City Cast Chicago logo
Display Ad: Enjoy Illinois, Meet in the middle

Your Guide to May 2026

Posted on May 4
Emily Mack

Emily Mack

Two people posing for a photo at their booth. There is a sign that says "eggs for sale" and an assortment of flowers, and fruit at the stand

The Wicker Park Farmers Market. (Courtesy of Makena Torrey)

May kicked off with a jolt on Friday as Chicagoans turned out to celebrate May Day all across the city. I expect the energy will stay high all month long — a lot is going on!

Farmers Markets in Full Force

Although some operate during colder months, true Chicago farmers market season begins in May. Twelve seasonal markets start back up this month, stretching across the city from 95th Street to Uptown. Find your nearest farmers market!

Asian American and Pacific Islander Heritage Month

May is AAPI Month. Here’s how Chicago is celebrating:

📆 Stay tuned all month long for more AAPI events!

Arts Events

The Chicago Critics Film Festival continues through Thursday — catch “The Sun Never Sets” and director Joe Swanberg at the Music Box on closing night.

Chicago Humanities Festival is hosting Lakeview Day on May 9 and Northwestern Day on May 17. Speakers include Padma Lakshmi, Peter Sagal, Mary Beard, John Waters (!!!), and Rep. Lauren Underwood (14th).

Art on the Mart projections have already returned to the side of Merchandise Mart. This month, the projection features works by current School of the Art Institute and Chicago Public Schools students. Catch it Thursday through Sunday evenings.

Sky Shakeup, Sox Hot Streak

After a massive trade, all eyes are on the Chicago Sky. The Sky’s season starts May 9. Meanwhile, White Sox first baseman Munetaka Murakami is riling fans up with his home-run hot streak. The team recently had its highest April attendance for a non-opener in 19 years. Get May tickets while you can!

More Almost-Summer Fun

Beginning Memorial Day weekend, twice-weekly fireworks return to Navy Pier. Catch them Wednesdays at 9 p.m. and Saturdays at 10 p.m. Chicago’s beaches open May 22.

The final weekend of May, the German Maifest returns to its original home in Lincoln Square. Grab a pint and get ready for warmer months ahead. Prost!

Share article

Hey Chicago

Stay connected to City Cast Chicago and get ready to join the local conversation.

Can't subscribe? Turn off your ad blocker and try again.