Things to Do in Chicago and DuPage This Weekend

Whether you’re into theatre, family fun, exhibits, or seasonal activities, Chicago is buzzing with events and experiences this coming weekend that are perfect for locals and visitors alike.

Chicago Events – January 16–18, 2026

January 15, 2026 – Thursday Highlights

• The Phantom of the Opera – Cadillac Palace Theatre, 151 W. Randolph St.
  Catch this beloved musical spectacle as it continues its run in downtown Chicago.

• Eureka Day – Broadway Playhouse at Water Tower Place, 175 E. Chestnut St.
  See this acclaimed play from TimeLine Theatre Company at a central Loop theatre.

• Balloon Museum: EmotionAir – The Fields Studios – Gate 1, 2828 N. Pulaski
  Enjoy another day of immersive balloon art and participatory exhibits.

• Filament Theatre presents RAIN: for babies and their carers – 4041 N. Milwaukee Ave.
  A creative performance designed specifically for very young audiences and their caregivers.

• By A Thread: Nature’s Resilience – Peggy Notebaert Nature Museum, 2430 N. Cannon Dr.
  Dive into biodiversity and conservation science through engaging displays.

• Not a Soft Thing: A Group Exhibition by Artist Mothers – Chicago Cultural Center, 78 E. Washington St.
  Explore multidisciplinary works that reflect motherhood and identity.

• Museum of Ice Cream’s Pinkmas – 435 N Michigan Ave Suite G
  A colorful, seasonal celebration with interactive exhibits.

• McCormick Tribune Ice Rink – Millennium Park, 201 E Randolph St.
  Ice skating with skyline views (weather-permitting).

…plus river architecture tours, tasting experiences, and more!

Read more about all Chicago events. 

January 16–18, 2026 – Mid-Week Special Events

Chicago Cubs Convention (Jan 16–18) – Sheraton Grand Chicago, 301 E North Water St.
Three full days dedicated to Cubs fans, celebrating the franchise’s history (including the 10-year anniversary of the 2016 World Series team), panel discussions, memorabilia, and interactive fan experiences.

• Opening Ceremonies traditionally begin in the early evening on Friday.

• Various panels, autograph opportunities, and activities run through Sunday.

This is a must-attend event for baseball fans and a unique Chicago winter weekend experience.

January 17, 2026 – Saturday Highlights

• Brian Regan Live – Chicago Theatre, 175 N. State St.
  Laugh out loud with one of the most popular stand-up comedians; a top pick for comedy lovers.

• Kids Meet the Music (D-Composed Ensemble + Josh Jones) – Harris Theatre, Millennium Park
  A family-friendly musical experience celebrating rhythmic and percussive sounds in music.

• Pilates at The Auditorium – Auditorium Theatre, 50 E Ida B Wells Dr.
  Start your weekend with movement and mindfulness at one of Chicago’s landmark venues.

• Chicago Architecture Biennial Exhibits (ongoing)
  Explore one of the largest global architecture and design exhibitions featuring works from around the world — free in many venues through late February.

More autumn/winter events across Chicago. 

January 18, 2026 – Sunday Highlights

• Krampus: The Fright Before Christmas – 13th Floor Chicago, 5050 River Rd.
  A seasonal attraction with a spooky twist (continuing holiday fun).

• Wheel of Improv – The Second City, 1616 N. Wells St.
  Comedy night with performers competing for laughs and audience interaction.

…plus ongoing Chicago Cultural Center and Peggy Notebaert Nature Museum exhibits.

Read more about all Chicago events. 

DuPage County Events – January 16–18, 2026

Looking for fun and engaging activities in DuPage County this weekend? From festivals and outdoor nature spots to music and community experiences, the western Chicago suburbs have something for everyone. Explore local highlights below!

January 16, 2026 – Friday Highlights

While there are no specific events listed for Friday on the official DuPage events calendar for this date, DuPage offers plenty of ongoing experiences perfect for evening plans or start-of-weekend outings:

• Explore Forest Preserves & Trails – DuPage’s expansive preserves like Waterfall Glen offer scenic winter hikes and peaceful nature walks, ideal for fresh air and photos.

• Charming Downtowns & Shopping – Visit Wheaton, Naperville, Elmhurst, or Lombard for boutique shopping, local cafés, and dinner spots.

• Local Museums & History – The DuPage County Historical Museum in Wheaton showcases regional heritage and is a relaxed stop for history buffs.

…plus keep an eye out for indoor concerts, trivia nights, or community center activities posted locally!

Read more about all DuPage events.

January 17, 2026 – Saturday Highlights

Illinois Vintage Fest – DuPage County Fairgrounds, 2015 Manchester Rd, Wheaton
Browse 100+ vintage vendors featuring clothing, collectibles, home goods, and more at this popular seasonal festival running both Saturday and Sunday. Admission is free!

Nature & Outdoors

• Take advantage of DuPage’s forest preserves (like Waterfall Glen) for winter hikes and scenic views.

• Visit nearby Cosley Zoo in Wheaton — a fun, smaller zoo with both domestic and native animals (great for families).

Charming Downtown Explorations

• Explore local shops and eateries in Naperville, Elmhurst, or Glen Ellyn, each offering unique experiences and seasonal specials.

Ongoing Cultural Sites:

• Stop by the DuPage County Historical Museum for local history exhibits.

Read more about all DuPage events.

January 18, 2026 – Sunday Highlights

Illinois Vintage Fest – DuPage County Fairgrounds, Wheaton
Enjoy the second day of this popular vintage festival with vendors, collectibles, and unique finds across multiple buildings.

Live Music & Cultural Spots

• While specific concerts or performances aren’t listed for this exact date in DuPage’s calendar, many local venues, restaurants, and community centers often host live music, brunch gigs, or open mic events — check local social pages or park district calendars.

Explore Nature & Museums

• Continue exploring forest preserve trails or family-friendly indoor exhibits.

• Visit Wheaton’s DuPage County Historical Museum or local art galleries for a leisurely afternoon.

Read more about all DuPage events.

More Things to Do in DuPage (All Weekend)

• Forest Preserve District Trails: Enjoy winter hikes and tranquil outdoor spaces in preserves like Waterfall Glen.

• Downtown District Walks: Wheaton, Naperville, Elmhurst, and Lombard are walkable downtowns with shops and cafés to explore.

• Local Museums & History: The DuPage County Historical Museum offers charming exhibits and context for regional history.

Final Tips for Your DuPage Weekend

• Dress warmly — January in DuPage can be chilly, especially for outdoor activities like hikes or browsing vendor fairs.

• Check local venue calendars for last-minute listings like trivia nights, brewery events, or winter pop-ups.

• Combine indoor and outdoor plans for a full weekend experience, mixing cultural visits with scenic walks and local food stops.

Stay Connected

Ranked as a top 1% team in the Chicagoland market, Cory Tanzer and the Cory Tanzer Group specialize in the Chicago, North Shore, and Western Suburbs real estate market. With deep local market expertise and a proven track record, Cory and his team help clients buy and sell with clarity, confidence, and results.