Things to Do in Chicago and DuPage – Weekend Guide (May 1 – May 3, 2026)

If you're looking for plans this weekend, Chicago is packed with festivals, live performances, and cultural experiences, while DuPage County offers a mix of outdoor events, local markets, and unique exhibits. Here’s a curated guide to help you make the most of May 1–3.

CHICAGO WEEKEND HIGHLIGHTS

Friday, May 1, 2026 (Chicago)

Mexico Fest at Navy Pier – Celebrate Mexican culture with live music, dance, workshops, and a vibrant vendor market.
Chicago Cubs vs. Arizona Diamondbacks – Catch the Cubs in action at Wrigley Field for a classic Chicago sports experience.
Trading Card Con – A must-visit for collectors and hobbyists featuring trading cards, memorabilia, and vendors.
Wicker Park Bucktown First Fridays Art Walk – Explore local galleries and discover emerging artists in one of Chicago’s most creative neighborhoods.
An Evening With South Chicago Dance Theatre – Enjoy a powerful live performance at the Harris Theater.

Saturday, May 2, 2026 (Chicago)

135th Annual Polish Constitution Day Parade – One of Chicago’s biggest cultural parades celebrating Polish heritage.
Chicago Fireboat Tours Busse Birthday Bash – Step aboard a historic fireboat for a unique waterfront celebration.
The Head and The Heart at Auditorium Theatre – A high-energy live concert from the popular indie folk band.
You Win Some, You Dim Sum (Comedy Show) – A fun, interactive comedy experience paired with delicious dim sum.
Dovetail Brewery Tour – Go behind the scenes of one of Chicago’s most unique breweries and sample craft beers.

Sunday, May 3, 2026 (Chicago)

Doc10 Film Festival – Chicago’s premier documentary film festival featuring compelling stories from around the world.
The Great Gatsby (Broadway in Chicago) – Experience the iconic novel brought to life on stage.
Spring Flower Show: Showers of Flowers – A colorful seasonal display at Garfield Park Conservatory featuring vibrant hanging gardens.
The Merry Wives of Windsor – A lively Shakespeare comedy full of wit and charm.
Glow Wild at Brookfield Zoo – Walk through illuminated lantern displays in this magical nighttime zoo experience.

DUPAGE WEEKEND HIGHLIGHTS

Looking for something a little more laid-back this weekend? DuPage offers a mix of nature, live music, and casual experiences perfect for a slower pace.

Friday, May 1, 2026 (DuPage)

America 250 Elmhurst – A citywide celebration honoring America’s 250th anniversary with community programming.
Cabinet of Curiosities Exhibit – Discover fascinating historical artifacts at the DuPage County Historical Museum.
Cocktail for a Cure – Enjoy cocktails while supporting a meaningful cause in Oak Brook.
Craft by Beer (Naperville Settlement) – A hands-on brewing experience perfect for beer enthusiasts.
Father of the Bride (Theatre) – A heartwarming stage production at Drury Lane Theatre.

Saturday, May 2, 2026 (DuPage)

Art in Wilder Park – A popular outdoor art festival featuring local artists and vendors in Elmhurst.
Go Fly a Kite at Graf Park – A fun, family-friendly event perfect for enjoying spring weather.
Lilac Time Festival (Lombard) – Celebrate blooming lilacs with seasonal festivities and community events.
Rare Earths & Beyond Exhibit – Explore the science behind minerals used in modern technology.
Spring Tea at Hotel Arista – A relaxing and elegant afternoon tea experience in Naperville.

Sunday, May 3, 2026 (DuPage)

Weekend Brunch Buffet (Pinstripes Oak Brook) – Enjoy a classic brunch with family and friends.
Wheaton French Market – Shop fresh produce, artisan goods, and local specialties in a charming outdoor market.
Beauty and Brunch Event – A unique mix of beauty experiences and brunch in Woodridge.
Galliversario 19 Festival – A lively cultural celebration featuring music and entertainment.
Tailwagger Trot 5K (Lisle) – A fun run supporting local animal causes, perfect for pet lovers.

Weekend Wrap-Up

From major festivals and live performances in Chicago to relaxed outdoor events and community experiences in DuPage County, this weekend offers something for everyone. Plan ahead, mix city energy with suburban charm, and make the most of your May 1–3 plans.

Explore more Chicago events, from winter festivals to culinary celebrations and performing arts.

See DuPage’s full event calendar for all events happening this weekend and beyond.

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