EPIC List of Holiday Events and Winter Activities in Chicago

November 8, 2022

It’s that time! The holiday season is HERE and I feel like it’s starting earlier and earlier every year? Maybe because so many of the Chicago holiday events sell out so quickly! Either way, I wanted to get this list out to you sooner rather than later, so here is a HUGE list of indoor and outdoor holiday events and activities happing in Chicago this year! They are divided into lots of categories so hopefully you find it helpful! We’ll continue to update as more events get announced. And stay tuned for our Holiday Pop-Up Bar & Festive Restaurants Guide!

Afternoon Holiday Tea
Langham has a beautiful lobby for the holidays and have tea time.

Langham Hotel


Tea time at The Gwen

Tea time at Hotel Zachary


Holiday decorated lobby at Four Seasons

Holiday decorated lobby at Four Seasons

  • The Drake Hotel – For the classic old-school Chicago experience: The Holiday Afternoon Tea reservations are available in both Palm Court and on selected dates in Club International. A live harpist and holiday carolers will be stationed to perform on select dates through Christmas. Adult tickets start at $74.
  • Four Seasons Hotel Chicago – For the luxury experience: Served in the Social Lounge, a vibrant art and gathering haven, the winter wonderland-inspired tea features savory bites and sweet treats while benefiting our community. Adult tickets start at $125. The lobby is beautiful during the holidays!
  • The Gwen Hotel – For the most fun experience: Tipsy Tea at Kostali is a favorite of mine for ladies brunch! Adult tickets start at $65. This would make a great holiday outing with friends!
  • The Langham Chicago – For The Crown experience: Pavilion is home to The Langham Afternoon Tea, the signature afternoon tea that first debuted at The Langham, London in 1865. Tickets for adults start at $125.
  • LondonHouse Chicago – For the modern tea experience: LondonHouse afternoon tea service takes a non-traditional approach to high tea. Offered daily in the Bridges Lobby Bar, located on the second floor of the hotel with stunning views of the Chicago River and famous bridges. Holiday Tea service is $85 for adults and $45 for kids (ages 10 and under).
  • Vanille Chicago – For the French experience: Vanille Patisserie offers Holiday Tea in Lincoln Park. Best for parties with 4-10 people. $79 for adults.
  • The Beatrix Potter Holiday Tea Party – presented by the Chicago Children’s Theatre and best for ages 2-6. From their website: Four adorable Beatrix Potter favorites come to life in this mesmerizing, interactive trunk and puppet show, complete with original music. Levers are pulled and cranks are turned to reveal images that surprise and delight. Our charming storytellers interweave the classic narration and guide gentle interactive moments, recruiting young watchers to join the adventure. After the show, come up on stage to gently play with the puppets and take pictures. Then, head to the lobby for a festive spread of chocolate milk and cookies!


Curling and Bumper Cars

Curling for winter activities

Curling at the Emily Hotel


Curling for winter activities

Yurts at the Emily Hotel rooftop curling


Heated patio fire pits at The Emily Hotel



Holiday Markets



Vintage market to holiday shop

Vintage market at Salt Shed and I found this glasses from the 80’s!


  • Christkindlmarket: They have a new Aurora location, but my favorite is at Gallagher Way because it’s a bit smaller and now they are offering ice skating INSIDE Wrigley Stadium. You can shop the market and then ice skate! This is one of my favorite holiday events of the season!
  • Markets for Makers Holiday Market: Featuring over 80 makers who mostly call Illinois or the Midwest home, this Ravenswood event will feel like Etsy IRL! November 19-20, tickets start at $8.
  • One of a Kind Holiday Show: Running December 1-4 at the Chicago Mart, this market hosts 500 artists, designers, and makers. Tickets are $15 and are valid for entry all four days of the show. Children under 12 are free. A portion of all ticket sales will benefit the Ann & Robert H. Lurie Children’s Hospital of Chicago.
  • Randolph Street Holiday Market: This market has a ton of stuff! It runs December 17-18 in the Plumbers Hall Building in the West Loop. $15 at the door and $10 in advance!
  • Winterglow at Salt Shed: I’m super excited for this new venue in the former Morton Salt building! We went to a market in the summer and it was SO FUN! Winterglow runs for two weekends, Dec. 2-11, with an artisan gift and home goods market, a beer garden, s’mores kits, and more! Tickets are $6.
  • Millennium Park Art Market – This market is meant to coincide with the official tree lighting ceremony the weekend of 11/18 – 11/20. The Art Market, in the Chase Promenade North tent, will feature local artists selling a variety of items including jewelry, pottery, drawings, paintings and more. Admission is free.
  • State Street Holiday Market – State Street comes indoors for a magical shopping experience with local artisans and Sundays on State small businesses. This event runs November 18–December 18 and is free!


Holiday Tree Sightseeing

900 Shops decor and tree


Wrigley Building


Holiday photos in front of the Wrigley building

Some of my favorite photos in front of the Wrigley Building


Union Station’s tree last year was so pretty!


Millenium Park tree


Walnut Room at Walnut Room


Waldorf Astoria


  • Macy’s State Street Walnut Room Tree: Reservations for the Walnut Room went so fast this year! But you can always stop by the store and check it out. Or if you are looking, there might be some last minute cancellations! The Walnut Room always has the best tree and has been a Chicago holiday events classic for years!
  • Millennium Park: Watch the Christmas Tree Lights go on in Millenium Park. The annual tree lighting is on November 18th this year! They also have Millennium Park Holiday Sing-Alongs happening every Friday from 6-7pm in front of the tree. This could be fun for out-of-towners! There is also a brand new restaurant/bar that just opened at the park. Maybe you can grab a reservation and dine there to see the tree being lit! Their website has more information.
  • Waldorf Astoria tree: This courtyard tree is huge and gorgeous!
  • 900 Shops on Michigan Avenue has a beautiful tree and it’s decorated nicely for the holidays!
  • Wrigley Building Tree: Another courtyard tree in a magical location under the Wrigley Building bridge. We took our family photos here last year! The lights go on November 18, 2022.
  • Union Station also has a beautiful tree! Snap some photos in front of it!


Ice Skating

Ice skating at Gallagher Way


Ice skating at Millenium Park

  • Gallagher Way Ice Skating: Yes, you can ice skate in Wrigley Field this year!! Tickets are $20 for skate rental or $12 for rink access only.
  • Maggie Daley Park or McCormick Tribune Ice Rink: Both of these have free admission, but you need to reserve tickets online for your session and rent skates when you get there for $16-20. Both rinks’ reservation dates are released 2 weeks in advance of the session date but they don’t fill up that quickly ahead of time. The rinks opens 11/18, It’s really pretty when there is fresh snow fall! Check out their website to make reservations!
  • The Peninsula Chicago: You don’t have to be a guest of the hotel to skate on their rooftop rink! The Sky Rink opens November 25 Skates are available to rent for $20 for adults and $10 for children 12 and under, with 100% of the skate rental proceeds donated to two Chicago children’s charities: Ann & Robert H. Lurie Children’s Hospital of Chicago, and Hephzibah Children’s Association.
  • Midway Plaisance: This South Side Ice Rink opens November 25, 2022. Pre-registration is required and registration begins on November 18. Open skate times have free rink access with a $7 skate rental fee.
  • Parkway Bank Park in Rosemont: The Chicago Wolves ice rink opens November 19 along with their Light Up the Park tree lighting ceremony. Admission to the rink is free and skate rentals are $8.
  • See Brookfield Zoo, Light Up the Lake, and Jack Frost below for more ice-skating opportunities!


Immersive Light Shows

Light up the Lake is back at Navy Pier and they have indoor ice skating!

Let it Shine Light Show

  • Amaze Light Festival: The Amaze festival has moved to Tinley Park this year. We went last year and the kids LOVED it! They have a holiday market, nightly stage shows, a million lights, candy shop, tubing, a train ride, and a toy shop! Adult admission is $36.
  • Holiday Magic at Brookfield Zoo: Over 2 million lights, a skating rink, illuminated animal sculptures, a 600-foot tunnel of lights, tons of photo ops, and more! Free for members of the zoo, adult tickets are $24.95.
  • Illumination: Tree Lights at The Morton Arboretum: Explore 50 acres of the Arboretum’s majestic trees during this one-of-a-kind spectacle of color, light, and sound! Tickets are between $11-$22 for members and $16-$27 for guests, depending on the date.
  • Let it Shine Light Show: This drive-thru light display synchronizes with a radio station. Locations this year are in Northbrook and Schaumburg. Tickets are per vehicle and are $32.99-$42.99 depending on the day of the week. This is best for family members who would find a large park to walk through difficult or smaller kids that you just want to keep strapped in while they experience the magic. 😉
  • Light Up the Lake: Located at Navy Pier, its one of MY FAVORITES! One of the best holiday events for families I think! They haven’t really done a big event since Covid, so I am hoping everything is back this year. It has SO much. Games, Santa visits, carnival rides, ice skating, and more. It’s SO much fun! Great for families with kids of all ages. Find more info here.
  • Lightscape at the Chicago Botanic Garden: The Botanic Garden light show in Glencoe always delights. Walk through a guided 1.25 mile trail throughout the park while lights dance off the trees to synchronized music. Take a break halfway through for beverages and s’mores kits and watch the light show over the pond by an open fire. Tickets go quickly but it seems as though they have added capacity since last year! $30 for adult members, and $32 for non-member adults.
  • Sparkle Light Festival at Impact Field in Rosemont: Walk through villages with millions of lights, slide down two stories of ice, take the Holly Trolly, and more! Tickets are $25 for adult admission and train rides, and the slide is an additional $22 per person for unlimited rides.
  • ZooLights at Lincoln Park Zoo: This is the quintessential Chicago holiday light experience! ZooLights is either free or $5 depending on what night you go. Plus they have several fun events like Adults Night Out: Holidaze! and The Chris White Trio Tribute to “A Charlie Brown Christmas.”


Indoor Activities

Color Factory is Chicago will be decorated for the holidays!

Color Factory


  • Christmas Around the World and Holidays of Light at MSI: This exhibit has been happening for years at the MSI and it’s so nice! Plus new holiday LEGO in the Art of the Brick, 12 Days of Bricks. This was the kids absolute favorite exhibit I think all year. This would make the best experience gift too!
  • Color Factory Winter Colorland: The new Color Factory immersive art experience in the Willis Tower is fantastic! I took my 6-year-old son when they opened and he has been begging to go back. Beginning November 17, they will have a Winter Colorland theme and we’re taking my almost-4-year-old for her birthday! I highly recommend it! Use code GOODLIFE for 20% off tickets!
  • Museum of Ice Cream Pinkmas – The Museum of Ice Cream transforms into a pink winter wonderland, called Pinkmas, this season. They’ll have limited-time installations and ice-clusive Speakeasy menu items as well as holiday activities like making gingerbread houses and decorating Pinkmas trees!
  • The Immersive Nutcracker: A Winter Miracle: Another new immersive exhibit for the kids this holiday is the Nutcracker Immersive, by the same company who produced the Immersive Van Gogh. It’s at the Lighthouse Artspace which is a gorgeous event space – I love their cafe lounge. The kids will be able to dance and explore the space while the iconic Nutcracker music plays and scenes from the ballet are projected from ceiling to floor. The exhibit opens November 19 and tickets can be bought individually or in a discounted family pack. Buy your tickets here before they sell out!


Outdoor Activities

  • CTA Holiday Train: More details are coming soon but seeing Santa on the festive holiday CTA train is always a treat! They’re offering more chances to catch sight of him this year so I’ll be checking the schedule in December. One of Noah’s favorite holiday events for sure!
  • Hyde Park Holly-Day: On December 3, the University of Chicago presents a day of free, fun activities for the whole family like ice carving demonstrations, holiday crafts, an ice sculpture stroll, photos with Santa, live reindeer, Buddy the Elf, and more!
  • Jack Frost Winterfest Pop-Up: 10,000+ lights, winter tubing, ice-skating, bumper cars, axe-throwing, fortune tellers (?!), a full bar, and a Christmas tree farm. What more could you want in a winter fest? Tickets start at $15 for adults which includes admission and skating rink access. They have tons of packages depending on what activities you want to do!
  • Southport Holiday Stroll and Cocktail Crawl – Friday, December 2. Tickets go quickly for the cocktail crawl but at the time of writing, they are still available! The Holiday Stroll is free and includes special discounts from local businesses, carolers, photos with Santa, holiday treats, and other surprises!
  • Winterland at Gallagher Way: My family and I love visiting Gallagher Way during the holidays! They have a Christkindlmarket that’s free to attend and then in Wrigley Field, there’ll be a carousel, rides and games, ice skating, and ice bumper cars! I’ll be visiting this year very soon, so keep an eye on my IG for a sneak peek! Entrance to Wrigley Field is $5 and attractions will cost additional.


Theatre and Performances

Northlight Theater Christmas at Pemberley

  • Baby Shark Live! Christmas Show: Just want it sounds like! There’s a matinee and evening show on December 23 at the Rosemont Theatre.
  • A Christmas Carol: The classic Christmas show presented by the Goodman Theatre is the gold standard.
  • A Christmas Story, the Musical: From the songwriting team behind Dear Evan Hansen, La La Land, and The Greatest Showman, A Christmas Story, The Musical, brings the beloved 1983 movie to musical life on stage!
  • Cirque Dreams Holidaze: This fantastical and family friendly show from the creators of Cirque du Soleil celebrates the holidays! December 22 – 24, 2022 at the Auditorium Theatre.
  • Elf the Musical: Another fun holiday movie gets transformed on the stage at Drury Lane Theatre in Oakbrook Terrace.
  • Georgiana & Kitty: Christmas at Pemberley: Northlight Theatre presents the final installment of the Pemberley at Christmas trilogy. The first two were so charming and perfect for Jane Austen lovers!
  • Hershel and the Hanukkah Goblins: Presented by Strawdog Theatre Company at The Edge Off-Broadway. The Chicago Reader said it’s a “…must-see family show for everyone who loves Hanukkah delights with outlandish and amazing puppetry, solid Jewish humor, a play-within-a-play on a stage-within-a-stage, and entertaining audience participation.”
  • “It’s a Wonderful Life: Live in Chicago!”: For over 20 years, American Blues has treated audiences to a live retelling of the Frank Capra classic in a 1940s radio broadcast tradition, making It’s a Wonderful Life: Live in Chicago! the second longest-running holiday play in Chicago! Nov 23 – Dec 23, 2022 at the Chopin Theatre in Wicker Park.
  • The Jinkx and DeLa Holiday Show: Fans of RuPaul’s Drag Race know that Jinkx Monsoon and BenDeLaCreme are the ultimate entertainers. This show is fabulous, smart, and hilarious! December 7 at a the Auditorium Theatre.
  • The Nutcracker: There are quite a few Nutcracker ballets performed throughout Chicagoland, but two stand-outs are by the Joffrey Ballet and Ballet Chicago. The Joffrey performs December 3–27, 2022 at the beautiful Lyric Opera House. Ballet Chicago will perform at the Athenaeum on Lakeview December 9-18. Currently, there is a deal from Groupon for the Joffrey performance.
  • The Steadfast Tin Soldier: Lookingglass Theatre’s annual holiday show. “Based on Hans Christian Andersen’s story about a little tin soldier who never gives up, Ensemble Member Mary Zimmerman’s production is a gorgeous spectacle of music and movement and “an absolute gift… brings us hope, gratitude, and magic (Chicago Reader).”

So that’s it!!! So many Chicago holiday events and I want to do them all..haha im kidding, but it’s the best time of the year! Santa visits and holiday themed restaurants are coming soon! If you need more Chicago holiday ideas or hotels to visit, check here. And happy holidays!!


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