Things to Do in Chicago and DuPage this Weekend (February 20–22, 2026)

Things to Do in Chicago and DuPage this Weekend (February 20–22, 2026)

Looking for the best events happening this weekend in and around Chicago? From theater premieres and immersive experiences in the city to food, live music, and family-friendly activities across DuPage County, here’s your curated weekend guide for February 20–22, 2026.

Chicago Weekend Highlights (February 20–22, 2026)

Friday, February 20, 2026 — Theater, Design, and Nightlife

The Architecture & Design Film Festival Chicago — Gene Siskel Film Center

- Running February 20 through February 22, this festival features films focused on architecture, urban design, sustainability, and creative innovation. Screenings take place at the Gene Siskel Film Center in the Loop, offering a strong cultural start to the weekend for design enthusiasts and anyone interested in how cities evolve.

Cut to the Chase — Chicago Theater Performance

- A longtime Chicago theater favorite, this production presents six short plays performed back-to-back as one program. The 90-minute show highlights world premieres and Chicago premieres, creating a fast-paced and intimate theater experience for Friday evening plans.

Before and After, an Instant Drama — Live Improvised Theater

- This performance explores life-changing moments through improvisational storytelling, meaning no two shows are the same. It’s a unique option for theatergoers looking for something spontaneous and engaging.

Voila: The Improvised Musical — iO Chicago

- A fully improvised musical performed live every Friday night. The show blends comedy, music, and audience energy, making it an easy late-night entertainment option in the city.

Saturday, February 21, 2026 — Culture and Performances

The Architecture & Design Film Festival Chicago — Continued Screenings

- Saturday continues the festival lineup with additional film screenings and programming centered around architecture and creative design. This event is ideal for anyone who enjoys urban culture, city planning, or visual storytelling.

Before and After, an Instant Drama — Additional Performances

- Saturday performances continue, giving weekend visitors another opportunity to experience this live, unscripted theater production.

Yoko Ono: Music of the Mind — Museum of Contemporary Art

- One of the largest exhibitions dedicated to Yoko Ono continues through February 22, making this weekend one of the final chances to experience the show. The exhibition explores her work across music, performance art, and activism.

Sunday, February 22, 2026 — Travel Inspiration and Weekend Wind Down

Final Day: Architecture & Design Film Festival Chicago

- Sunday wraps up the festival with its last round of screenings, offering a relaxed weekend wind-down for those looking to explore Chicago’s design and creative scene.

Final Day: Yoko Ono Exhibition at MCA Chicago

- Sunday is also the closing day for this major art exhibition, making it a strong cultural choice before the weekend ends.

DuPage County Weekend Highlights (February 20–22, 2026)

Friday, February 20, 2026 — Food and Live Music

Live Music at Arrowhead Restaurant & Bar — Wheaton

- A relaxed suburban option featuring live music and dining, perfect for starting the weekend without heading into the city.

Legally Blonde the Musical Jr. — Naperville

- This youth theater production begins its run with performances scheduled Friday evening, offering a fun and family-friendly option for local residents.

Arena Theater: Arms and the Man — Wheaton College

- A classic theatrical performance staged at Wheaton College, providing a strong arts option for suburban audiences.

Saturday, February 21, 2026 — Arts and Winter Experiences

Legally Blonde the Musical Jr. — Afternoon and Evening Shows

- Saturday features additional performances, making it a great option for families or anyone looking for local theater close to home.

Arena Theater: Arms and the Man — Evening Performance

- Saturday night continues the run of this classic stage production in Wheaton.

Discover DuPage Weekend Events Series

- Restaurants, arts venues, and local attractions across DuPage continue hosting weekend programming, with options ranging from live entertainment to community gatherings.

Sunday, February 22, 2026 — FAMILY-FRIENDLY and Community Events

• DuPage Weekend Events Wrap-Up

- Sunday offers a quieter pace across the suburbs, with ongoing exhibits, dining events, and family-friendly activities continuing through the weekend. It’s a good day to explore local museums, nature preserves, or casual dining experiences highlighted on the Discover DuPage calendar.

Weekend Wrap Up

This weekend brings a strong mix of experiences across both the city and suburbs. Chicago’s lineup leans into theater, design, and immersive events, while DuPage offers dining specials, live music, nature activities, and family-friendly programming. Whether you’re planning a full weekend itinerary or just looking for one great outing, February 20–22 offers plenty of reasons to get out and explore.

For more events, you can browse the official calendars from Choose Chicago and Discover DuPage for additional listings and updates.

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.