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The Best Things to Do in Chicago This December 2025
Dec
Holiday Events, Festive Activities, and Places to Shop in the Windy City
Chicago in December is pure magic. The city transforms into a sparkling winter playground filled with twinkling lights, bustling holiday markets, cozy pop-ups, and plenty of places to shop for gifts (or treat yourself). Whether you’re local or visiting for the holidays, December is one of the best times to explore the city.
If you’re planning your holiday calendar, here are some of the most popular things to do in Chicago during December 2025 — plus one unique shopping stop that should be on your list.
🎄 1. Wander Through Christkindlmarket
Daley Plaza & Wrigleyville
Chicago wouldn’t be Chicago without Christkindlmarket. Sip hot wine, browse handmade gifts, snack on roasted nuts, and soak up all the cozy vibes you can handle. It’s busy, chaotic, and absolutely worth it.
Tip: Go early on weekday afternoons to avoid crowds.
⛸️ 2. Ice Skating at Millennium Park
Nothing beats skating with holiday lights around you and the skyline above you. Lace up at the iconic rink near Cloud Gate (aka “The Bean”), glide around to holiday music, and grab hot chocolate after.
It’s free! — you just need to reserve a time slot.
✨ 3. Light Up the Lake at Navy Pier
This winter indoor festival includes rides, ice skating, light installations, cocktails, games, and more. Perfect for families, dates, or honestly just staying warm while doing something festive.
They go big every year — expect photo ops everywhere.
🎁 4. Holiday Shopping Along the Magnificent Mile
Michigan Avenue goes all-out for the holiday season. Luxury stores, iconic brands, massive decorations, and plenty of deals make this a go-to stop for holiday shopping.
Even if you’re not planning a spree, the lights alone are worth the walk.
🐧 5. ZooLights at Lincoln Park Zoo
Lincoln Park Zoo transforms into a glowing wonderland every December. Think huge light displays, festive music, hot drinks, plus the added bonus of adorable animals.
Perfect for families, dates, or a low-pressure holiday night out.
🧤 6. Explore Local Boutiques and Small Businesses
Chicago neighborhoods thrive during the holidays, especially areas like:
Wicker Park
Roscoe Village
Andersonville
Logan Square
West Loop
Lincoln Park
Lakeview
Pilsen
You’ll find one-of-a-kind gifts, handmade goods, and festive pop-ups on just about every block. Supporting local is the Chicago way — and you’ll definitely discover something special.
💎 7. Shop, Gift, and Get Pierced at Identity Body Piercing
Wicker Park + Roscoe Village
Looking for a gift that actually feels personal, stylish, and memorable? Skip the socks and gift cards to big box stores — and give the gift of jewelry or a piercing experience instead.
Identity Body Piercing is Chicago’s go-to destination for premium body jewelry, curated ear styling, and safe professional piercing. It’s the perfect holiday stop for those shopping for:
Unique fine jewelry
Ear stacking projects
Quality titanium or gold pieces
New piercings
Memorable experiences
Accessories and aftercare
Not sure what someone would love?
We offer Identity Body Piercing gift cards, which can be used for:
Piercing appointments
Jewelry upgrades
Ear styling sessions
Accessories and aftercare
Online or in-studio shopping
Plus — every online order comes with complimentary gift wrapping and worldwide shipping, so gifting is easy no matter where you live. Orders +$100 ship free!
If you’re visiting Chicago in December, stop by:
✨ Wicker Park – 1514 N Ashland Ave Chicago, IL 60622
✨ Roscoe Village – 2256 W Belmont Ave Chicago, IL 60618
Walk-ins welcome daily for jewelry shopping and piercings.
Or shop online anytime at IdentityBodyPiercing.com
☕ 8. Holiday Pop-Up Bars Around the City
Chicago embraces holiday kitsch like no other city. December pop-ups are a staple, with themed cocktails, over-the-top décor, and cheesy music that’s impossible not to enjoy.
Popular spots return year after year — think Miracle Bar, Frosty’s, Rudolph’s Bar at Lost Never Found, and local one-offs popping up across the city.
Grab a drink, snap a photo, and get into the chaotic holiday spirit.
🌃 9. The Chicago Theatre, Broadway, and Live Shows
From holiday classics to comedy shows and touring Broadway productions, Chicago’s December performing arts scene is fully booked.
Treat yourself to a night out — it’s the ultimate cozy winter activity.
🎊 10. New Year’s Eve Fireworks and Events
Ring in 2026 with fireworks along the river, rooftop parties, or neighborhood celebrations. Chicago goes big for New Year’s Eve — so expect crowds, sparkles, and champagne.
❄️ Celebrate December in Chicago
Whether you love holiday lights, shopping, cozy drinks, or winter adventures, December in Chicago delivers. The city comes alive with festive events, local businesses, and endless things to do.
And while you’re out exploring, make sure to treat yourself (or someone else) to something special — whether that’s a beautiful piece of jewelry, a new piercing, or a gift card to Identity Body Piercing that will last long after the holidays are over.
Happy Holidays, Chicago!
Stay warm, shop local, and have fun out there.