Sunday, May 30–June 1, in the vibrant Portage Park neighborhood, asks two simple questions: 1) Who has the best hot dog in the city of Chicago? 2) Who will be the hot dog eating champion? Some of Chicagoland’s most iconic hot dog stands will go head-to-head to claim the title of Best Frankfurter—and you get to be the judge! Or … can you down hot dogs like champion Joey Chestnut? Be one of the lucky five people to wolf down as many hot dogs are you can in 5 minutes.  Winner walks away with a trophy and bragging rights! And the fun doesn’t stop at the food. Savor live performances by local and regional artists, explore a variety of arts and crafts vendors, and enjoy family-friendly activities in the kids’ area. 

In West Town, Do Division Street Fest takes place on Division Street (between Damen and Leavitt) from Friday-Sunday. (5-10pm on Friday, noon-10pm on Saturday and Sunday.) A $10 suggested donation  features two live music stages, local designer runway shows and a children’s area with family activities. This kid’s activities include a petting zoo, mega slide and kid-friendly musical performances.

For a completely different experience, Tuley Park’s First Annual Family Chess Fest, 501 E.  90th Place, on Saturday, May 31, (10:30am to 3:30pm) offers outdoor chess games and lessons, food from local vendors, live music, raffles and prizes at this exciting event, sponsored by the Chicago Chess Foundation. Families are encouraged to attend together!

Alison Moran-Powers and Dean’s Team Chicago