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. 

Summer in the City: Chicago’s Theater & Performing Arts

Broadway In Chicago is proud to produce the following shows as part of its summer roster: 

  • Haestown (playing June 20 – 25, 2023, at the CIBC Theatre), winner of eight 2019 Tony Awards® including Best New Musical and the 2020 Grammy® Award for Best Musical Theater Album, is an acclaimed new show from celebrated singer-songwriter Anaïs Mitchell and innovative director Rachel Chavkin. Following two intertwining love stories — that of young dreamers Orpheus and Eurydice, and that of King Hades and his wife Persephone — HADESTOWN invites audiences on a hell-raising journey to the underworld and back. Mitchell’s beguiling melodies and Chavkin’s poetic imagination pit industry against nature, doubt against faith, and fear against love. 
  • MJ (playing August 1 – September 2, 2023, at the James M. Nederlander Theatre), is the multi Tony Award®-winning new musical centered around the making of Michael Jackson’s 1992 Dangerous World Tour. Created by Tony Award®-winning Director/Choreographer Christopher Wheeldon and two-time Pulitzer Prize winner Lynn Nottage, MJ goes beyond the singular moves and signature sound of the star, offering a rare look at the creative mind and collaborative spirit that catapulted Michael Jackson into legendary status.
  • To Kill A Mockingbird (playing August 8 – 13, 2023, at the CIBC Theatre), Academy Award® winner Aaron Sorkin’s new play directed by Tony Award® winner Bartlett Sher and based on Harper Lee’s classic novel, will come back to Chicago as part of a multi-year national tour across North America. Set in Alabama in 1934, Harper Lee’s enduring story of racial injustice and childhood innocence centers on one of the most venerated characters in American literature, small-town lawyer Atticus Finch. 

Chicago Shakespeare Theater will present Disney’s Beauty and the Beast (July 13 – August 20, 2023) at the Courtyard Theater this summer, based on the Academy Award® -winning Disney film and featuring such  dazzling production numbers as the beloved title song and “Be Our Guest.”

The Chicago Symphony Orchestra continues its 2023 season with the following standout events: 

  • Concert for Chicago (June 27, 2023) – Celebrate Zell Music Director Riccardo Muti’s remarkable tenure with the Chicago Symphony Orchestra at this free concert in Millennium Park. Enjoy performances of the heartfelt Andante moderato, written by longtime Chicago resident Florence Price, and Tchaikovsky’s exhilarating Fifth Symphony as the CSO closes the 2022/23 Season in style.

The Tony Award-winning Goodman Theatre concludes its 2022-2023 season with:

  • The Who’s Tommy (June 13 – July 23, 2023): Myth and spectacle combine in a fresh reinvention of The Who’s exhilarating 1969 rock concept album, Tommy—including the unforgettable anthems “I’m Free,” “See Me, Feel Me,” “Sensation,” and “Pinball Wizard.” After witnessing his father shoot his rival, the young Tommy Walker is lost in the universe, endlessly and obsessively staring into the mirror. An innate knack for pinball catapults him from reticent adolescent to celebrity savior. Tony Award-winning composer Pete Townshend and Tony Award-winning original director Des McAnuff find powerful resonance reexamining this classic story for today.

The Joffrey Ballet is pleased to announce an evening of free public performances on June 25, 2023, in the heart of downtown Chicago at the Jay Pritzker Pavilion in Millennium Park. Created as a gift to all Chicagoans, and the first event of its kind, The Joffrey Ballet’s Joffrey for All Celebrationwill feature dance workshops in the lawn and performances by Joffrey Company Artists, the Joffrey Academy of Dance, and students from the Joffrey Community Engagement programs.

Lookingglass Theatre welcomes Lucy and Charlie’s Honeymoon (May 24 – July 16, 2023), which tracks a young couple as they rev it down quintessentially American highways and across stereotypic borders, fleeing expectation and trawling up trouble along the way. Fresh from his Broadway debut in “Almost Famous The Musical”, Artistic Associate Matthew C. Yee’s world premiere musical romp gives a nod to America’s past, takes tally of its present, and blows its future wide open.

Steppenwolf Theatre Company concludes its 2022/2023 season with: 

  • Another Marriage (June 15 – July 23, 2023): Another Marriage is an intimate and beautifully rendered portrait of an ever-evolving relationship that may never be quite finished. Ensemble member Kate Arrington’s playwriting debut upends time and the typical romantic comedy to explore the liabilities of falling in and out of love.
  • No Man’s Land (July 13 – August 20, 2023): In the drawing room of his stately Hampstead mansion, the wealthy, aging Hirst hosts his newfound acquaintance, the enigmatic Spooner, for an evening of endless beer, scotch, and vodka. The night winds on, the drinks keep pouring, and the ground keeps shifting—until two sinister younger men arrive and interrupt the bacchanal. Steppenwolf returns to Harold Pinter’s modern masterpiece: a generational power struggle, a tug of war between expert wordsmiths, a maze of murky meaning. Or perhaps it’s just two old English sots waxing nostalgic and waiting for the sun to rise. In No Man’s Land, you can never be certain, and nothing is as it seems.

Spring Time Chicago: Theatre & Performing Arts 

Choose Chicago

Chicago’s Black Ensemble Theater announces its 2022 Season of Excellence: The Season of Healings with four World Premiere musicals showcasing the power of healing, each featuring different journeys and a variety of genres including gospel, spiritual, soul, jazz, hip-hop, blues, the sounds of the Harlem Renaissance, and more. All performances will be held at the Black Ensemble Theater Cultural Center. The first musical, It’s Just Like Coming to Church, will run from March 20-April 24, 2022. 

Chicago Opera Theater (COT), Chicago’s foremost producer of contemporary and re-imagined opera, proudly presents the World Premiere of the newly commissioned opera Quamino’s Map. Set in post-Revolutionary War England, the work sheds light on the oft-overlooked moment in history when London was the unlikely refuge for thousands of Black Americans who fought for their liberty on the side of the British. Quamino’s Map, the final production of the COT 2021-22 season, will be staged at the Studebaker Theater in the Fine Arts Building for three performances only: April 23, 29 and May 1, 2022.

  • On May 29, 2022, the concert Aretha Rising will pay tribute to the Queen of Soul, Aretha Franklin, as Maestro Speck conducts Broadway star Capathia Jenkins. The program will include Respect, Think, A Natural Woman, Chain of Fools, Amazing Grace, and many more.

Broadway in Chicago

Broadway In Chicago is proud to announce the following shows: 

  • The North American tour of Moulin Rouge! The Musical, winner of 10 Tony Awards –  including Best Musical, will play at the James M. Nederlander Theatre, with performances running from March 19-May 14, 2022. 
  • After taking Broadway by storm, SIX makes a triumphant return to Chicago this spring at the CIBC Theatre from March 29-July 3, 2022. From Tudor Queens to Pop Princesses, the SIX wives of Henry VIII take the mic to remix five hundred years of historical heartbreak into an exuberant celebration of 21st-century girl power!
  • THE PROM is a new musical comedy about big Broadway stars on a mission to change the world and the love they discover that unites them all, comes to the Cadillac Palace Theatre from April 19-24, 2022. 
  • Go behind the music and inside the story of Frankie Valli and The Four Seasons in the Tony and Grammy Award-winning true-life musical phenomenon, Jersey Boys, will play at the Cadillac Palace Theatre from May 3-8, 2022. 
  • All rise for Academy Award winner Aaron Sorkin’s adaptation of Harper Lee’s Pulitzer Prize-winning masterwork To Kill a Mockingbird, which will play from May 17-29, 2022 at the James M. Nederlander Theatre.
  • Tony-winning director Bartlett Sher and the team behind South Pacific, The King and I and 2017 Tony-winning Best Play Oslo, bring a fresh and authentic vision to this beloved theatrical masterpiece Fiddler on the Roof, from Tony winner Joseph Stein and Pulitzer Prize winners Jerry Bock and Sheldon Harnick. Performances will run from May 17 – 22, 2022 at the Cadillac Palace Theatre.

All’s Well That Ends Well, Shakespeare’s vivid exploration of courtship and class comes to new life in the uniquely intimate setting of the Chicago Shakespeare Theater’s Courtyard Theater from April 22-May 29, 2022, staged by acclaimed director Shana Cooper. Besotted with a man who does not return her love, the intelligent, resourceful young Helena navigates the complexities of unrequited romance, courtly drama, and the meddling of elders—only to discover the reality that happy endings are never quite as simple as they seem in fairy tales.

Goodman Theater

The Tony Award winning Goodman Theatre will stage the following during the 2021/2022 season:

  • In Good Night Oscar, Emmy Award-winning actor and producer Sean Hayes (Will & Grace) stars as the irrepressible Oscar Levant. Good Night, Oscar explores the nexus of humor and heartbreak, the ever-dwindling distinction between exploitation and entertainment, and the high cost of baring one’s soul for public consumption. Playing at Goodman’s Albert Theatre, from March 12 – April 17, 2022.

Joffrey Ballet

The Joffrey Ballet kicks off its first performances of 2022 with a spring double-bill featuring Cathy Marston’s world premiere adaptation of Of Mice and Men (April 27-May 8, 2022), Steinbeck’s tender tale of friendship, perseverance, and sacrifice, with an original score by Academy Award®-nominated composer Thomas Newman, along with the Joffrey premiere of George Balanchine’s Serenade, the choreographer’s first ballet created in America in 1934.

Lyric Opera of chicago

Lyric Opera of Chicago’ new-to-Chicago production of Tosca by Giacomo Puccini will run March 12-April 10, 2022, followed by Fire Shut Up in My Bones, playing March 24-April 8, 2022, based on New York Times columnist Charles M. Blow’s widely acclaimed memoir of his traumatic youth growing up in Louisiana. With an amazing collection of talent – composer Terence Blanchard, librettist Kasi Lemmons and a top-flight cast including many of America’s most brilliant singing actors – Fire Shut Up in My Bones is an opera for today, revealing the Black experience in this country as few other operas have done. 

Steppenwolf Theatre Company

The celebrated Steppenwolf Theatre Company returns after a 20-month intermission, with the opening of the $54 million Liz and Eric Lefkofsky Arts and Education Center, which includes the Ensemble Theater in Honor of Helen Zell, an intimate state-of-the-art 400-seat theater in the round, and is topped off by The Loft, an arts and education center for young performers 

  • The winner of eight Tony Awards, including Best Musical, Porchlight’s production of Spring Awakening (April 23-May 29, 2022) tells the timeless story of youthful self-discovery and budding sexuality as seen through the eyes of three teenagers in provincial late 19th-century Germany. 
  • Additionally, Steppenwolf Theatre Company and Center Theatre Group will present the world premiere of the highly anticipated King James by ensemble member Rajiv Joseph, running from March 3-April 10, 2022. “King” LeBron James’s reign in Cleveland brings promise, prosperity and renewal to a city in desperate need of all three. It also brings together two childhood friends who communicate best when they are talking and arguing about the star player’s impact on Cleveland, from his rookie season to the city’s historic championship. Though LeBron James is never seen in the show,  King James is an intimate exploration of the symbolic place that sports and athletes occupy in our emotional lives and relationships.

Chicago Opera Theater’s world premiere of Quamino’s Map in April 2022, followed by the world premiere of new musical Skates (from May 24-August 28, 2022). Also returning to the Studebaker stage next year are performances from Chicago Youth Symphony Orchestras and Chicago Jazz Orchestra.

Teatro ZinZanni is back with a brand-new show starring veteran performer, Frank Ferrante. An experience unlike any other, Teatro ZinZanni is a whirlwind of international cirque, comedy and cabaret, with world-class acrobats, musicians, divas, illusionists, madmen, and aerialists filling the intimate Spiegeltent ZaZou, a unique jewel box mirror tent located in the heart of Chicago’s Downtown Theater District. Tickets can be purchased with or without the featured four-course gourmet feast including a fabulous à la carte cocktail menu, wine & beer list, and special occasion treats. 

Windy City Playhouse

  • SONS OF HOLLYWOOD will be the Windy City Playhouse’s first production back at their flagship location (3014 W. Irving Park Rd.), running from January 26 – April 17, 2022. At the start of the 1920s when Hollywood brimmed with risqué films, enormous parties, and glamorous opening nights, silent film stars Ramon Navarro and William Haines enjoyed life as Hollywood royalty. But when the Motion Picture Production Code brings an end to the no-holds-barred attitude of Hollywood and its acceptance of its gay stars, both men are forced to grapple with their identity in a suddenly oppressive world. Audiences will find themselves immersed in the lavish and dramatic world of a film come to life with a signature 360-degree design and two types of seating: “House” (movie-theater style) and “Top Shelf” (swivel, club-style chair).

Year of Chicago Dance

In partnership with the local dance community, Mayor Lori E. Lightfoot and Department of Cultural Affairs and Special Events (DCASE) Commissioner Erin Harkey have just announced the designation of 2022 as the “Year of Chicago Dance”, a yearlong collaborative initiative which will activate Chicago’s dance industry to address critical issues facing dancers and showcase dance performances, social dancing, and special events for the public in dozens of venues throughout the city. 

Partners will include dance service organizations Chicago Black Dance Legacy Project, Chicago Dancemakers Forum, and See Chicago Dance — as well as Art on theMART, Night Out in the Parks at the Chicago Park District and many other presenters and funders.

Cultural Dance

Cultural dance organizations like Ensemble Español, Muntu Dance Theatre and Mandala Arts will also participate as part of the Chicago dance scene. 

Ensemble Espanol, a premier dance company originating from Albany Park gears up for it’s spring performance at Dominican University, April 23, 2022 7:30 PM.  The program includes the critically acclaimed “Danza del Fuego” (Dance of Fire) choreographed by the Ensemble’s founder, Dame Libby Komaiko, to the music of Ruiz de Luna in the Neo-Classical (Flamenco and Classical) styles. The program also features the Flamenco full company work “No Me Olvides” (No Not Forget Me) by artistic director, Irma Suarez Ruiz, along with her full company classical work, “Balle de Luis Alonso” (Dance of Luis Alonso) to the music of Geronimo Gimenez. Other highlights of the program include “Al Golpe” (To the Beat) and “Ritmo de la Tierra” (Rhythm of the Earth) choreographed by Nino de los Reyes, the first dancer to ever win a Grammy.

Get up and groove with Mandala Arts, the South Loop neighborhood’s cultural gem, specializing in South Asian dance and offering a variety of dance classes year around. Their newest offering, Seniors Dance & Movement, is a virtual fitness class for all with simple and energizing stretches. Dance and movement are set to nostalgic Bollywood grooves. Inspired by iconic South Asian folk and classical dance traditions and designed to keep bodies and minds limber and uplifted. Movements can be done from a seated or standing position.