Things to Do in Chicago and DuPage – Weekend Guide (March 20 – March 22, 2026)
Spring is starting to show up across Chicago, and this weekend is packed with events worth planning around. From immersive festivals and theatre to food tours and live entertainment, something is happening in every corner of the city and suburbs.
CHICAGO WEEKEND HIGHLIGHTS
March 20, 2026 – Friday Highlights (Chicago)
Glow Wild Lantern Festival – Chicago Area
Step into a glowing nighttime experience featuring illuminated lanterns inspired by wildlife and global cultures. A perfect date-night or family-friendly evening.The Brief Wondrous Life of Oscar Wao – Goodman Theatre
Catch a powerful stage adaptation of the award-winning novel brought to life at one of Chicago’s premier theatres.Hamilton – CIBC Theatre
Experience one of Broadway’s biggest hits with unforgettable music and storytelling about American history.ComedySportz Chicago – Malarkey Comedy, 1501 N Kingsbury St
Fast-paced improv comedy where teams compete for laughs in a fun, interactive format.Live Music Shows – Various Chicago Venues
From indie bands to touring artists, Chicago’s music scene is active across venues like House of Blues and Subterranean.
March 21, 2026 – Saturday Highlights (Chicago)
Villain Arts Chicago Tattoo Festival – Convention Venue
One of the biggest tattoo events of the year featuring top artists, live demonstrations, and competitions.Spring Festival of New Plays and Musicals – Chicago Theatres
Discover emerging theatre productions and original performances from up-and-coming playwrights.Chicago Food Tours – Various Neighborhoods
Explore the city’s food scene through guided tours featuring deep-dish pizza, local favorites, and cultural cuisine experiences.Candlelight Concerts – Various Venues
Enjoy live music performances in intimate, candlelit settings across the city.Museum & Exhibit Experiences – Citywide
Chicago’s museums continue to feature rotating exhibits and interactive experiences perfect for a Saturday outing.
March 22, 2026 – Sunday Highlights (Chicago)
Spring Festival of New Plays and Musicals (Final Shows)
Catch the final performances of new and experimental theatre productions before they close.Architecture River Cruises & Walking Tours
As temperatures begin to rise, architecture tours offer a great way to explore Chicago’s iconic skyline and design history.Live Theatre & Comedy Shows – Various Venues
From improv to dramatic productions, Chicago’s theatre scene continues strong through the weekend.Citywide Dining & Brunch Experiences
Wrap up the weekend exploring Chicago’s restaurant scene, with brunch, cafes, and local hotspots open across neighborhoods.
DUPAGE WEEKEND HIGHLIGHTS
Looking to stay closer to home? DuPage offers a more relaxed but still engaging weekend with nature experiences, local events, and live entertainment.
March 20, 2026 – Friday Highlights (DuPage)
Friday Night Live Music – Local Breweries & Venues
Enjoy live music paired with craft beer and a laid-back suburban atmosphere.Evening Nature Walks – DuPage Forest Preserves
Take advantage of early spring evenings with scenic trails and peaceful outdoor settings.
March 21, 2026 – Saturday Highlights (DuPage)
Springtime Outdoor Exploration – Morton Arboretum & Local Preserves
Explore trails, seasonal changes, and nature exhibits as spring begins to emerge.Downtown Naperville & Wheaton Shopping + Dining
Spend the day browsing boutiques, coffee shops, and local restaurants in DuPage’s walkable downtown areas.
March 22, 2026 – Sunday Highlights (DuPage)
Sunday Funday Live Music – Local Breweries
Wrap up the weekend with relaxed live performances and community vibes.Family-Friendly Activities & Local Events – DuPage County
From indoor play spaces to community events, there are plenty of ways to enjoy a laid-back Sunday.
Weekend Wrap-Up
From immersive festivals like Glow Wild and major theatre productions to local music and outdoor experiences in DuPage, this weekend offers a well-balanced mix of city energy and suburban relaxation. Whether you’re exploring downtown Chicago or staying closer to home, there’s no shortage of ways to make the most of your weekend.
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.
Stay Connected
Ranked among the top 1 percent of real estate teams in the Chicagoland market, Cory Tanzer and the Cory Tanzer Group are experts in helping buyers and sellers navigate today’s market across Downtown Chicago, the North Shore, and the Western Suburbs. Recognized for their neighborhood expertise in areas like University Village, University Commons, South Loop, and Pilsen, the team helps clients stay one step ahead by understanding where the Chicago market is moving next.
