Things to Do in Chicago and DuPage | Weekend Guide (February 27 – March 1, 2026)
Planning your weekend? Whether you’re heading into the city for live theatre, museums, and comedy or staying closer to the suburbs for live music and seasonal experiences, there are plenty of exciting events happening across Chicago and DuPage this weekend. Here’s your organized guide to help you plan.
CHICAGO WEEKEND HIGHLIGHTS
February 27, 2026 – Friday Highlights (Chicago)
Open Your Eyes: Chicago’s Underground Pedway Walking Tour – Inside Chicago Walking Tours
- Explore hidden underground passageways and discover secret stories of the Loop during this mostly indoor guided walking experience.By A Thread: Nature’s Resilience – Peggy Notebaert Nature Museum, 2430 N Cannon Dr
- Dive into biodiversity and conservation through engaging exhibits perfect for both adults and kids.Not a Soft Thing: A Group Exhibition by Artist Mothers – Chicago Cultural Center, 78 E Washington St
- A thought-provoking collection showcasing works by 15 artists exploring identity, caregiving, and culture.A Raisin in the Sun – Kennedy-King College Theater, 740 W 63rd St
- Experience Lorraine Hansberry’s iconic Chicago-based play brought to life on stage.American Prophets: Writers, Religion, and Culture – American Writers Museum, 180 N Michigan Ave
- Discover how spirituality and religion influenced American writers and culture.ComedySportz Chicago – Malarkey Comedy, 1501 N Kingsbury St
- Interactive improv comedy where performers compete for laughs in a fun, fast-paced show.The Infinite Wrench – Neo-Futurist Theater, 5153 N Ashland Ave
- Catch Chicago’s legendary late-night show featuring 30 short plays in 60 minutes.
February 28, 2026 – Saturday Highlights (Chicago)
By A Thread: Nature’s Resilience – Peggy Notebaert Nature Museum, 2430 N Cannon Dr
- Dive into science, conservation, and biodiversity through engaging museum exhibits.Uncertain Histories – Chicago Cultural Center, 78 E Washington St
- Explore historical narratives and stories connected to Chicago’s past through immersive displays.Not a Soft Thing: A Group Exhibition by Artist Mothers – Chicago Cultural Center
- A thought-provoking exhibition showcasing artists exploring motherhood, culture, and identity.Illinois Holocaust Museum Experience360 – 360 N State St
- A panoramic and educational exhibit encouraging reflection through stories of survival and history.North Side Restaurant Week – Various Locations
- Enjoy special menus and dining deals across multiple North Side neighborhoods.All That Glam: Chicago’s Art Deco Masterpieces Walking Tour – Inside Chicago Walking Tours
- Discover the glitz and architectural beauty of Chicago’s iconic Art Deco buildings.The Chinatown Adventure Food Tour – Triple Crown, 2217 S Wentworth Ave
- Taste authentic cuisine while learning about Chinatown’s culture and history.Black Makers Market – Navy Pier
- Shop local and support Black-owned brands, artists, and creatives in a vibrant marketplace.Monster Jam 2026 – Allstate Arena, 6920 Mannheim Rd
- High-energy monster truck action featuring massive vehicles and thrilling performances.Chicago Fire FC vs. CF Montreal – Soldier Field, 1410 Special Olympics Dr
- Catch exciting Major League Soccer action live in the South Loop.Blippi Live: Be Like Blippi Tour – The Chicago Theatre, 175 N State St
- A fun, interactive live show designed for younger audiences and families.The Addams Family Musical – Greenhouse Theater Center, 2257 N Lincoln Ave
- A hilarious and spooky musical celebrating the world’s quirkiest family.
March 1, 2026 – Sunday Highlights (Chicago)
Hubbard Street Dance Chicago: Winter Series – Harris Theater, 205 E Randolph St
- Experience an inspiring contemporary dance performance closing out the Winter Series.Chicago Bulls vs. Milwaukee Bucks – United Center, 1901 W Madison St
- Catch a major NBA matchup as the Bulls take on the Bucks.“Unicorn” Spinosaurus Unveiled! – Chicago Children’s Museum, 700 E Grand Ave
- Travel back millions of years with this exciting dinosaur exhibit perfect for families.Hamnet – The Yard at Chicago Shakespeare, 800 E Grand Ave
- A powerful theatrical story inspired by Shakespeare’s life and legacy.Miss Julie – Court Theatre, 5535 S Ellis Ave
- A classic drama exploring themes of class, power, and desire.The Addams Family Musical – Greenhouse Theater Center
- Enjoy this comedic musical packed with quirky characters and humor.Chicago Flamenco Festival 2026: Irene Morales RAW – Instituto Cervantes, 31 W Ohio St
- A bold flamenco performance blending tradition with contemporary expression.Goodbye Darkness, We’re Not Friends – Second City, 230 W North Ave
- A comedic show with dark humor and clever storytelling.HighQ – The Lincoln Lodge, 2040 N Milwaukee Ave
- An interactive comedy game-show experience combining theater and audience participation.
DUPAGE WEEKEND HIGHLIGHTS
Looking for something a little more relaxed this weekend? DuPage offers live music, seasonal experiences, and outdoor-friendly attractions perfect for families, couples, and casual weekend explorers.
February 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 local vibe.Vivid Creatures – The Morton Arboretum, Lisle
- Explore larger-than-life animal sculptures and art installations throughout the beautiful arboretum grounds.Winter Wonderland – Reserve 22, Village Links of Glen Ellyn
- Enjoy a cozy seasonal atmosphere with winter-themed décor and relaxing surroundings.
February 28, 2026 – Saturday Highlights (DuPage)
Saturday Night Live Music – Church Street Brewing Company, Itasca
- Another evening of live music and community energy in a casual setting.Vivid Creatures – The Morton Arboretum, Lisle
- Perfect for a scenic walk featuring art, nature, and outdoor exploration.Winter Wonderland – Reserve 22, Glen Ellyn
- A great weekend destination for seasonal fun and winter ambiance.
March 1, 2026 – Sunday Highlights (DuPage)
Sunday Funday Live Music – Church Street Brewing Company, Itasca
- Wrap up the weekend with live performances, good drinks, and laid-back Sunday vibes.Vivid Creatures – The Morton Arboretum, Lisle
- Enjoy one more stroll through this immersive outdoor art experience.Winter Wonderland – Reserve 22, Glen Ellyn
- A cozy way to end the weekend with family or friends.
Weekend Wrap Up
From Valentine’s fireworks and orchestra performances in Chicago to nature walks and suburban events in DuPage County, February 13 through 15 offers a well-balanced mix of city energy and neighborhood experiences.
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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