🥂 “Unlock Chicagoland’s Best-Kept Secrets!” 🍻🍷🍹
Looking for exciting things to do in Chicagoland? You won’t be disappointed! This week brings wintrier highlights, cultural events, live shows, and cozy indoor activities all across the city. Check out our curated guide from January 16 to January 22, 2026 — there’s something for everyone to enjoy!
FRIDAY, January 16
📌 2026 Chicago Cubs Convention – Sheraton Grand Chicago @ 6:30 PM – 10:30 PM
Kick off the weekend with Cubs fan festivities — meet legends, catch panels, celebrations, and unique fan activities at this annual event (runs through Jan. 18).
Evening Option:
Warm up at a cozy Chicago jazz club or bar with live music and seasonal cocktails.
SATURDAY, January 17
📌 Brian Regan Live – Chicago Theatre @ 7:00 PM
Laugh out loud with this celebrated stand-up comic delivering witty takes on everyday life in a highly anticipated comedy performance.
Bonus / Daytime Idea:
Try Pilates at the Auditorium in the morning — a unique wellness experience at the historic Auditorium Theatre.
SUNDAY, January 18
📌 Chicago Cubs Convention – Day 3 @ Sheraton Grand Chicago
Wrap up this fan-favorite weekend gathering with more meet-ups, panels, activities, and photos with Cubs greats.
Relax & Explore:
Warm up with brunch in Lincoln Park or check out indoor art installations at the Chicago Cultural Center.
MONDAY, January 19
📌 Martin Luther King Jr. Day Celebrations – Across Chicago
Honor the legacy of Dr. King at family-friendly events and community programs throughout the city celebrating civil rights and civic engagement. (Multiple community event listings available — check local community calendars for updated programming.)
📌 Crafting Character: The Costumes of Paul Tazewell – Griffin Museum of Science and Industry @ 10:00 AM & 12:00 PM
Explore this immersive exhibition highlighting the artistry behind iconic stage and screen costumes. (Check MSI Chicago official site/events schedule for details.)
Evening Option:
Attend a reflective panel, lecture, or community event focused on service and empowerment.
TUESDAY, January 20
📌 Free Museum Days & Adler Planetarium – Various Times
Illinois residents can enjoy free admission at Shedd Aquarium through Jan. 20, and Adler Planetarium offers free Wednesday nights — perfect for escaping the chill. (Check each institution’s admission schedule for exact times and eligibility.)
Evening Option:
Dive into the Chicago International Puppet Theater Festival opening events and intimate shows across the city (runs Jan. 21–Feb. 1).
WEDNESDAY, January 21
📌 Chicago International Puppet Theater Festival – Various Venues
Enjoy this imaginative festival showcasing puppetry arts with performances for all ages in venues around town.
Evening Option:
Head out for a candlelit classical concert or a symphony performance at Symphony Center to warm up mid-week.
THURSDAY, January 22
📌 First Bites Bash – Field Museum @ 7:00 PM
Kick off Chicago Restaurant Week early with this all-inclusive tasting event, a must for food lovers eager to sample the city’s top culinary talents.
Evening Option:
Catch a theater show like Amadeus at Steppenwolf Theatre or Stars & Garters After Dark for a lively night out.
📌 Don’t Miss These Ongoing Events
🎠Chicago International Puppet Theater Festival (Jan. 21 – Feb. 1) — Puppetry shows across dozens of venues with diverse performances.
🎨 Yoko Ono: Music of the Mind – MCA Chicago (through Feb. 22) — Explore this expansive retrospective of Yoko Ono’s influential work.
⛸ Ice Skating Rinks All Month — Outdoor skating at Millennium Park and Maggie Daley Park remains open through late January.
🏛 Free Museum Opportunities — Enjoy museum admission perks for Illinois residents throughout January at several major Chicago institutions.
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