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. 

29 Reasons to Visit Chicago This Holiday Season

Halloween is so over and now is the time to move on to the magic of Chicago during the holiday season. From skating rinks, tradtional Christmas Markets to show-stopping parades, there’s plenty to enjoy. Here’s some of Choose Chicago’s tips on what to see and do

See the Lights

  • Lightscape, the acclaimed holiday event, returns from November 11, 2022 – January 8, 2023 with a new path and new light-filled installations created just for the Chicago Botanic Garden. Featured artistic works will include favorites such as the luminous Winter Cathedral and a reimagined fire garden. Tickets start at $32 for adults ($30 for members), $16 for children ($14 for child members) and all little ones under 2 can enter for free. 
  • The City of Chicago’s “official” Christmas tree in Millennium Park will shine brightly near the intersection of Michigan Ave. and Washington St. from November 18, 2022 through January 8, 2023. A pre-show will begin at 5 p.m. (with performers including the cast of Cabaret ZaZou and several Broadway in Chicago productions), followed by the lighting at approximately 6:30 p.m. and culminating in a fireworks show. 
Photo credit: Phil Parcellano
  • The annual, one-of-a-kind holiday experience ZooLights (Presented by ComEd and Invesco QQQ) at Lincoln Park Zoo will return from November 19, 2022 – January 1, 2023. Tickets are now on sale for $5 General Admission, Members-only Nights and Sensory-friendly Night. Tickets to Free Admission Mondays will be released the Tuesday prior at 11 a.m. each week.
  • Illumination: Tree Lights at The Morton Arboretum returns for its 10th year during Morton Arboretum’s 100th anniversary year, from November 19, 2022 – January 7, 2023, Explore 50 acres of the Arboretum’s majestic trees during this one-of-a-kind spectacle of color, light, and sound featuring six dazzling new displays as well as returning favorites. You will be awed and delighted by the first-ever Illumination display in the Arboretum’s new Grand Garden, leading to a spectacular laser-light finale. Craft beer lovers won’t want to miss IllumiBrew, November 17-18. This 21-and-over event provides a first look at Illumination while sampling local brews along the trail. New this year is a special series of Electric Illumination late-night experiences (December 16, 23 and 30; 9:30-11:00 PM) for adults 18+ with an eclectic, curated mix of Trance and Progressive House music, synchronized to the light displays. Ilumination ticket costs will run between $11-$22 for members and $16-$27 for guests, depending on the date and other available discounts.
  • Navy Pier’s Light Up The Lake returns from November 25 2022 to January 7, 2023. Visitors can experience the magic with interactive light displays, a whimsical skating rink, journeys through the birch tree maze, visits with Santa, and more. Pricing is $27 for an adult ticket, and 17 for a child’s ticket (ages 3-12).
  • In the nearby suburbs, Brookfield Zoo is hosting their annual Holiday Magicdisplay, a local tradition for more than 40 years. Zoo-goers can stroll along the many pathways lit with more than two million twinkling LED lights, including the 600-foot-long Tunnel of Lights with thousands of colored lights all synchronized to music as well as enjoy a skating rink, illuminated animal sculptures, numerous photo opps, drop-off letters for Santa and more.

Who Doesn’t Love a Parade?

  • The holiday season in Chicago officially kicks off with The Wintrust Magnificent Mile Lights Festival (November 19, 2022) a day-through-night, mile-long extravaganza drawing more than one million celebrants. Its centerpiece is the largest nighttime parade in the U.S. — a spectacular parade down Michigan Avenue. Led by Mickey Mouse and Minnie Mouse of The Walt Disney World Resort, the parade features fabulous floats, giant helium balloons, marching bands, celebrities, musical performances, Santa Claus, fireworks and more —illuminating one million lights on The Avenue’s 200+ trees. Broadcast on ABC 7 Chicago on Sunday, November 20, 2022, Lights Festival will also air throughout the holiday season.
  • The Chicago Thanksgiving Day Parade promises a fun-filled morning in the heart of downtown Chicago on November 24, 2022. Starting at iconic State Street in the Loop at 8:00 AM, the procession makes its way up State from Ida B. Wells Drive to Randolph Street. This free, all-ages event features more than 100 floats filled with entertainers, performance artists, helium balloons led by Teddy the Turkey (the parade’s official mascot) and a visit from Santa Claus.

Find That Perfect Gift

  • The Christkindlmarket Chicago, the most authentic traditional holiday market of its kind outside of Europe, returns November 18, 2022 and runs through the Christmas season, with the main location at Daley Plaza, along with outposts in Wrigleyville and Aurora. Of-age visitors can enjoy a mug of glühwein (hot spiced wine) as well as sweet and savory German snacks while shopping for handmade and traditional souvenirs. There are also musical performances and plenty of family-friendly activities for kids.
  • Now in its 21st year in Chicago, the One of a Kind Holiday Show (December 1-4, 2022) brings together hundreds of talented artists, makers and designers with thousands of happy shoppers who love art and original work. The show continues to be the best place in Chicago to find thousands of handmade products, truly unique and meaningful gifts for the holidays.
  • At the iconic Macy’s on State Street, take a break from holiday shopping to enjoy the annual Holiday Windows or have a peek at the Great Tree inside the historic Walnut Room, the first restaurant ever opened in a department store. With Circassian wood paneling imported from Russia and Austrian chandeliers, the 17,000 square foot dining room is both elegant and comfortable and a favored place to enjoy a festive afternoon treat.

Enjoy a Holiday Exhibit

  • At the Museum of Science and Industry (MSI), the annual Christmas Around the World and Holidays of Light exhibits return November 16, 2022-January 4, 2023. A simple tradition that began in 1942 with a single tree now features a four-story, floor-to-dome Grand Tree, surrounded by a forest of more than 50 trees and displays decorated by volunteers to represent the holiday traditions from cultures around the globe.

Lace Up Your Skates

  • The scenic rink at Millennium Park offers panoramic views of Cloud Gate (aka “The Bean”) and the surrounding city skyline dusted in snow. The rink is open daily from November through March, weather permitting. Skate rentals are available, or you can bring your own.
  • Nearby, Maggie Daley Park is known for its one-of-a-kind Skating Ribbon, an icy path that curves through the park’s whimsical landscape. The Skating Ribbon is open from November through March. You can reserve skate rentals ahead of time or use your own.
  • The Gallagher Way Rink in Wrigleyville offers ice skating from November 18, 2022 – January , 2023, weather permitting. The Rink welcomes all skill levels to skate on their own or ride ice bumper cars on the newly expanded 12,000 square-foot ice rink, located inside Wrigley Field. Tickets are required for access and may be booked ahead of time here or on site. Activities at Gallagher Way also include holiday movie nights, a wreath-making workshop, a branch of Chicago’s Christkindlmarket and meetings with Santa.

Catch a Festive Live Show

Hotel Happenings 

The Peninsula Chicago is back with the Merry & Bright Holiday Package (ideal for couples) and Holly Jolly Family Holiday Package (great for families), valid for stays from November 26 – December 31, 2022. Guests are also encouraged to make a reservation for The Peninsula Hotel’s Holiday Afternoon Tea, where the 20-foot Christmas tree and lavish holiday décor at The Lobby enhance the traditional English tea menu of finger sandwiches, scones with house made preserves and Devonshire clotted cream, and petite seasonal pastries. Vegan and gluten-free options are available. 

The Langham Chicago is again offering its traditional Thanksgiving Feast on November 24, 2022 at its onsite restaurant Travelle, where the menu curated by Executive Chef Damion Henry includes holiday favorites, turkey and stuffing, as well as complementary enhancements such as seafood and carving stations. Chef Henry is also preparing a Christmas Day Brunch on December 25, 2022 and afternoon tea is available throughout the holiday season. 

The Pendry Chicago is offering a series of seasonal happenings, from a “Friendsgiving” dinner at onsite restaurant Venteux on November 23, 2022 to lighting the Menorah each night at 5 p.m. from December 18 – December 26, 2022 to Christmas Eve Dinner and Christmas Day brunch at Venteux on December 24 and 25, 2022.

Grab your partner and head to The Emily Hotel for the ultimate winter rooftop curling experience, complete with an overnight stay for two, curling for two players and two complimentary cocktails at Stone’s Throw. Stone’s Throw, located on the fifth floor of the hotel, features four Olympic sized curling rinks and heated yurts decked out in 80s nostalgia serving up a menu of winter sips and snacks. Offer valid for reservations of 1 or more nights booked by March 27, 2023 for stays between November 11, 2022 and March 31, 2023.

Celebrate winter at Fairmont Millennium Park Chicago’s Fairmont Lodge where you can relax, recharge and have fun with their cozy decor, indoor “fire pits”, festive programming, overnight packages and more. 

The annual Winter Wonderland returns to the IlO Godfrey Rooftop at The Godfrey Hotel with its heated, clear-domed igloos which are available to rent (for groups of up to six people) with purchase from the menu. Order a hot cocktail and s’mores to roast over the outdoor firepits and enjoy winter in Chicago under the city lights. 

From November 1 through January 3, LondonHouse Chicago is hosting Rudolph’s Rooftop from November 1, 2022 – January 3, 2023. This fun holiday-themed experience, complete with whimsical decor, photo opps and igloos, takes place on the 22nd level terrace, featuring breathtaking panoramic views of the city. Holiday cocktails are available from Executive Chef Elizabeth Sweeney.