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Published October 25, 2023
Chicago's Ultimate 2023 Winter Bucket List
The temperatures may be dropping, but the winter activities in Chicago are just starting to heat up. Check out this year's ultimate winter bucket list. ☃️ ❄️
by Chicago Bucket List
Chicago is a year-round city—which means the fun doesn’t stop when the weather gets colder. And the weather does get colder. As much as you may want to hole up and hibernate for five months out of the year, we're here to tell you not to do that.
Despite the cold, the city comes alive with enchanting twinkling lights and giant Christmas trees. Restaurant patios turn into winter wonderlands with heated igloos, Wrigley Field turns into an ice skating rink, and the CTA trains turn into a magical experience for the whole family. We rounded up all the best things to do in Chicago this winter, so invest in a good coat and lean into it.
The Best Things to Do in Chicago This Winter
Visit the Jack Frost Christmas Pop-Up at Fulton Market
This Winter Wonderland in Fulton Market is a must-visit. Stop by during the day for ice skating, winter bumper cars, axe throwing, Christmas Pop-Up Shops, and photo ops. Then indulge in boozy hot cocoa, seasonal cocktails, and explore a Christmas tree walk all lit up in the evenings. It's the ultimate Christmas experience for making memories with loved ones this season!
Where: 170 N Green St., Chicago, IL
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See the Millennium Park Christmas Tree
Chicago locals know the Millennium Park Christmas Tree gives the Rockefeller Plaza one a run for its money! The 110th tree lighting at Millennium Park will take place on November 17, following a special event, but you can stop by anytime through January 7 to see its thousands of gorgeous lights!
Where: Millennium Park: 201 E. Randolph St. Chicago, IL
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Grab a Drink at Frosty's Christmas Bar
Chicago's most festive holiday pop-up bar returns on November 18 and will be open all season long with all of the holiday cheer and shenanigans we've come to know and love. Bursting at the seams with over-the-top lights and decor, Frosty's will have life-size toy soldiers, roaming Santas and elves, and non-stop holiday music spinning across four bars, three levels, and two dance floors! And, of course, lots of specialty drinks and themed cocktails.
Where: Frosty's Christmas Bar: 809 W Evergreen Ave, Chicago, IL
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Drive Through World of Illumination
Step into a mesmerizing holiday wonderland at World of Illumination with six enchanting drive-through adventures! Round up the crew and embark on a light show extravaganza featuring tunnels, mega tower displays, and a symphony of over 16 million shades of color—all meticulously synchronized to a curated playlist that'll have the whole family dancing in their seats. Open through December 31!
Where: Six Flags Great America: 1 Great America Pkwy, Gurnee, IL
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Watch Nutcracker! Magical Christmas Ballet
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Ride The CTA Holiday Train
All aboard! Don’t miss out on one of Chicago’s most unique holiday traditions. Every year, beginning in early December, the CTA decks out trains and buses to spread magic and joy to families and to deliver food baskets to charitable agencies around the city.
Where: Various locations
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Go Ice Skating At Maggie Daley Ribbon
Ice skating is a pretty typical winter activity, but Maggie Daley Ribbon is not your typical ice rink. Lace up a pair of skates and glide along the winding skate path with breathtaking views of the Chicago skyline lighting the way in front of you. There’s no more perfect outing for family fun or a romantic date night out!
Where: 337 E Randolph St, Chicago, IL
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Watch the Chicago Blackhawks Play
Rally the crew and cheer on the Chicago Blackhawks as they tear up the ice during their annual Home for the Holidays series. Along with an action-packed hockey game, arrive early so you can enjoy the decorated United Center Atrium pregame with festive photo ops, a giant Christmas tree, light shows, take a photo with Santa, indulge in hot chocolate & cookies, and more. Whether it’s your first game or you’re a lifelong fan, an evening spent watching the Chicago Blackhawks during the holiday season is always a good time.
Upcoming games: December 9-10, 17, 19, 22 and 27.
Where: United Center: 1901 West Madison Street, Chicago, IL
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Make DIY Holiday Ornaments
Decorate your tree with custom DIY ornaments this year! No need to run to the craft store—head to Paradise Park, where you'll be provided with all the necessary supplies to make alcohol ink ornaments, disco mushrooms, or painted ornaments. Plus, you can enjoy bottomless house red, white, and rosé wine while you do it! It makes for a great indoor holiday activity or date night, and you'll leave with a pretty new decoration for your tree.
Where: Paradise Park: 1913 W. North Ave. Chicago, IL
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Spend an Evening at the Nutcracker Christmas Pop-Up Bar & Hotel
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Step into a world of timeless festive decor and classic holiday tunes at the Nutcracker Christmas Pop-Up Bar and Hotel. Enjoy Craft Christmas Cocktails, Charcuterie Boards, and endless Christmas fun at Virgin Hotels Chicago. Each ticket includes a 90-minute reservation and a holiday-themed welcome cocktail or mocktail. Additional drinks and holiday-themed bites will be available for purchase on-site.
Where: 203 N. Wabash Ave, 2nd Floor, Chicago, IL
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PRESENTS
Watch Holiday Movies with Boozy Hot Chocolate
JoJo's Winter Wonderland is hosting holiday movie nights on December 14 and 21 this season. Stop by for an unforgettable evening filled with your favorite holiday movies, creative ornament painting, and a bottomless, boozy hot chocolate bar that will keep your spirits merry and bright!
Where: JoJo's River North: 23 W Hubbard St, Chicago, IL
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See A Magic Show at Storyville
When you need a break from the cold, head indoors to Storyville for drinks, bites, and up-close magic. This unique magic show is a blend of vanishing animals, mind-boggling card tricks, and jaw-dropping mind-reading. Perfect for date nights, special occasions, or just a fun night out.
Where: Storyville: 712 N Clark St, Chicago, IL
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Make the Most of the Season at Gallagher Way Winterland
Spend a day at Wrigley Field during Gallagher Way Winterland! You can check out Santa’s workshop, ice skate on the field, shop Christkindlmarket Wrigleyville, and enjoy all of the rides and attractions the special event has to offer. This year is better than ever, so don’t miss out on this unique opportunity.
Where: 3635 N Clark St, Chicago, IL 60613
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Cozy Up at the ChiTown Drive-In
The drive-in theaters of the past are making a comeback! Take your car to the cinema this season to get your fill of holiday favorites like Elf and the Chicago classic, Home Alone. The best part is you can bring all of your favorite snacks and wear your pajamas!
Where: 2343 S. Throop Street, Chicago, IL 60608
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Volunteer Or Donate To The Greater Chicago Food Depository's Food Drive
Volunteering is one of the most rewarding and vital things you can do during the holidays. Help the Chicago Food Bank provide meals to those in need by donating items or volunteering time at one of their various locations.
Where: 4100 W Ann Lurie Pl, Chicago, IL 60632
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Cozy Up with a Hot Cocoa
Nothing is cozier than sipping a toasty hot chocolate on a cold winter day. Make your way to BomboBar for a salted caramel bomboloni and rotating hot chocolate, or head to Mindy's Bakery for their classic bakery blend, served with a house-made marshmallow!
Where: BomboBar: 832 W Randolph | Mindy's: 1623 N. Milwaukee Avenue
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Sip Cocktails at an All-Pink Holiday Bar
Add a little pink to your holiday festivities this year and head to A Pink Wonderland in River North, Chicago's newest festive pop-up featuring pink bows, baubles, tinsel, and drinks! Perfect for a girls' night out, winter birthday, or really anyone who loves pink and the holidays!
Where: 324 W Chicago Avenue, Chicago, IL
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Take an Espresso Martini Workshop
Looking for a cozy winter date night, a fun night out with friends, or a holiday team-building activity with the office crew? This espresso mixology class will do the trick. Located in a sleek and stylish mixology studio, you'll get to shake, stir, and garnish your way to Espresso Martini mastery, plus enjoy light bites along the way.
Where: Storyville Chicago: 712 N Clark St. Chicago IL
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Visit Ben’s Christmas Tree Farm
Chicago has a plethora of tree farms outside the city if you're into making a short day trip to cut down your own tree. Head to Ben's Christmas Tree Farm, where you and your loved ones can choose from eight varieties of pines, then retire to the Warming Barn with a cup of complimentary hot chocolate with your spoils.
Where: 7719 Ryan Road, Harvard, IL 60033 (Ben's flagship farm)
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Shop The Christkindlmarket
Christkindlmarket is back for 2023! This annual Chicago activity should be on everyone’s winter bucket list. The iconic market is coming to two locations in Wrigleyville and Aurora, along with the usual location in Daley Plaza. From holiday treats to shopping to so much more, there’s something here for everyone!
Where:
Daley Plaza: 50 W Washington St, Chicago, IL 60602
Wrigleyville: Gallagher Way, 3635 N Clark St, Chicago, IL 60613
Aurora: RiverEdge Park, 360 N. Broadway, Aurora, IL 60505
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Explore Verse Immersive
Winter is the perfect time to explore Chicago's museums and indoor exhibits. Check out Verse, an immersive augmented experience that puts you at the center of an engaging story. You'll walk around wearing fully transparent headsets while you see and interact with an unbelievable story. Visitors are encouraged to look everywhere and touch everything! It's definitely a one-of-a-kind experience and a welcome escape from the cold!
Where: Verse Chicago: 108 North State Street, Suite 150, Chicago, IL
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Celebrate Chinese New Year
Chinese New Year falls on February 9 this year, but the big celebration in Chicago’s Chinatown will take place on Sunday, February 18. Stop by to enjoy traditional dragon and lion dancing teams, colorful floats, marching bands, and marching groups!
Where: 24th Street and Wentworth Avenue, Chicago, IL
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Watch The Chicago Thanksgiving Parade
Kick off the holiday season with a Chicago tradition—the Thanksgiving Parade! Bring the whole family to see floats, marching bands, giant balloons, and performances by local legends. Get there early to snag a good viewing spot!
Where: State Street, From Ida B. Wells Drive to Randolph
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EXPLORE MORE:
The Top Holiday Markets in Chicago This Season
The Best Unexpected Date Ideas in Chicago
Chicago's Best Hidden Speakeasies
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