Our Guide to Chicago’s Holiday Events 2022

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Whether you’re naughty or nice, we’ve got you covered for the holidays. See below for events that will make you want to deck the halls this holiday season.

Visit Christkindlmarket

Christkindlmarket’s 2022 Mug

Everyone Chicagoan knows about Christkindlmarket and its longstanding history. Inspired by the 16th-century Christkindlmarket in Germany, Christkindlmarket Chicago is the place to make holiday memories with your loved ones. With locations in Wrigleyville, Daley Plaza, and Aurora, Christkindlemarket is easily accessible and free to visit. All Chicagoans love to collect Christkindlmarket mugs because the design changes every year. While other folks hang up their stockings, we put out our Christkindl mugs. The vendors are the real stars of the show. With a wide variety of German food, tasty drinks, hand-made ornaments, and picture set-ups, you’ll want to try everything! Christkindlmarket gets quite busy, so check out their FAQs page to plan your visit today.

See The Nutcracker with Joffrey Ballet

Known for its graceful dancers and astounding choreography, Joffrey Ballet will take your holiday magic to new heights. Choreographed by Christian Wheeldon, The Nutcracker combines Tchaikovsky’s iconic music with Chicago’s cultural heritage. Young Marie and her Nutcracker prince journey through Chicago’s 1893 World Fair, weaving in and out of reality on Christmas Eve. Complete with magical sights, sounds, and enchantments, all the classic Nutcracker characters will make your holiday season bright. With a variety of performances, Joffrey Ballet will create new holiday memories and bring you the gift of Christmas. Visit their schedule and tickets page to purchase your spot today!

The Art Institute Lions

Everyone loves the rich history The Art Institute brings to Chicago. The Art Institute wouldn’t be complete without its lions, and these beasts are getting decked out for the holidays. Starting on November 25th, The Art Institute Lions will don evergreen wreaths, and the Neopolitan creche will be on display. While you’re there, you and your family can come Home for the Holidays by enjoying breathtaking art, seeing current exhibitions, or making art together. Get your tickets today to get out of the cold and see the iconic lions!

Millenium Park Holiday Sing-Along

It’s finally time to sing Christmas music, and choirs throughout Chicago invite you to join in at Millenium Park’s Holiday Sing-Along. On December 2nd, 9th, and 16th, head to The Bean to hear local choirs perform classic Christmas hits. Admission is completely free, and each performance will start at 6:00 pm. This Holiday Sing-Along is perfect for any Chicagoan or visitor looking to take part in diverse holiday traditions. Whether you’re a good singer or not, these Chicago choirs want you to embrace your inner Christmas spirit and sing along with them! Head here to see the full list of events, performing choirs, and other helpful information.

Peppa’s Cozy Winter Fun

This Christmas, give the gift of oinktastic fun at Peppa Pig World of Play! Grab your favorite Peppa Pig fan and get ready to see Peppa in her winter outfit. Put on your favorite Christmas sweater and head out to Schaumberg for a variety of memory-making activities. Try out their new winter outfit matching game, get a cute family Christmas card photo, and snuggle up for a showing of winter-themed episodes. This event is running from December 2nd through the 31st, so get your tickets while you can. Visit their tickets & passes to learn more about the event and reserve your spot!

Culinary Experiences with Paramount Events

Centered around expertly-curated culinary experiences, Paramount Events is committed to making your holidays merry and bright. Join Paramount Events for their Seasonally: Holiday Edition events, complete with the best holiday trends, hosting hacks, sustainable gifts, and more. Ready to learn the tips and tricks of a Peppermint Martini? Paramount Events has you covered. If you’re a foodie, stay tuned for how to make their Winter Wedge Salad, topped with Herbed Buttermilk Dressing. Read their event inspiration and plan your culinary event here!

The Whistler’s Annual Princemas

Celebrate all things purple with Logan Square’s OG craft cocktail bar, The Whistler. On December 23rd, you can join in on an evening dedicated to the Purple One. Local DJs will be spinning all your favorite tracks alongside unreleased music and rare cuts from The Vault. Complete with live performance clips, music videos, and TV appearances, Princemas will help you “get through this thing called life.” While you’re getting your groove on to these funky tunes, sip on The Whistler’s rotating menu of inventive craft cocktails. Even though cover is free all night, early arrival is highly encouraged!

Ride the CTA Holiday Train and Bus

Chicago holidays are like no other, especially when our transit gets festive! Since 1992, the CTA has run its Holiday Train & Bus to deliver the holiday spirit to anyone commuting throughout Chicago. In addition to transporting passengers, the Holiday Train & Bus delivers food baskets to various charities around the city. Each food basket contains the fixings for a complete meal, and the CTA hopes to donate over 600 baskets this year! As the train and bus pull up to their stops, passengers can enter a winter wonderland, complete with Santa, twinkling lights, seasonal images, and holiday music. Head here to see the schedules for both the train and bus so you don’t miss out on the magic of the season.

Holiday Programming at The Second City

Fill your holidays with laughter at The Second City. Just like snowflakes, no two shows are alike! What the Elf is the perfect toast and roast to round out 2022. Grab some hot cocoa for these hot takes, and look back on 2022 with some cheer. Best of The Second City Holidays presents the best of over 60 years of comedy! Join up-and-coming comedians as they perform their favorite holiday hits. Holiday Improv Brunch combines everyone’s two favorite things: brunch and improv comedy! Come and enjoy mimosas, whether you are on the naughty or nice list.

Given four stars by the Chicago Tribune, Do the Right Thing, No Worries If Not lets you laugh about the things we have in common. Let your guard down and join fellow audience members as you explore your true self! Finally, Great Altercations faces off against the little things that annoy us and make us laugh together. With all these holiday programs, you don’t want to miss out. Tickets start at $29 and can be purchased here!

Museum of Ice Cream‘s annual Pinkmas

From November 17th until January 9th, MOIC’s Annual Pinkmas is back for the holidays! With over 13,000 square feet of deliciousness, MOIC is a museum that explores sweet treats. They’ve added festive crafts, a larger-than-life snow globe, and so much more for the holiday season! Plus, all guests get to sprinkle their way through the Pinkmas tree forest, build a take-home gingerbread house, and sample holiday ice cream flavors. The fun doesn’t stop there. MOIC’s Cafe will serve holiday drinks and food, complete with their Gingerbread Milkshake and Mulled Apple Cider. With your ticket, you receive unlimited access to everything mentioned here. Visit this page to grab your ticket today!

River Roast Thermos Cocktails

Snuggle up this holiday season with River Roast! The wintry riverfront is much more enjoyable with a cozy cocktail in hand. Through December 31st, you can experience their Thermos Cocktails every day of the week, and live music on Thursdays. Made with Kahlua and Chile Liqueur, their Smokey Hot Cocoa will warm your insides and your spirits. Their Spiced Apple Cider is sure to be a hit as well, complete with Spiced Rum. Finally, enjoy their Mulled Wine, made with Red Wine, Brandy, and more. Each of these cocktails is $22, so you can try them all!

Holidays on the Water with City Cruises

City Cruises Chicago invites everyone to join in on their holiday cruises. Perfect for all ages, these cruises will keep you cozy while giving you unparalleled views of Chicago’s skyline. These cruises for Thanksgiving, Christmas, and New Year include food, drinks, and holiday cheer. We love their Christmas Eve Premier Dinner Cruise, complete with a DJ set, a 3-course holiday meal, festive cocktails, and holiday fun for the whole family. This is just one of their amazing holiday packages. Head here for more information on each cruise. Book your ticket today for unforgettable memories.

American Blues Theater and “It’s a Wonderful Life”

Photo by Matthew Brosilow

The American Blues Theater celebrates diverse and multi-generational artists, all while exploring the American identity through performance. From November 23rd until December 23rd, celebrate the holiday season with American Blues Theater and their production of “It’s a Wonderful Life.” Filled with original music and classic holiday carols, “It’s a Wonderful Life” explores the story of George Bailey, a poor man in need of a Christmas miracle. Artistic Director Gwendolyn Whiteside is grateful for our growing audiences and hopes to create a new tradition for many Chicagoans.” You won’t want to miss out on this long-standing Christmas tradition. Head here to purchase your tickets today. 

State Street Holiday Market

From the award-winning Sundays on State series, Chicago Loop Alliance is making the holidays merry with its Christmas addition. Starting on November 18th, join the Chicago Loop Alliance for their State Street Holiday Market. While Sundays on State celebrated the summer, State Street Holiday Market will take the party indoors, complete with artisanal materials and festive gift options. This is a great way to support local businesses and enjoy all of the Holidays in the Loop programming! Open on Friday, Saturday, and Sunday from 11 AM until 6 PM, State Street Holiday Market changes the events every week. From special deals to riding the Holiday CTA Train, you won’t want to miss out!

Wrigley Wonderland

The sleigh bells are ringing and the drinks are pouring at Wrigleyville Wonderland! Usually centered on baseball, Wrigleyville has turned its neighborhood sports bars into the North Pole. Deuce’s MLB Bar, Underground Lounge, Roadhouse 66, and more decorated every inch of their spaces to help every grinch get in the holiday spirit. With new names such as 8 Crazy Nights, Jingle Junkie, and Santa Baby, these bars know how to throw a holiday party. You have until January 8th to visit these bars, so make weekend plans with your elves to visit at least one of these bars!

Head here for more holiday pop-up bars!

Winterland at Gallagher Way

We thought the Cubs and Wrigleyville atmosphere couldn’t be topped. Well, this holiday season, Gallagher Way has made us love Wrigley even more! Complete with family fun and interactive experiences, Winterland at Gallagher Way has events for everyone, enough to fill up a whole day. Admission to Christkindlmarket and Santa’s Workshop is free for everyone, and no advance tickets are required. To enter Wrigley Field and the holiday magic that awaits you inside, tickets are required in advance. Tickets can be used at any of the attractions inside Wrigley Field, including Chimney Toss, Hot Cocoa Cups, and Ice Skating. Plus, their ice skating rink even does bumper cars. Whether you come for one activity or get tickets for the whole day, Winterland at Gallagher Way is sure to make your spirits bright.

Glessner House‘s Christmas Candlelight Tours

Built in 1887 as a radical departure from traditional Victorian architecture, Glessner House preserves a piece of the Nineteenth Century, right here in Chicago. This holiday season, you can celebrate authentic, old-fashioned Christmas traditions with a candlelight tour. Led by a docent, this Christmas tour will take you through Christmas extrvaganza of the Nineteenth Century, including a 10-foot tree, period ornaments, and holiday crafts. After the tour, enjoy hot cider and holiday cookies. Visit their events page today because tickets are selling out fast!

Shopping Extravaganza + Holiday Treat Stroll

Saturday, December 3rd is Lakeview East’s Shopping Extravaganza and Holiday Treat Stroll. Supporting local merchants has never been easier. For one day only, local businesses will offer 25% off local gift cards! Plus, while you visit these businesses, they will be giving out treats for everyone stopping in. This event runs from 11 AM to 3 PM, so be sure to get your gift card before the day is over!

Lakeview East Holiday Tree Lighting

Lakeview East’s Chamber of Commerce presents its 2022 Tree Lighting Ceremony. While it’s no downtown tree extravaganza, their Christmas Tree is still going to fill up your holiday spirit. Stop by the corner of Waveland and Broadway on November 22nd for the ceremony. From 5:30 PM to 6:30 PM, the whole family can experience the joy of Christmas. There will be hot cocoa, carolers, candy canes, and visits from Frozen’s Anna, Elsa, and Olaf. Plus, Santa will even stop by before heading to the North Pole to work on Christmas gifts. The tree lighting will make you feel connected to your community and excited for the festivities to continue!

Giver’s Gift

Back for its 26th year, Lakeview East’s Giver’s Gift promotions are all about shopping local for the holidays. With more businesses than ever before, this partially-virtual event will motivate you to finish your holiday shopping. First, collect $300 in receipts from local Lakeview East businesses. Next, fill out this form to enter your receipt. Once you hit the minimum amount requirement, you will receive a $50 gift card to spend at any Lakeview East business. Once you receive that gift card, look at the list of businesses that accept it! Complete with supporting local businesses and finding fun gifts for the holidays, Giver’s Gift will get your Christmas shopping done with an amazing reward after. For questions or concerns, head to the webpage, email info@lakevieweast.com, or call (773) 348-8608.

Greektown’s Holiday Shopper’s Rewards Program

With the holidays approaching fast, Greektown will help you save money and support small businesses. From November 1st through December 31st, spend at least $250 at local Greektown businesses, and receive a $50 Visa gift card. After visiting a local business, be sure to save your receipt, and mail it in once you’ve reached the total amount. The Holiday Shopper’s Rewards Program gives you a great opportunity to pick gifts early, make a difference at local businesses, a splurge a little bit on yourself! Don’t wait! Visit the link above to get started today.

Illumination: Tree Lights at Morton Arboretum

Light up Chicago’s winter with Morton Arboretum’s 10th year of Illumination: Tree Lights. As the brightest and boldest light show ever, Illumination will display over 50 acres of dazzling holiday displays. This year, Illumination will feature six never-before-seen spectacles of light and color. For the finale, head to their new Grand Garden for an array of shapes from the ground into the air, complete with a laser light show set to music. Featuring local craft brews and a late-night party, IllumiBrew and Electric Illumination are perfect events for adults. For the family, enjoy their Treemagination or lit-up Human+Nature exhibit. You have until January 7th to enjoy this event, but it’s a perfect way to get in the holiday spirit early!

League of Chicago Theaters

With a collection of over 250 theaters across all of Chicago, League of Chicago Theaters has a production for all your holiday wishes. Many theaters are performing A Christmas Carol and Elf the Musical. You can even search their theaters by Chicago neighborhoods! No matter what performance you choose, you’ll make new memories and see creative takes on all the classics. Head to their holiday tickets page for a larger list of shows and openings to purchase your tickets.

Lookingglass Theatre Company’s The Steadfast Tin Soldier

Photo by Liz Lauren

From November 13th until January 8th, Join Lookingglass Theater for their production of The Steadfast Tin Soldier. Based on Hans Christian Anderson’s story of a little tin soldier that does not give up, this play is a family-friendly spectacle of light and movement. Head to their events page to purchase your tickets today. After you go, you’ll know why the Chicago Tribune says this about the play: “★★★★ A treat for all ages! It’s transformational, truly. Barely more than an hour long, this is a holiday experience you don’t want to miss.”

The Immersive Nutcracker

For nearly 130 years, The Nutcracker has delighted families and children of all ages. Let the popular Christmas classic The Nutcracker come to life with an immersive, majestic experience. Opening at Lighthouse ArtSpace Chicago, classic characters will come to life in this modern rendition. Transporting you into a world of winter magic, Sugar Plum Fairies and the Mouse King will be right at your fingertips. Classical music will sweep you off your feet and into holiday wonder. This event will take place until January 2nd, but tickets are selling out fast! Head here to find the best time to celebrate this unforgettable Christmas story.

Bricktacular Holidays with Legoland Discovery Center

Build your very own Lego Snowman!

Forget making snowmen out of snow, and head to the Legoland Discovery Center for their Holiday Bricktacular event. Head out to Schaumberg to build a Winter Wonderland out of Legos. You’ll have the chance to hunt for holiday presents, complete with your chance to win a one-of-a-kind holiday prize! Plus, you can take some great family photos with their Giant LEGO® DUPLO Sleigh and meet Santa. The LEGOLAND® Discovery Center Chicago Retail Store has a gift for everyone on your list, and you’ll get out of the cold while checking all the boxes. If you go on the weekends, be sure to meet the LEGO® Gingerbread Man for a sweet treat. Visit their event page to grab your tickets today.

Written by Maddie Belland

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