Things to Do in Chicago and DuPage This Weekend

Things to Do in Chicago and DuPage This Weekend

Here’s your weekend guide to the best events and activities happening around Chicago and DuPage County from Friday, January 23 to Sunday, January 25, 2026 — from culinary celebrations and live performances to food crawls, markets, and cultural experiences!

January 23, 2026 – Friday Highlights (Chicago)

  • Chicago Restaurant Week – Various Restaurants Across the City
    - Chicago’s annual culinary celebration kicks off with prix‑fixe menus at hundreds of top restaurants. Enjoy special brunch, lunch, and dinner menus from celebrated chefs and neighborhood favorites.

  • Chicago Blackhawks vs. Tampa Bay Lightning – United Center
    - Get your hockey fix with an exciting NHL matchup under the bright lights at the iconic United Center.

  • ComedySportz Chicago – Local Comedy Venues
    - Laugh the night away with fast‑paced improv battles featuring Chicago’s top comedy teams.

  • Eureka Day – Broadway Playhouse at Water Tower Place
    - Catch this engaging, award‑winning play that dives into modern social themes in a smart, witty production.

  • Candlelight Concerts – Tribute Shows
    - Intimate live music concerts celebrating The Beatles, Adele, and more at venues around the city.

…plus plenty of bar shows, neighborhood dining tours, and winter city sights to explore.

 Read the full Chicago events calendar. 

January 24, 2026 – Saturday Highlights (Chicago)

  • Chicago Restaurant Week – Across the City
    - Continue exploring prix‑fixe menus and dining experiences at hundreds of participating restaurants during Restaurant Week.

  • Polar Adventure Days – Chicago Parks
    - Enjoy free family fun in Chicago’s parks with winter activities like sled dogs, snowshoeing, and crafts (South Loop).

  • Wrigleyville Mac & Cheese Crawl – Various Bars in Wrigleyville
    - A winter‑time culinary crawl featuring indulgent servings of mac & cheese paired with drink specials — fun for food lovers.

  • Disney On Ice: Jump In! – Allstate Arena, Rosemont
    - Perfect for families — this ice show brings beloved characters and thrilling performances to life on ice.

  • Maxwell Street Market – 800 S. Desplaines St.
    - Explore one of Chicago’s historic markets with eclectic vendors, street food, and cultural flair.

…plus immersive art exhibits, museum highlights, and local neighborhood activities.

 Discover more events this weekend. 

January 25, 2026 – Sunday Highlights (Chicago)

  • Musical Theatre Performances – Cadillac Palace Theatre & More
    - Catch world‑class musical theatre, including The Phantom of the Opera, Les Misérables, and Eureka Day at iconic stages across the city.

  • Lyric Opera of Chicago: Salome – Civic Opera House
    - Experience this dramatic opera masterpiece, a must‑see for classical music and theatre fans.

  • Kirill Gerstein Classical Concert – Symphony Center
    - Enjoy an afternoon of refined classical music featuring world‑class performance.

  • Disney On Ice (Matinee) – Allstate Arena
    - Another chance to catch this family‑friendly ice spectacular before the weekend ends.

…or explore Chicago’s vibrant brunch, shopping, or winter trail walks.

See all Chicago events

DuPage County Weekend Highlights (January 23–25, 2026)

Here are some ways to enjoy the western suburbs this weekend — including community shows, exhibits, and indoor activities:

  • DuPage County Fairgrounds Show – DuPage County Fairgrounds, Wheaton
    - Browse sports cards, trading cards, TCG collectibles, and more at this popular fairgrounds market show.

  • Visit the DuPage County Historical Museum – Wheaton
    - Explore thought‑provoking exhibits this January, like Tense Times: The Cold War in DuPage County and Woven Together: Coverlets and Community in DuPage.

  • Winter in DuPage Forest Preserves
    - Take a crisp nature walk, scenic hike, or picnic in preserved outdoor spaces like Waterfall Glen or Mayslake Peabody Estate — perfect for winter scenery and fresh air.

  • DuPage Children’s Museum Activities
    - Check for ongoing family‑friendly museum programs and exhibits (see local providers for exact times).

  • Charming Downtown Explorations
    - Stroll through historic downtowns in Naperville, Wheaton, Elmhurst, and Glen Ellyn to enjoy local cafés, boutiques, and seasonal winter activities.

Explore more DuPage events

Wrap‑Up

From Chicago Restaurant Week and Wrigleyville food crawls to musical theatre, opera, and winter markets, Chicago’s weekend from January 23–25, 2026, offers something for every interest. In the DuPage suburbs, local shows, museum exhibits, scenic preserves, and community markets make for a fun and fulfilling weekend as well.

Plan your weekend, explore the highlights, and make the most of winter fun across city and suburbs!

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Ranked as a top 1% team in the Chicagoland market, Cory Tanzer and the Cory Tanzer Group specialize in the Chicago, Western Suburbs, and Northshore 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.