aiplannerchicago events & things to do in january
Exciting events and experiences happening this month in Chicago.
Everyone's Hungover
Event Information
21+ / Free
Ticket Information
Check venue for pricing
Weed Passport Tours: North Michigan Ave Experience
Event Information
Weed Passport Tours: Chicago 🌆🍃 Walk. Chill. Explore. Discover Chicago’s vibrant North Michigan Ave like never before — through the lens of cannabis culture, art, and relaxation. Our guided Weed Passport Tour takes you on a scenic walk through iconic stops including premium dispensaries, local art landmarks, the Chicago Riverwalk, and chill zones by the lake. ✅ Exclusive dispensary discounts ✅ Local art + culture highlights ✅ Meet fellow cannabis travelers ✅ Perfect for tourists and locals alike 🎟️ Get your Weed Passport, explore the Magnificent Mile, and unlock a new kind of high-end Chicago experience. 📍 Start Location: Cookies Chicago, 215 N Clinton St, Chicago, IL 60661 (Outside Store) (“Exact meet-up instructions sent after booking.”) 🕒 Tour Time: Approx. 1.5 hours walking 🎫 Book your tour today #WeedPassportTours #ChicagoCannabis #WeedCulture #NorthMichiganAve #420Friendly #ChicagoTours #CannabisTravel
Ticket Information
Check venue for pricing
Chicago Blackhawks vs. Dallas Stars
Accessibility Information
ADA seating for patrons with wheelchairs and their companions is available for all Chicago Blackhawks events. Guests may purchase one wheelchair accessible seat and one companion seat. If you have questions or desire further information, please contact the Box Office at (312)455-4655.
Ticket Information
Check venue for pricing
UIC Flames Men's Basketball v Murray State
Accessibility Information
ADA seating for patrons and their companions is available for all UIC Pavilion events. Accessible seating locations will vary per event. Accessible seating is limited and is sold on a first come first served basis. There is a ticket limit of four per purchase for all ADA and companion seating. If you have questions or desire further information, please contact the Box Office at 312-413-5740.
Ticket Information
Check venue for pricing
Light of Christmas Drive Thru
Event Information
Chicago's Drive Thru Light Show at White Sox Park @ Rate Field
Ticket Information
Check venue for pricing
Santa's Treehouse 🎅🏻
Event Information
Welcome to The Naughty North Pole—Chicago’s cheekiest winter hideaway, where snowflakes sparkle, cocoa gets spiked, and every corner is brimming with holiday mischief. This year, the Treehouse is bigger, bolder, and naughtier than ever—cozy corners, whimsical bites, and cocktails so tempting they should be on Santa’s “naughty” list. 🍸 Ready to sip, snack, and misbehave? Reserve your table through OpenTable (recommended) — Claim your spot in Santa’s secret hideaway. Sip flirty cocktails, snack on treats even the elves envy, and pose in over-the-top holiday décor designed for maximum mischief. Perfect for cheeky date nights, rowdy friend squads, or anyone feeling a little naughty & nice. 🎅 Just here to roam… and get caught under the mistletoe? No reservation? No problem! Grab a ticket and explore the Treehouse at your own pace. Sip spiked cocoa, sneak into hidden corners made for trouble, and get lost in the twinkle—and the filthy fun—of Christmas mischief. (General admission does not include reserved seating.) 🧝 Family-friendly til 8pm — After that, the lights dim, the music cranks, and the holiday spirit gets extra playful. Whether you’re here to toast the season, stir up some mischief, or just revel in a little winter magic, The Naughty North Pole is calling. Bring your elves, your besties, or come solo—because even Santa loves a secret adventure!
Ticket Information
Check venue for pricing
New Year's Day | Rino Bar
Event Information
RINO BAR in River North $10 Yardsticks 11pm - 12am $7 Shots ALL NIGHT 2 x 500 Premium House Tequila AGES: 21+ w/ valid physical ID The only IDs that are accepted for entrance are the following in physical form only: • USA government issued drivers license and identification cards • ANY government issued passport Food: Pizza served all night Dress Code: Upscale and Stylish Nightlife attire. Ladies aim for elegance and style. Heels or stylish flats are great choices. Avoid overly casual wear like gym clothes or flip-flops. Look great while staying comfortable. Gentlemen aim for clean and confident looks. Dress shoes or trendy sneakers work well. Avoid overly casual attire like athletic wear. Maintain a polished appearance for the night. Payment Made Easy Tickets are available at the door. We accept Cash, Debit, and Credit! Tickets are non-refundable under any circumstances. Refunds will solely be processed in the event of an event cancellation. Alternatively, you have the option to acquire insurance at the point of purchase for added protection. Where: RINO BAR (Directions) 642 N Clark St, Chicago, IL 60654 View Full Bottle Menu Here
Ticket Information
Check venue for pricing
The Chicago Theatre Tour Experience
Ticket Information
Check venue for pricing
The Hoyle Brothers - Live and on the Big Stage!
Event Information
FREE // 21+Hoyle Brothers Live and on the Big Stage for 4 and a half hours!
Ticket Information
Check venue for pricing
Iris Blue w/ Matt Sandelin
Ticket Information
Check venue for pricing
The Phantom of the Opera (Chicago)
Accessibility Information
Wheelchair and companion seating available. For more information please call (312) 977-1701 ext. 1259.
Ticket Information
Check venue for pricing
Chicago Bulls vs. Orlando Magic
Accessibility Information
ADA seating for patrons with wheelchairs, or hearing imparied and their companions is available for all Chicago Bulls events. Guests may purchase one accessible seat and one companion seat. If you have questions or desire further information, please contact the Box Office at (312)455-4655.
Ticket Information
Check venue for pricing
Ready to Experience Chicago?
Plan your perfect itinerary around these amazing events
Use our AI planner to create a personalized Chicago itinerary for January 2026. Chat with our AI assistant to get recommendations for hotels, restaurants, and activities that complement these events. Our intelligent trip planner considers your preferences, budget, and travel dates to create the perfect Chicago travel plan. Features include real-time weather updates, interactive maps, and local insider tips.
