Hey Chicago!
Spring finally feels like it’s here, and April and May are looking like two of the busiest months of the year. Whether you’re into art fairs, film festivals, outdoor markets, or just getting back outside after a long winter, there’s a lot going on across the city and the suburbs over the next couple of months.
In this week’s article, we’ll cover all the events that are happening around Chicago over the next 2 months.
If you’re new here, hi! We’re the Ben Lalez Team, an award-winning real estate team in Chicago and Illinois. We’ve been helping families buy and sell homes across Chicago for over a decade, and every week we publish an article about something interesting or useful in Chicago.
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Let’s get into this week’s article.
Events At A Quick Glance
| Date | Event | Location |
| Apr 9 – 12 | EXPO CHICAGO Contemporary Art Fair | Navy Pier |
| Apr 9 – 12 | The Other Art Fair | Artifact Events |
| Apr 16 – 27 | 42nd Chicago Latino Film Festival | Landmark Century Centre, Lakeview |
| Apr 18 | Chicago Humanities Festival: Bridgeport Day | Bridgeport |
| Apr 24 – 26 | One of a Kind Spring Show | The Mart |
| Apr 24 – 26 | CineYouth Festival | FACETS, Lincoln Park |
| Mar 19 – May 10 | Glow Wild: A Lantern Festival of Hope | Brookfield Zoo |
| May 16 | Division Street Farmers Market Opens | Division Street |
| May 21 | Daley Plaza Farmers Market Opens | The Loop |
| May 23 | Memorial Day Parade & Wreath Laying | Downtown |
| May 23 – 24 | Sueños Music Festival | Grant Park |
April 2026
EXPO CHICAGO Contemporary Art Fair
Apr 9 – 12
EXPO CHICAGO is back at Navy Pier’s Festival Hall for its annual contemporary art fair, bringing galleries from around the world together with curated talks, on-site installations, and special programming.
If you follow the Chicago art scene at all, this is the big event of the spring you need to be at.
Running alongside it is EXPO Art Week, a citywide slate of exhibitions and events that happen in galleries and institutions across the city. So even if you don’t go to the fair itself, you’ll likely notice something happening in your neighborhood that week.
The Other Art Fair
Apr 9 – 12
Running at the same time as EXPO, The Other Art Fair offers a more direct-to-artist experience with up-and-coming creators. If you want to skip the big-gallery atmosphere and buy directly from the people making the work, this is a good option for you. The two fairs together make April 9–12 one of the best weekends of the year for anyone interested in contemporary art, so get ready this week!
42nd Chicago Latino Film Festival
Apr 16 – 27
The Chicago Latino Film Festival is in its 42nd year, running at Landmark Century Centre Cinemas in Lakeview. Nearly 100 short and feature films from Latin America, Spain, Portugal, and the United States are on the schedule.
Chicago Humanities Festival: Bridgeport Day
Apr 18
The Chicago Humanities Festival runs a spring series of neighborhood-focused days, and Bridgeport Day is on Saturday, April 18. It’s a day of talks, tours, and programming in the Bridgeport neighborhood, with authors, journalists, and public thinkers involved.
Additional spring days in Lakeview and at Northwestern University follow in May (the 9th and 17th). Make sure to check their website for details about these upcoming events.
One Of A Kind Spring Show
Apr 24 – 26
The One of a Kind Spring Show is at The Mart for three days, with artists and makers selling handmade goods, jewelry, homewares, and gifts. Good for a Saturday afternoon if you’re looking for something a little different. Tickets are on sale at their website.
CineYouth Festival
Apr 24 – 26
CineYouth is organized by Cinema/Chicago and takes place at FACETS in Lincoln Park. All the films are made by directors no older than 22 years old from Chicago and around the world, and public screenings are free.
It’s a genuinely interesting event, and if any of your kids are into filmmaking, this could really inspire them.
Ongoing Through MayGlow Wild: A Lantern Festival Of Hope At Brookfield Zoo
Through May 10
Glow Wild is still running until May 10, and if you haven’t been, you’ll want to pop by.
It transforms Brookfield Zoo after dark with more than 70 illuminated lantern displays of wildlife and mythological figures, cultural performances, and global music and food. Ticket price includes rides on the Carousel and Ferris wheel, as well as event parking. Adults are $19.95, and children are $9.95.
It’s an after-hours ticketed event, so this is not your typical daytime zoo trip. We’d recommend buying tickets in advance, since it’s been busy on weekends.
May 2026
Division Street And Daley Plaza Farmers Markets Open
May 16 And May 21
The city’s farmers market season gets going in mid-May. The Division Street Farmers Market opens on May 16th, and the Daley Plaza Farmers Market follows on May 21st. Both markets run through October and are free to walk through.
Millennium Park Summer Workouts
Starting May 16
Also kicking off on May 16th, the city’s Millennium Park Summer Workouts happen on Saturdays on the Great Lawn through early September. It’s free, and if you’ve never done a workout with the skyline behind you, it’s a pretty good way to spend a Saturday morning.
Maxwell Street Market Opens For The Season
May, Sundays
The Maxwell Street Market on South Halsted Street reopens for Sundays starting in May and runs through October. Street food, vintage goods, and vendors of all kinds. It’s been part of Chicago’s open-air market culture for a long time.
Memorial Day Parade And Wreath Laying Ceremony
May 23
The city’s Memorial Day Wreath Laying Ceremony and Parade is downtown on Saturday, May 23. It’s a formal civic event and a good way to mark the unofficial start of summer in the city.
Sueños Music Festival
May 23 – 24
Sueños is a Latin music festival in Grant Park that returns for its fifth year on May 23rd and 24th. The lineup includes Fuerza Regida, J Balvin, Kali Uchis, and Ryan Castro across three stages, with local food vendors, art installations, and brand activations throughout the weekend.
A Few Other Things Worth Knowing About
If you’re interested in architecture, the river cruise has just started. The Chicago Architecture Center river cruise is 90 minutes and covers all three branches of the river with a certified docent guiding the whole thing. It’s a great way to see the skyline and understand the city’s architecture.
The Titanic: A Voyage Through Time immersive VR experience at 108 West Germania Place is running through May 31st if you’re looking for something a little out of the ordinary. It lets you explore the Titanic both as a present-day wreck and as it looked in 1912.
And for baseball fans, the Cubs are home at Wrigley throughout April and May with matchups against teams like the Arizona Diamondbacks on May 1. The White Sox also have home dates in April.
Final Thoughts
April and May are the two months when it feels like Chicago starts coming back to life after the long winter, and this year there’s a lot to take advantage of before the bigger summer festivals get going in June and July (we’ll write about those in the coming weeks, so make sure to check back here).
If you’ve been thinking about making a move and want to get a feel for different neighborhoods, there’s no better time than spring to explore!
Come out to a film festival in Lakeview, check out the markets in the Loop, or drive out to Brookfield for a Saturday night at Glow Wild. You’ll get a real sense of what it feels like to live in these areas.
And if you want to talk real estate while you’re at it, give us a shout. We’d be happy to help.
Until next week, enjoy the warmer weather and the festivities!
