Chicago Holiday Tours, Pop-Ups, Performances, Happenings & More

Holiday Tours To Celebrate the Season 

Bobby’s Bike Hike Chicago Holiday Tour, a festive food and walking tour of Downtown Chicago begins at the end of November and runs through Christmas Eve.

Visitors will see the lights of the Magnificent Mile, the ice-skating rink and Christmas tree in Millennium Park, enjoy a warm and filling deep dish pizza, experience the German-inspired festivities of Christkindlmarket, and toast to a joyful season over a seasonal beverage! This 3 hour Chicago holiday tour is perfect for families, friends, holiday parties, and anyone looking to celebrate the season in an exciting new way. All food & non-alcoholic beverage samples included in ticket price. Pricing begins at $75 per adult/$65 per youth (age 4-11) on Fridays/Sundays and $70 adult/$60 youth on Mondays/Thursdays. All children 3 and under ate $10/$9 when sharing with an adult. 

Special Events Spreading Holiday Cheer

Glessner House, a National Historic Landmark in Chicago, is a cultural center and museum showcasing revolutionary design and celebrating the cultural arts from the late 1800s to the present day. Filled with original artifacts and unique family history, Glessner House prepares to celebrate the holidays with the following special programming: 

  • Children’s Gingerbread House Decorating Party (December 2, 2023) – At Glessner House’s seventh annual Gingerbread House Decorating Party children are invited to create their own mini-gingerbread house to take home.  All supplies are included.  Glessner House will have lots of helpers, so no previous decorating experience is necessary but all children (recommended for ages 3-13) must be accompanied by an adult. Ticket pricing is $25 per pair (one child with accompanying adult) and there are two seatings, from 10:00 – 11:30 a.m. and from 1:00 – 2:30 p.m.
  • We Wish You a Mattie Christmas!  (December 3, 2023) – The tree is decorated and the stockings are hung, so Frances Glessner is planning a very special Christmas luncheon with the assistance of her favorite cook, Mattie Williamson, and you are invited! Join the Glessner team in the dining room for a delicious four-course feast based on the menu for a supper served by the Glessners on Christmas night, 1898. Menu items include sausage and cheeses, chicken timbale, turkey sandwiches with cranberry relish, pickles, olives, and celery, plum pudding, eggnog ice cream, mulled wine and more. During the meal, Mattie will share recipes, ideas on menu planning, preparing the perfect guest list, how she acquired the ingredients, and how parties in the Glessner home were different from those in the surrounding Prairie Avenue mansions. The butler, Frederick, will provide information on the 1898 supper, including the guests who attended, and the musicale that served as the centerpiece of the evening’s entertainment. Ticket pricing is $60 per person, with seatings at 11:30 a.m. and 2:30 p.m., with each seating limited to 26 guests.
  • Christmas Candlelight Tours (December 9-10, 16-17, 2023) – These special one hour docent-led tours will highlight Christmas customs as observed by the Glessner family. The house will feature elaborate decorations of the late 19th-century including a 10-foot tree decorated with period ornaments, toys and holiday crafts, Christmas music performed on the Glessners’ Steinway piano, and the dining table set for an eight-course Christmas feast. After the tour, enjoy complimentary hot cider and cookies. Ticket pricing is $20 per person; each hour-long time slot is limited to eight (8) attendees.

Classic Performances 

A Christmas Carol, the classic holiday tradition that has been running for over four decades in Chicago, returns to the Goodman Theatre with Jessica Thebus directing and Larry Yando reprising his role as the miserly Scrooge. Tickets start at $30 and performances run through December 31, 2023. 

DR. SEUSS’ HOW THE GRINCH STOLE CHRISTMAS! THE MUSICAL is the record-setting Broadway holiday sensation which features the hit songs “You’re A Mean One Mr. Grinch” and “Welcome Christmas” from the original animated special. Max the Dog narrates as the mean and scheming Grinch, whose heart is “two sizes too small,” decides to steal Christmas away from the Holiday loving Whos. Magnificent sets and costumes inspired by Dr. Seuss’ original illustrations help transport audiences to the whimsical world of Whoville and help remind us of the true meaning of the holiday season. Recommended for ages 5+ , performances run 85 minutes with no intermission at the Cadillac Palace Theatre from December 19-31, 2023. Ticket prices begin at $32. 

The Joffrey Ballet’s The Nutcracker by two-time Tony Award®-winning choreographer Christopher Wheeldon, returns to the Lyric Opera House from December 2 – 27, 2023. This version is set during Chicago’s World Fair in 1893, where the young immigrant Marie and her mother, a sculptress creating the Fair’s iconic Statue of the Republic, host a festive Christmas Eve celebration. After a surprise visit from the creator of the Fair, the mysterious Great Impresario, Marie embarks on a whirlwind adventure with the Nutcracker Prince through a dreamlike World’s Fair that highlights the rich cultural heritage of Chicago and the wonder of the season. A ballet in two acts set to Tchaikovsky’s classic score, The Nutcracker features an award-winning creative team, including Tony Award®-nominated set and costume designer Julian Crouch, Caldecott Medal Award-winning author Brian Selznick, Obie and Drama Desk award-winning puppeteer Basil Twist, Tony Award®-winning lighting designer Natasha Katz and Tony Award®-winning projection designer Ben Pearcy/59 Productions. The production was adapted in 2021 by Wheeldon to fit the larger Lyric Opera stage and features live music performed by the Lyric Opera Orchestra, conducted by Scott Speck, Music Director of The Joffrey Ballet. Tickets start at $40.

Holiday Pop-Ups: 

A full-blown tribute to the beloved Christmas movie “Elf”, Elf’d Up is back by popular demand for the 6th year. Elf’d Up is decorated from floor to ceiling with over 1,000 elves of all shapes and sizes, a 10-foot Christmas tree, an upside-down Christmas tree, wreath chandeliers, strands of festive colored lights, specific tributes to the movie-like figurines, wall quotes, snowflakes, Schylling Jester Jack in the Boxes, cut-outs of Buddy the Elf and Miles Finch and more. Each table comes equipped with condiment carriers filled with the “four main food groups”– candy, candy canes, candy corn, and syrup.

Though there are some non-alcoholic drinks on the menu, it’s heavily skewed in favor of Christmas-themed cocktails, so more of an adult atmosphere – for adults who love Buddy the Elf, of course! They have food too, including specialty holiday menu items like Buddy’s Breakfast Pasta which includes spaghetti, topped with maple syrup, chocolate fudge, and mini marshmallows.

Jack Frost Christmas Holiday Pop-Up is turning up the holiday cheer again this year, this time in the heart of Fulton Market! From November 25, 2023 – January 5, 2024, enjoy two acres of winter wonderland with daytime activities like bumper cars and ice-skating, perfect for families. In the evening, adults can indulge in the festive atmosphere by sipping on boozy hot cocoa as you walk through the Christmas tree forest, try your hand at axe-throwing and explore the Christmas market. Challenge your friends to ice curling and snap some epic Christmas pics at the famous holiday photo-ops.Tickets start at $15; hours typically run from 2.00 p.m. – 10:00 p.m. on weekends and 4:00 p.m. – 10:00 p.m. on weekdays but times may vary for holidays and booked events.

8 Crazy Nights, the original Hanukkah bar in Chicago, is back by popular demand for the  fifth year in a row. Where pop-up Hanukkah bars are concerned, The Graystone Tavern is renowned for having the “one and only” in the region. What began in 2019 in Wrigleyville has quickly become a TRADITION!

In addition to all the customary blue and white lights and decorations throughout the indoor area, Graystone has also weather-proofed its beer garden for those who wish to take their celebration outdoors. And, for die-hard original Hanukkah bar Chicago fans, there is a special food menu to please everyone’s palate.

It includes a Brisket Platter, Challah Bread, Matzo Ball Soup, and Latkes, not to mention the vodka-infused, homemade Boozy Jelly Donuts! What’s more, Graystone Tavern’s bartenders offer some pretty remarkable, Hanukkah-themed cocktails like Mazel Tov, Dreidel Bomba, and Hanukkah Harry’s Hot Chocolate. Finally, besides the amazing scrumptious food and Hanukkah-themed drinks, they have spaces set aside for board games like Mitzvah Match, Schmear Build-A-Bagel card game, and Jewish Guess Who? to name a few. 

Celebrate the Holidays in Chicago: Great Happenings

Running now through January 7, 2024, Lightscape at the Chicago Botanic Garden (located in Glencoe, Chicago’s North Shore) returns for its fifth season with an illuminated outdoor trail dazzling with brand new installations from around the world and beloved returning favorites such as the Winter Cathedral and a reimagined version of the Fire Garden.New works from international artists include Lilies, from UK artist Jigantics (illuminated 5-foot lilies float elegantly on water, providing a mesmerizing view from the bridge above and igniting a sense of warmth and excitement), Night Lights, from French artist TILT (delicate lamp-shaped lights that extend nearly 19 feet high amplify a cozy atmosphere with a display of soft ambient colors) and Sea of Light, from UK artist Ithaca (thousands of individually controlled balls of LED light make Evening Island sparkle and dance their way to a bespoke soundtrack in multiple patterns and colors). Tickets sell out quickly so it is recommended to book your time and date in advance; advance tickets for adults (non-members) begin at $34 and children (ages 3-12) at $19. 

The Christkindlmarket celebrates its 27th season at Daley Plaza, its fifth year at Gallagher Way in Wrigleyville, and its second time at RiverEdge Park in Aurora.  This year, Christkindlmarket is introducing its first ceramic beer stein with a holiday-themed design ($20), as well as location-specific $8 souvenir mugs with unique designs at each market (for example: the Chicago mug shows off downtown landmarks like the City Hall building and Daley Plaza’s Picasso sculpture while the Wrigleyville mug shows off Hotel Zachary, the intersection sign of Clark & Addison, and much more.) These mugs are hotly anticipated collector’s items for locals who have turned Christkindlmarket into a holiday tradition since 1996. Modeled after the 16th-century holiday markets in Germany, the free-admission outdoor bazaar is a hub for traditional German fare, delightful warm beverages and handcrafted gifts for purchase, and charming holiday vibes the entire family can enjoy. And now in its third year, another popular favorite is back – the annual Christkindlmarkt ornament, hand-painted and glass blown in Europe, portraying a market scene with holiday elements on its ice blue background ($41 at all info booths).

  • Admission to the market is free but food, beverages, and handcrafted gifts all must be purchased. All markets open on November 17; Aurora and Chicago locations close on December 24 and Wrigleyville on December 31. 

Christmas Around the World and Holidays of Light at the Museum of Science and Industry (running through January 7, 2024) is a beloved annual tradition that began in 1942 with a single tree. Today the Museum features a four-story floor-to-dome Grand Tree, surrounded by more than 50 trees and displays decorated by volunteers to represent holiday traditions from cultures around the world.

This year the museum will also be celebrating the wonders of snow, with an exhibition in the Lower Court featuring intricate photographs of snowflakes taken by Caltech physicist Ken Libbrecht.

Illumination: Tree Lights at The Morton Arboretum (Though January 6, 2024) invites visitors to celebrate the holidays and marvel at how light transforms a magnificent landscape. Journey along a 1-mile paved walking path (that is fully ADA compliant for guests with limited mobility), amid festive music and lighting effects, explore exciting new features and immersive installations. Afterwards, warm up by a cracking fire and roast marshmallows for s’mores, or stop in one of the concession tents for a snack and beverage. Ginkgo Restaurant in the Visitor Center will serve dinner guests view the display’s finale on Meadow Lake. The Arboretum Store will also be open for holiday shopping; gifts include a special temperature-activated, color-changing ceramic mug that will be available for purchase during all Illumination dates. Tickets start at $28 per person for nonmembers. 

People ice skating at the McCormick Tribune Plaza Ice Rink in Chicago’s Millennium Park; December 2021.

The McCormick Tribune Ice Rink in Millennium Park offers ice skating all winter, through March, weather permitting.  Admission is free, but online reservations are required and skate rentals are available. You’ll be surrounded by the downtown skyline, with magical Christmas lights from the City of Chicago Christmas tree reflected in ‘The Bean’ / Cloud Gate sculpture. OR, head over to Maggie Daley Park, right next to Millennium Park, to the picturesque Skating Ribbon that meanders around snow-dusted pine trees and whimsical play spaces. The path is twice the length of a lap around a traditional skating rink. 

The Immersive Nutcracker: A Winter Miracle (November 24 – December 31, 2023) at Lighthouse Artspace Chicago brings cutting-edge technology to meet the artistry of ballet dancers. This mesmerizing 30-minute immersive experience, set to Tchailkovsky’s music, weaves the classic tale of Marie and her toy nutcracker. Join them, on their magical adventure through the Land of Sweets, brought to life by renowned ballet dancers and innovative projection mapping technology. Pricing begins at $29.99 per person. 

  • While you’re here… Lighthouse ArtSpace Chicago is bringing a new pop-up bar experience, Bar Humbug, to reign in the holiday season. The ArtSpace will be transformed into a winter wonderland with wall-to-wall holiday scenes. A lot like traditional German beer halls, there will be long tables and plush banquettes for groups to gather. Bar Humbug will present live musicians and DJs playing the holiday classics. Guests must be 21 to enter.

ZooLights Presented by ComEd and Invesco QQQ will include new and exciting LED light displays,  photo ops, and interactive programming including a never-before-seen garden-themed light show on the zoo’s South Lawn. Festive photo ops will dot the zoo, as well as costumed characters and Victorian carolers on select nights. Food and beverages including festive cocktails and hot cocoa will be available at Edie Levy’s Landmark Café. Snowy’s Sprits & S’more and various snack stations around the zoo. Check the calendar for special events such as sensory-friendly nights, a family-friendly New Year’s Eve celebration, and adults-only evenings. General admission ZooLights tickets are $7 per person. Tickets on Fridays, Saturdays, Thanksgiving Eve (Nov. 22), and New Year’s Eve (Dec. 31) are $10 per person. As part of the zoo’s ongoing commitment to accessibility, general admission is FREE on Mondays. Ticket sales from ZooLights directly support the zoo’s world-class animal care, global conservation efforts, and innovative learning programs and help keep the zoo free to the public 365 days a year. ZooLights will run through January 7, 2024. 

For more information on Chicago holiday happenings, visit Choose Chicago.