🥂 “Unlock Chicagoland’s Best-Kept Secrets!” 🍻🍷🍹
Looking for exciting things to do in Chicagoland? You won’t be disappointed! This week brings winter finales, cultural events, live shows, and cozy indoor activities all across the city. Check out our curated guide from January 23 to January 29, 2026 — there’s something for everyone to enjoy!
FRIDAY, January 23
📌 Chicago Restaurant Week Begins – Citywide All Day
Dive into Chicago’s 19th annual Restaurant Week, with prix-fixe brunch, lunch, and dinner menus at over 500 top restaurants across the city.
📌 Dry Cleaning Live – Thalia Hall @ Evening
Celebrating the start of their 2026 North American tour, British post-punk band Dry Cleaning plays Chicago tonight — a great way to kick off your weekend with edgy live music.
Evening Option:
Warm up with drinks and jazz at a cozy River North lounge or take a nighttime stroll toward the Chicago Riverwalk for skyline views.
SATURDAY, January 24
📌 Polar Adventure Day – Northerly Island @ All Day
Embrace the winter outdoors with husky sled demos, snowshoeing, crafts, bonfires, and hot cocoa at this beloved winter tradition just steps from the Museum Campus. (Event details shared annually by Chicago Park District — search Chicago Park District events for times and registration.)
📌 Chicago Winter Whiskey Tasting Festival – Downtown @ Afternoon/Early Evening
Sip and sample over 20 premium whiskies, meet brand experts, and enjoy music and mingling at this indoor winter festival. (Ticket & festival info typically listed on event ticketing platforms and social channels near the event date.)
Bonus / Daytime Idea:
Take advantage of free museum admission today — Shedd Aquarium and museums around the city offer perks for Illinois residents.
SUNDAY, January 25
📌 Jean Banchet Awards Ceremony – Venue SIX10 @ Evening
Celebrate Chicago’s culinary excellence with the Jean Banchet Awards, honoring the city’s finest chefs and restaurants in a delicious evening of recognition and fun.
📌 Amadeus at Steppenwolf Theatre – Through Evening
See the acclaimed musical drama Amadeus, running through late January — a perfect cultural afternoon or evening out.
Relax & Explore:
Glide around the McCormick Tribune Ice Rink in Millennium Park — winter skating is still in full swing through the end of the month.
MONDAY, January 26
📌 Free Museum Days – Various Chicago Museums
Take advantage of free admission days: Field Museum, Adler Planetarium, Museum of Science and Industry, and more offer opportunities to explore world-class exhibits without breaking the bank.
Evening Option:
Continue Restaurant Week with a prix-fixe dinner at a neighborhood favorite or catch a midweek improv or stand-up comedy show.
TUESDAY, January 27
📌 Shedd Aquarium Free Admission – All Day (Illinois Residents)
Illinois residents can enjoy free admission at the Shedd Aquarium — a perfect indoor escape for families and visitors alike.
📌 Chicago International Puppet Theater Festival – Ongoing Shows
Catch imaginative puppetry performances around the city as part of the long-running Puppetry Festival (runs Jan. 21–Feb. 1).
Evening Option:
Head to The Salt Shed for live music, DJs, or creative events (venue hosts diverse winter programming).
WEDNESDAY, January 28
📌 Adler Planetarium Free Night – 4:00 PM – 10:00 PM
Stargaze and enjoy astronomy exhibits with free admission for Illinois residents — ideal for a midweek night out.
Evening Option:
Sip cocktails at a cozy rooftop lounge or enjoy an intimate jazz show at a historic club like the Green Mill.
THURSDAY, January 29
📌 Chicago Boat Show – Donald E. Stephens Convention Center @ 11:00 AM – 8:00 PM
Explore this annual signature event with kayaks, yachts, outdoor gear, and travel inspiration — it’s perfect for planning summer’s next adventure.
📌 Lyric Opera of Chicago: Salome – Evening Performance
Experience the dramatic and intense opera Salome at the iconic Lyric Opera House — a thrilling night of world-class performance.
Daytime Option:
Take a mellow walk along the Bloomingdale Trail (The 606) for fresh air and urban views — Chicago’s elevated greenway is open year-round.
📌 Don’t Miss These Ongoing Events
🍽 Chicago Restaurant Week (Jan. 23 – Feb. 8) — Special prix-fixe meals for brunch, lunch & dinner at 500+ local eateries.
🎠Chicago International Puppet Theater Festival (Jan. 21 – Feb. 1) — Dozens of puppetry shows at venues citywide.
⛸ Ice Skating Rinks — Millennium Park and Maggie Daley Park continue outdoor skating all month.
🏛 Free Museum Days — Museums offer free entry on select days this month for Illinois residents.
✨ Embrace the heart of winter in Chicagoland! From culinary celebrations to music, theater, outdoor adventures, and free cultural excursions — there’s plenty to fill your week. Sign up for weekly updates to stay ahead of all the city’s best events and hidden gems!
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