Things to Do in Chicago and DuPage – Weekend Guide (March 27 – March 29, 2026)
Chicago is packed this weekend with major events, from one of the biggest pop culture conventions in the Midwest to March Madness basketball and live performances across the city. Whether you’re heading downtown or staying in the suburbs, here’s your curated guide to what’s happening.
CHICAGO WEEKEND HIGHLIGHTS
March 27, 2026 – Friday Highlights (Chicago)
C2E2: Chicago Comic & Entertainment Expo – McCormick Place
One of the biggest events of the weekend kicks off Friday. Expect celebrity guests, cosplay, panels, gaming, and hundreds of vendors at this massive pop culture convention.NCAA March Madness Midwest Regional – United Center
Experience the energy of college basketball as March Madness takes over Chicago for a multi-day tournament featuring top teams.Hamilton – CIBC Theatre
Catch the award-winning Broadway hit as it continues its Chicago run with powerful storytelling and unforgettable music.Spring Festival of New Plays and Musicals – Various Venues
Discover new voices in theatre with staged readings of original works from emerging playwrights.Live Music & Shows Across Chicago – Multiple Venues
From concerts at Aragon Ballroom to Orchestra Hall performances, Friday night is packed with live entertainment options.
March 28, 2026 – Saturday Highlights (Chicago)
Indiana Jones and the Raiders of the Lost Ark in Concert – Auditorium Theatre
Watch the iconic film with a live orchestra performing the legendary score, creating a unique cinematic experience.Chicago River & Dinner Cruises – Chicago Riverwalk Area
Take in skyline views with a scenic dinner cruise or architecture tour along the Chicago River.March Madness Weekend Atmosphere – Downtown Chicago
Even outside the arena, the city is buzzing with watch parties, sports bars, and fan energy throughout the weekend.
March 29, 2026 – Sunday Highlights (Chicago)
Final Day of C2E2 – McCormick Place
Wrap up the weekend with more panels, shopping, and fan meetups at one of Chicago’s biggest annual events.March Madness Games Continue – United Center
Catch the final matchups of the Midwest Regional as teams battle for a spot in the next round.Museum & Cultural Experiences – Citywide
Spend a relaxing Sunday exploring Chicago’s top museums and exhibitions across the city.Live Theatre & Performances – Multiple Chicago Venues
End the weekend with a show, from Broadway productions to local theatre performances.
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.
March 27, 2026 – Friday Highlights (DuPage)
Friday Night Live Music – Church Street Brewing Company, Itasca
Kick off the weekend with live music, craft beer, and a relaxed neighborhood vibe at one of DuPage’s go-to breweries.All You Can Eat Fish Fry – Prairie Landing Golf Club, West Chicago
A classic Friday tradition with great food and a casual setting, running through early April.
March 28, 2026 – Saturday Highlights (DuPage)
Vivid Creatures – The Morton Arboretum, Lisle
Explore larger-than-life animal sculptures and immersive outdoor art installations set across scenic walking trails.Local Brewery Scene + Live Music Nights – Itasca / Naperville Area
Many DuPage breweries host weekend performances, making Saturday night perfect for casual outings with live entertainment.Downtown Naperville Weekend Scene
Shops, restaurants, and coffee spots stay lively on weekends, making it one of the best areas in DuPage for a walkable day out.
March 29, 2026 – Sunday Highlights (DuPage)
Sunday Funday Live Music – Church Street Brewing Company, Itasca
Wrap up the weekend with laid-back live music, drinks, and a relaxed Sunday crowd.DuPage Forest Preserve Activities – Multiple Locations
Take advantage of miles of scenic trails, nature walks, and peaceful outdoor spaces across the county.Local Events & Community Programming – Naperville & Wheaton
From museum programs to community activities, DuPage offers a variety of smaller local events and experiences happening throughout the weekend.
Weekend Wrap-Up
Whether you’re exploring Chicago’s vibrant theatre and museum scene or enjoying live music and outdoor experiences in DuPage, this weekend offers something for everyone. Take advantage of the city’s cultural events or discover hidden gems in the suburbs — either way, it’s a great weekend to get out and explore.
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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