The holidays are just a few weeks away, and the first signs of the season are beginning to show around Chicago.
Now is the perfect time to build your own list of fun-filled festivities to enjoy this coming winter, from outdoor ice skating to Christmas markets and beyond.
Luckily for you, Secret Chicago has the planning covered—here are some of the best things to do this winter in the Windy City!
There’s no better winter pastime in Chicago than outdoor ice skating!
This season the Maggie Daley Ice Skating Ribbon and citywide ice rinks will once again open from November through March.
Ice skating in Chicago offers a fun and affordable activity for all ages. Many rinks offer free admission if you bring your own skates, and skate rentals for just a few bucks.
Enjoy some festive cheer at the Christkindlmarket
It wouldn’t be the holiday season in Chicago without a visit to the Christkindlmarket. And the beloved holiday market returns this November!
The Christkindlmarket will once again pop up in its traditional home at Daley Plaza in the Loop, and its second city location at Wrigley Field/Gallagher Way.
Guests can shop unique holiday gifts, enjoy German comfort foods like bratwurst and hot pretzels, and sip spiced Glühwein from signature Christkindlmarket mugs.
Click here for daily hours and more information.
Watch the annual Tree Lighting Ceremony in Millennium Park
The unofficial start of the holiday season arrives on Friday, November 20, with the 113th annual Chicago Christmas Tree Lighting Ceremony in Millennium Park.
Thousands of Chicagoans will come together to watch the city Christmas Tree light up in all its glory.
Attendees will also enjoy live musical performances, a fireworks display, and other entertainment.
Take a hot tub boat cruise along the Chicago River
The Chicago Boat Company is bringing back its popular hot tub boats this winter in Chicago, and if you haven’t tried them yet let this be the year!
Each boat seats up to 6 passengers and reservations start at $300 for a 90-minute ride.
Divided by a party of 6, that’s only $50 a head—not a bad deal!
So grab your friends, some towels, and your drink of choice (no glass bottles!), and you’re all set for a one-of-a-kind experience.
Learn more and book your boat here.
Sip festive cocktails at Frosty’s Christmas Bar
Chicago’s original holiday hang-out is back this season!
Frosty’s Christmas Bar will once again pop up in River North with three bars across two floors, festive cocktails, fun photo ops, holiday music, and endless fun.
Official 2026 pop-up dates are still pending, but you can sign up to join the waitlist today here.
Shop for gifts at a holiday market
Winter in Chicago means holiday markets galore, and we’ve got a few extra-special events for you to keep on your radar.
First is the Chicago Artisan Market, back for four separate dates November through December in Fulton Market and Ravenswood.
Guests can shop hundreds of vendors offering handmade gifts, gourmet food, art and home decor, and much more.
Next is the Salt Shed Holiday Market on December 6, and this year’s market is bigger than ever. Expect 70+ vendors and a massive selection of jewelry, vintage clothing, ceramics, and more.
Celebrate the magic of the holiday season with a visit to the Lincoln Park Zoo for the annual ZooLights festival.
This year’s spellbinding event will feature thousands of lights and themed displays.
Along the way, guests can visit their favorite animal residents, enjoy holiday treats and festive music, roast marshmallows around bonfire pits, and take a ride on the Ferris Wheel (Ferris Wheel tickets cost extra.)
Click here to explore ticket options and learn more.
Enjoy a festive night out at the Jack Frost holiday pop-up
One of Chicago’s largest outdoor holiday pop-ups is back this winter and you won’t want to miss out!
The Jack Frost Christmas pop-up will once again return to Fulton Market with ice skating, gift vendors, axe throwing, cocktails, bumper cars, and more!
Official 2026 dates are pending, but you can click here to join the waitlist today.
Ride the CTA holiday train
It’s almost that time of year again—you step onto the “L” for your typical commute home after a long workday and find yourself engulfed in a winter wonderland!
The annual Chicago Transit Authority (CTA) Holiday Train will roll into stations across Chicago from late November through December.
The train will feature festive light displays, holiday music, pictures with Santa, and other interactive fun.
The Magnificent Mile Lights Festival is back for its 35th edition this winter, bringing a sprawling parade and a full day of fun to the heart of Chicago.
The day’s festivities begin with a street fair from 11 a.m.–4 p.m., followed by the parade at 5:30 p.m., and a fireworks finale.
Attendees can expect hundreds of light displays, festive parade floats, visits from Santa and Disney characters, and more.
