Things to Do in Chicago and DuPage This Weekend (Jan 30 – Feb 1, 2026)

Things to Do in Chicago and DuPage This Weekend (Jan 30 – Feb 1, 2026)

Whether you’re planning a night out in the city or a cozy adventure in the suburbs, this weekend offers a mix of events for every interest. From foodie fun to artistic performances and seasonal festivals, here’s what’s happening:


January 30, 2026 – Friday Highlights (Chicago)

  • The Infamous Stringdusters Live – Thalia Hall, 1807 S Allport St
    Enjoy a concert by this acclaimed progressive bluegrass band for a fun live music night.

  • Chicago January Glow Vendor Fair – The Geraghty, 2520 S Hoyne Ave
    Shop handmade goods, boutique crafts, and specialty finds from local vendors in a warm indoor market atmosphere.

  • SoxFest Live (Season Ticket Holder Night) – Ramova Theatre
    A winter fan celebration with live entertainment and player interactions; general admission events continue Saturday.

  • Live Jazz & Shows – Various Venues
    Catch jazz nights, percussion ensembles, or solo concerts at local venues like The Auditorium or Space Evanston.


January 31, 2026 – Saturday Highlights (Chicago)

  • SoxFest Live – Ramova Theatre & ComEd Rec Center
    General admission weekend festivities bring fan energy with interactive experiences and entertainment.

  • Ravenswood Makers Market – KOVAL Distillery, Ravenswood
    Browse a curated winter market featuring local artisans, makers, and unique gifts (free to attend).

  • Cider Summit Chicago – Navy Pier
    Sample hard ciders from around the world with tastings, food pairings, and a lively festival vibe.

  • Live Ice Sculpting – Various Locations (Free)
    Watch master ice carvers sculpt stunning works live — a fun, family‑friendly winter tradition.

  • The Annoyance Sketch Comedy – Annoyance Theatre, 851 W Belmont Ave
    Experience Chicago’s signature sketch comedy scene with a late‑night show.


February 1, 2026 – Sunday Highlights (Chicago)

  • The Phantom of the Opera – Cadillac Palace Theatre, 151 W Randolph St
    Catch the spectacular Broadway hit in the heart of the Loop.

  • Chicago International Puppet Theater Festival – Various Venues
    Enjoy puppet performances and family events — part of a fun citywide festival.

  • Chicago Boat Show – Donald E. Stephens Convention Center
    Explore boats, water sports gear, and interactive exhibits at this long‑running annual show.

  • Candlelight Concert Series – Classical Tribute Shows
    Soak in beautiful live music in candlelit settings, featuring tributes to favorite artists.



The suburbs are buzzing this weekend with seasonal festivals, artisan markets, and cozy experiences perfect for families and couples alike:


January 30, 2026 – Friday Highlights (DuPage)

  • Naperville Ale Fest – Naperville Riverwalk
    Sample craft beers from local and regional breweries while enjoying scenic downtown views.

  • Winter Hike – Waterfall Glen Forest Preserve, Darien
    Take a guided winter hike along scenic trails, perfect for outdoor enthusiasts of all ages.

  • DuPage Farmers Market – Wheaton
    Shop fresh local produce, baked goods, and artisanal products while supporting DuPage vendors.


January 31, 2026 – Saturday Highlights (DuPage)

  • Great Midwest Train Show – DuPage County Fairgrounds, Wheaton
    Browse hundreds of tables of model trains, collectibles, and accessories.

  • Chocolate Weekend – The Morton Arboretum, Lisle
    Savor artisan chocolates and cocoa-themed treats while strolling the winter grounds.

  • Forest Preserve Winter Hikes – McDowell Grove & Waterfall Glen
    Discover scenic trails, wildlife, and fresh winter air on guided or self-guided hikes.

  • DuPage Art League Workshop – Wheaton
    Participate in creative art workshops for beginners and experienced artists alike.


February 1, 2026 – Sunday Highlights (DuPage)

  • Great Midwest Train Show – DuPage County Fairgrounds, Wheaton
    Shop hundreds of tables of model trains, collectibles, and hobby supplies.

  • Chocolate Weekend – The Morton Arboretum, Lisle
    Indulge in chocolate tastings and cocoa-themed treats while enjoying the Arboretum grounds.

  • Forest Preserve Winter Hikes – Waterfall Glen & McDowell Grove
    Take in winter scenery and wildlife on guided or solo hikes through DuPage’s natural spaces.

  • Naperville Restaurant Week (ongoing)
    Dine at local favorites and enjoy special menus and deals throughout Naperville.



Wrap‑Up

From live music, foodie festivals, and fan celebrations in Chicago to seasonal winter festivals and artisan markets in DuPage, this weekend (January 30 – February 1, 2026) offers an exciting mix of activities for locals and visitors alike. Whether you’re looking for indoor entertainment, outdoor winter fun, tasty treats, or cultural experiences, there’s something to explore and enjoy!



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