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.
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.
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.