Chicago Loop Alliance releases ‘Holidays In The Loop’ List Highlighting Festive Activities For 2019

(CHICAGO)—In order to ensure Chicagoans and visitors enjoy the holiday season to the fullest, Chicago Loop Alliance has once again launched “Holidays in the Loop.” Businesses and attractions in the Loop and beyond are featured in printed pocket guides distributed around the city and suburbs; three State Street CTA kiosks; and through digital and social media channels.

For ideas on how to make the most of the holidays in Chicago’s official downtown, check out the listings below. For more details, visit

Holiday Events

What: 106th Annual Chicago Christmas Tree Lighting Ceremony
When: 6 p.m. on Nov. 22
Where: Millennium Park, Wrigley Square, Michigan Ave. & Randolph St.
Description: Enjoy the glittering tree set among Chicago’s sparkling skyline and the iconic art and architecture of Millennium Park at this free tree lighting event.

What: Absolutely Chicago Segway Tours’ Holiday Lights Segway Tour
When: Nov. 22-Dec. 22
Where: 300 E. Monroe St.
Description: Get into the Spirit on a 2-hour holiday Lights Tour. Explore the Loop, Michigan Avenue and Christkindlmarket while gazing at millions of Christmas lights. Chicago comes alive during the holidays, the trees twinkle under the blankets of a millions lights. See the iconic “Bean” as you roll along Michigan Avenue gazing at the ice skaters on your way to view the famous holiday window displays on State Street. Musicians play festive tunes on every corner, as we celebrate the happiest time of year. There is no better way to get into the spirit of the season than explore Chicago in its holiday splendor on a segway.

What: Millennium Park Holiday Art Market with School of the Art Institute of Chicago and Columbia College Chicago
When: 11 a.m.-7 p.m. Nov. 22-23, 11 a.m.-5 p.m. Nov. 24
Where: Millennium Park, Chase Promenade North
Description: Start your holiday shopping with one-of-a-kind items, including jewelry, fashion, painting, sculpture, prints, drawings and more on sale by student artists at this free event. The Holiday Art Market is supported by the Millennium Park Foundation.

What: Chicago Thanksgiving Day Parade
When: 8-11 a.m. Nov. 28
Where: State Street in the Loop
Description: The Chicago Thanksgiving Day Parade kicks off the holiday season with a fun-filled morning in the heart of downtown Chicago. Watch the colorful procession make its way up State from Ida B. Well Drive to Randolph Street at this free, all-ages event. Originating in the 1930s, when it was called the Christmas Caravan, the parade was created to help lift the spirits of those suffering through the Great Depression. It continues to raise spirits to this day.

What: Caroling at Cloud Gate
When: 6 p.m. on Nov. 29 and Dec. 6, 13 and 20
Where: Millennium Park, Cloud Gate, 201 E. Randolph St.
Description: Bundle up and belt out some holiday classics as local Chicago choral groups lead hundreds of celebrants in song at this free event.

What: Dance-Along Nutcracker
When: Dance lessons at 11 a.m. and 2 p.m., performances at noon and 3 p.m. Dec. 8
Where: Chicago Cultural Center, 78 E. Washington St.
Description: Sugar plum fairies and mouse kings of all ages and abilities are invited to point their toes to the familiar music of Tchaikovsky’s holiday classic at this free event. The Dance-Along Nutcracker, created in 1985, is the property of the San Francisco Lesbian/Gay Freedom Band, the world’s first openly gay musical organization.

What: Maggie Daley Park Skating Ribbon & Skate with Santa
When: Skate with Santa Dec. 14
Where: 337 E. Randolph St.
Description: In the heart of the Loop, with the city’s skyline as a backdrop, a ribbon of ice winds through a rolling landscape providing an ice skating experience unlike any other. The skating ribbon is dramatically different from typical civic ice rinks, creating a multisensory activity that is integrated into the landscape. Skaters can experience “alpine in the city” as they lace up their ice skates and follow a path twice the length of a lap around a traditional skating rink. Complementing the ribbon are places to enjoy a cup of hot chocolate and rent skates.

Performing Arts

What: “Twice, Thrice, Frice”
When: Through Nov. 10
Where: Silk Road Rising, 77 W. Washington St.
Description: In this 100-minute comedy, three Muslim women confront adultery and polygamy when one of their husbands marries a second wife. Friendship, fidelity and faith are called into question as each woman reevaluates bonds once believed unbreakable, and discovers humor amongst the heartbreak.

What: “Hamilton”
When: Now playing through Jan. 5, 2020
Where: CIBC Theatre, 18 W. Monroe St.
Description: “Hamilton” is the story of America’s Founding Father Alexander Hamilton, an immigrant from the West Indies who became George Washington’s right-hand man during the Revolutionary War and was the new nation’s first Treasury Secretary. Featuring a score that blends hip-hop, jazz, blues, rap, R&B and Broadway, “Hamilton” is the story of America then, told by America now.

Where: Spiegeltent ZaZou, Cambria Hotel, 32 W. Randolph St.
Description: Teatro ZinZanni is a whirlwind of international cirque, comedy and cabaret served with a multi-course feast. Described as the “Kit Kat Klub on acid,” the fast-paced action unfolds around, above and alongside guests as world-class acrobats, musicians, divas, illusionists, madmen and aerialists fill the intimate Spiegeltent ZaZou, a unique jewel box mirror tent. Teatro ZinZanni’s signature blend of Love, Chaos & Dinner has played to sold out audiences in Seattle and San Francisco. Don’t miss the show The New York Times calls, “A feast for the senses” and the “city’s hottest ticket.”

What: Macy’s State Street Holiday Windows
When: November-December
Where: 111 N. State St.
Description: Since the early 1870s, Macy’s has been stunning spectators with its famed holiday window displays and celebratory events. Macy’s was the first store to feature holiday windows created for the pure fun and joy of the season and, with that, began a tradition that still lives on today.

What: Imaginative animated video installation
Where: DePaul University, 247 S. State St.
When: November-December
Description: The School of Cinematic Arts at DePaul University is creating a new annual Christmas tradition reminiscent of the fabled Christmas windows that once lined downtown State Street. Created by animation and production design faculty and students, the Merry Christmas from DePaul window will utilize state-of-the-art technology to build an imaginative, 3-D experience rooted in sharing the magic of Christmas and evoke a sense of communal joy this time of year.

What: Christkindlmarket
When: Nov. 15-Dec. 24
Where: Daley Plaza, 50 W. Washington St.
Description: The Christkindlmarket Chicago has been a beloved holiday tradition in the heart of the city since 1996. The outdoor market is always free of admission. Visitors can enjoy 40 days of holiday fun at the most authentic outdoor market of its kind outside of Europe. This year, 55 vendors from all around the world sell local and international food, beverages and merchandise.

What: “A Christmas Carol”
When: Nov. 16-Dec. 29
Where: Goodman Theatre, 170 N. Dearborn St.
Description: A timeless holiday tradition, the Goodman’s production of “A Christmas Carol” celebrates the yuletide season by infusing Charles Dickens’ classic tale with a little bit of magic, as only the Goodman can. From amazing flying ghosts to a quiet little boy and his crutch, “A Christmas Carol” is filled with enough singing, dancing and enchantment to rejuvenate even the most disheartened of spirits. Audiences will delight as the cast helps transform the miserly Ebenezer Scrooge through the course of one very memorable Christmas Eve.

What: “Chicago Celebrates Sondheim!”
When: Nov. 16
Where: Auditorium Theatre, 50 E. Ida B. Wells Drive
Description: The Auditorium Theatre presents “Chicago Celebrates Sondheim!” commemorating the legendary composer and lyricist ahead of his 90th birthday. Directed and produced by cabaret star Joan Curto, the evening features jazz, pop, folk, theater, and classical performers putting their own spin on songs from classic musicals like “Follies,” “Company,” “Sweeney Todd,” “Sunday in the Park with George,” “Into the Woods” and more.

What: Bobby’s Bike Hike’s Holiday Hike
When: Nov. 18-Dec. 24
Where: 540 N. Lake Shore Drive
Description: When we think of the winter holidays, two things come to mind: festive decorations and an excess of food. You can’t celebrate the holidays with one and not the other, which is why our “Holiday Hike: Season Sampling Walking & Food Tour” has both. Let Bobby’s Bike Hike show you how downtown Chicago gets gussied up even more than usual, from the window displays at Macy’s (a 70+ year tradition), to the German open-air Christkindlmarket, to the official 106th City of Chicago Christmas Tree. As your eyes feast on all the decorations, you’ll be feasting on some Chicago holiday classics. We’ll start with deep dish pizza from Giordano’s and then sip on seasonal hot cider that’ll be served with double stuffed German bratwurst at the Christkindlmarket. For dessert, we’ll walk to the Palmer House, the birthplace of the first brownie. They’ve been using the original recipe for over 100 years.

What: “’Twas the Night Before…” by Cirque du Soleil
When: Nov. 29-Dec. 8
Where: The Chicago Theatre, 175 N. State St.
Description: “’Twas the Night Before…” is an exhilarating new spin on the beloved Christmas classic as only Cirque du Soleil can imagine. This vibrant acrobatic show about the joy of sharing and friendship promises to spark lasting memories in the hearts of children and adults alike. Expect the unexpected. Find out what really happened before Santa dropped in.

What: The Joffrey Ballet’s “The Nutcracker”
When: Nov. 30-Dec. 29
Where: Auditorium Theatre, 50 E. Ida B. Wells Drive
Description: Choreographer Christopher Wheeldon’s acclaimed turn-of-the-century tale opens on Christmas Eve, 1892, mere months before the grand opening of the 1893 World’s Fair, as young Marie and her mother prepare for a Christmas Eve potluck celebration. The magic of the season takes hold when a visit from The Great Impresario sets of a whirlwind journey of romance and adventure through a dreamlike World’s Fair.

What: A&A Ballet’s “The Art Deco Nutcracker”
When: Dec. 6-8
Where: 410 S. Michigan Ave.
Description: Alexei Kremnev’s “The Art Deco Nutcracker” is an original interpretation of the treasured holiday classic that is set in 1920s America and features a choreographic style The Huffington Post has described as “electric” and “echoing with audiences of all ages.” The Chicago Tribune proclaimed it as “a glossy rendition filled with ‘gorgeous, glitzy costumes’ and an ‘impressive cast.'”

What: Irving Berlin’s “White Christmas”
When: Dec. 10-15
Where: Cadillac Palace Theatre, 151 W. Randolph St.
Description: Start with a timeless tale of joy and goodwill, fill it with classic Irving Berlin songs, top it off with glorious dancing and lots of snow and head on over to the Cadillac Palace Theatre to see Irving Berlin’s “White Christmas.” Performances begin Dec. 10 for this must-see classic in a lavish new production that the New York Times says to “put on your wish list.” Irving Berlin’s “White Christmas” tells the story of a song-and-dance team putting on a show in a magical Vermont inn and falling for a stunning sister act in the process. Full of dancing, laughter and some of the greatest songs ever written, give everyone the gift they’re dreaming of with this merry and bright holiday musical.

What: Chicago Symphony Orchestra’s “Merry, Merry Chicago!”
When: Dec. 14-23
Where: Symphony Center, 220 S. Michigan Ave.
Description: Don’t miss Symphony Center’s annual spectacular featuring Members of the CSO, the Chicago Symphony Chorus and special guests performing festive favorites. It’s the perfect celebration for the entire family.

What: “The Phantom of the Opera”
When: Dec. 18-Jan. 5
Where: Cadillac Palace Theatre, 151 W. Randolph St.
Description: Critics are raving that this breathtaking production is “bigger and better than ever before” and features a brilliant new scenic design by Paul Brown, Tony Award-winning original costume design by Maria Björnson, lighting design by Tony Award-winner Paule Constable, new choreography by Scott Ambler, and new staging by director Laurence Connor. The production, overseen by Matthew Bourne and Cameron Mackintosh, boasts many exciting special effects including the show’s legendary chandelier. The beloved story and thrilling score—with songs like “Music of the Night,” “All I Ask Of You,” and “Masquerade”—will be performed by a cast and orchestra of 52, making this “Phantom” one of the largest productions now on tour.

What: “Mean Girls”
When: Dec. 25-Jan. 26
Where: James M. Nederlander Theatre, 24 W. Randolph St.
Description: Direct from Broadway, “Mean Girls” is the hilarious hit musical from an award-winning creative team, including book writer Tina Fey (“30 Rock”), composer Jeff Richmond (“Unbreakable Kimmy Schmidt”), lyricist Nell Benjamin (“Legally Blonde”) and director Casey Nicholaw (“The Book of Mormon”). Cady Heron may have grown up on an African savanna, but nothing prepared her for the vicious ways of her strange new home: suburban Illinois. Soon, this naïve newbie falls prey to a trio of lionized frenemies led by the charming but ruthless Regina George. But when Cady devises a plan to end Regina’s reign, she learns the hard way that you can’t cross a Queen Bee without getting stung.

What: “Too Hot to Handel: The Jazz-Gospel Messiah”
When: Jan. 18 and 19, 2020
Where: Auditorium Theatre, 50 E. Ida B. Wells Drive
Description: Hosted on Martin Luther King, Jr., Day weekend, this is a unique take on Handel’s classic oratorio. Featuring three incredible soloists, an uplifting choir, a fiery orchestra, an electrifying jazz combo and famed Detroit pianist Alvin Waddles, “Too Hot” will have you clapping, singing and dancing in the aisles this holiday season.


What: 360 CHICAGO Observation Deck
Where: 875 N. Michigan Ave.
Description: Located 1,000 feet above Michigan Avenue on the 94th floor of the John Hancock Center. 360 CHICAGO offers breathtaking views of Chicago’s skyline, Lake Michigan, and the surrounding states. It’s also the only place you can enjoy TILT – Chicago’s highest thrill ride. TILT is a one-of-a-kind engineering marvel that tilts visitors over the edge of the 94th floor, providing the most exhilarating views of Chicago. Relax at the observation deck’s BAR 94, offering local favorites from Revolution Brewing and KOVAL Distillery, a large menu of custom cocktails, and front-row seating to the city’s best views from 1,000 feet up.

What: American Writers Museum
Where: 180 N. Michigan Ave.
Description: For a one-of-a-kind Chicago museum experience downtown, visit the American Writers Museum. As one of the most unique Chicago museums downtown, its mission is to celebrate the enduring influence of American writers on history, identity, culture, and daily lives.

What: The Art Institute of Chicago
Where: 3 S. Michigan Ave.
Description: The Art Institute is the second largest art museum in the country with a collection of approximately 300,000 works of art. The Art Institute of Chicago collects, preserves and interprets works of art of the highest quality, representing the world’s diverse artistic traditions, for the inspiration and education of the public and in accordance with the profession’s highest ethical standards and practices. With an annual visitation of about 1.5 million, the Art Institute is one of the most popular attractions for Chicago residents and visitors alike.

What: Chicago Architecture Biennial
When: Sept. 19—Jan. 5
Where: Chicago Cultural Center, 78 E. Washington St.
Description: See exhibitions, performances, films and talks at the 2019 Chicago Architecture Biennial and explore how architecture shapes our communities, cities and environment at this free event. The main exhibition at the Chicago Cultural Center is free and open to the public from Sept. 19, 2019, through Jan. 5, 2020. As the largest exhibition of contemporary art, architecture and design in North America, the third edition of the Biennial features more than 80 contributors from more than 20 countries. More than 40 sites and 100 organizations across Chicago will partner with the Biennial, serving as host venues and producing independent exhibitions and programs throughout the neighborhoods.

What: Chicago Architecture Center
Where: 111 E. Wacker Drive
Description: Don’t miss the highly acclaimed Chicago Architecture Center (CAC), the city’s newest museum and best way to launch your Chicago architecture adventure. See the country’s largest 3D model of Chicago, boasting more than 4,200 buildings and an interactive video. In the skyscraper gallery, walk through super-sized tall building models from around the globe and learn about Chicago’s history of innovation. The CAC also is the starting place for more than 85 tours all led by our highly trained volunteer docents.

What: Gene Siskel Film Center
Where: 164 N. State St.
Description: With a schedule that comes out monthly, and changing on a week-to-week basis, the Gene Siskel Film Center will introduce you to cinema, stories and cultures you would not know of otherwise. As a public program of the School of the Art Institute of Chicago, the Film Center presents an eclectic curated mix of more than 1,500 screenings with 200 guest artist appearances annually to enhance your filmgoing experience.

What: McCormick Tribune Ice Rink
Where: Millennium Park, 1 N. Michigan Ave.
When: Nov. 15-March 2020, weather dependent
Where: Millennium Park
Description: Admission to the rink is free, and skates are available for rent.

What: The Rookery Light Court Tours
Where: The Rookery Building, 209 S. LaSalle St.
Description: Take a guided tour of The Rookery Light Court festively decked for the holidays, complete with a giant tree in the lobby. Learn how Frank Lloyd Wright remodeled Burnham and Root’s landmark 1888 skyscraper. Get an exclusive view of the spectacular oriel staircase. On Mondays and Wednesdays, visit the library where Daniel Burnham and associates hatched plans for the 1893 Columbian Exhibition.

What: Skydeck at Willis Tower
Where: 233 S. Wacker Drive
Description: Skydeck Chicago is the observation deck located on the 103rd floor of the iconic Willis Tower. Along with spectacular views of the city and region, the Skydeck is also home to The Ledge, a series of glass balconies extending 4.3 feet outside the building. In addition, the private dining and event space offers 360-degree views in this world-class venue.


What: Block 37
Where: 108 N. State St.
Description: Block 37 is a hip and urban shopping, dining and entertainment destination, spread out over an entire block in the heart of Chicago’s Loop. Structured around a five-story atrium, Block 37 is home to an ample selection of the best fashion and beauty brands, while also hosting a list of cafes, boutiques and other essential conveniences.

What: Carpe Librum used bookstore
Where: Block 37, 108 N. State St., Pedway level
Description: Have a family member who’s a bookworm? Need a last minute White Elephant gift? Carpe Librum is the perfect place to find a unique and memorable gift for the holiday season. The bookstore has a wide range of books ranging from fiction to history, biographies to cookbooks, art books to children’s books, and many more. It also carries a wide range of CDs and DVDs. Everything is donated and priced under $6. The best part? All proceeds go to family engagement programs in Chicago Public Schools.

What: Merz Downtown
Where: 17 E. Monroe St.
Description: Enjoy an unsurpassed selection of natural health, beauty and personal care, men’s grooming, fine skin care products, and niche fragrance from around the world.

What: Whimsical Candy
Where: 175 N. Franklin St.
Description: Watch your sweet holiday gifts as they’re made at the Loop’s only working candy kitchen. Whimsical Candy specializes in chocolate, caramel, nougat, marshmallow and fruit candies, layered into its signature La-Dee-Dahs swirls and a dozen unique candy bars. They also have nostalgic candy and classic favorites, including a large selection of chocolate covered nuts and malt balls. Send the ‘Whimsy City” to corporate clients, friends and family with gift boxes, available in all sizes, including a Gift Tower large enough for an office.


What: Dealer’s Choice “Naughty or Nice” cocktail
When: Nov. 15-Dec. 31
Where: The Dearborn, 145 N. Dearborn St.
Description: Have you been naughty or nice this year? Stop in to this Loop favorite for the special “Dealer’s Choice” cocktail made according to your tastes. In the heart of Chicago’s Loop, The Dearborn provides a perfect break for visitors of the area’s neighboring theaters, museums, shopping and popular attractions. The Dearborn is open for lunch and dinner seven days a week and brunch on the weekends.

What: Grant Park Bistro
Where: 800 S. Michigan Ave.
Description: Grant Park Bistro, the French bistro on the ground floor of the newly renovated Hotel Essex, is pleased to offer excellent happy hour specials Monday-Friday in their bar along Michigan Avenue. Specials at the French grill from LM Restaurant Group include $4 select draft beers, $6 specialty cocktails and $6 wines by the glass. Diners can also indulge in the restaurant’s signature grilled flatbreads, housemade chicken liver mousse tarte and classic burger.

What: Land & Lake Kitchen
Where: 81 E. Upper Wacker Drive
Description: Land & Lake Kitchen, located at the corner of Michigan and Wacker, serves elevated takes on classic Midwestern dishes. Join Land & Lake Monday-Friday and enjoy great happy hour specials like $4 select draft beers, $6.50 select cocktails and select half-priced wine. Food specials include the restaurant’s signature burger, mac & cheese and three bean Midwestern chili.

What: Latinicity
Where: Block 37, 108 N. State St.
Description: Chef Richard Sandoval combines the warmth of Latin American dining with an authentic and vibrant street food environment at Latinicity Food Hall and Lounge on the third floor of Block 37.

What: Monk’s Pub
Where: 205 W. Lake St.
Description: Check the Monk’s Pub website for tapping events of holiday and winter beers.

What: Santa at the Berghoff
When: Nov. 29 and 30 and Dec. 7, 14, 20, 21 and 23
Where: 17 W. Adams St.
Description: The Berghoff has made it to the nice list 121 years in a row. Make sure you join them this holiday season, as the jolly man himself makes a special appearance. The Berghoff will also once again be hosting a book drive, benefiting the SOS Villages of Illinois. Please drop off new or gently used children’s books or coloring books in the main dining room or lower level toy chest.

What: Skate & Steak
When: Nov. 15-March 8
Where: About Last Knife, Hotel Julian, 168 N. Michigan Ave.
Description: Show your receipt from Millennium Park ice skating to receive 25 percent off your bill at the Hotel Julian’s About Last Knife.

What: Sugar Bliss
Where: 115 N. Wabash Ave. and 122 S. Wabash Ave.
Description: Sugar Bliss has great holiday gifts – macarons, cake pops cupcakes, cookies and more. Make a $25 purchase and get a complimentary hot chocolate or coffee.

What: Wow Bao
Where: 1 W. Upper Wacker Drive
Description: Wow Bao specializes in steamed hot Asian buns with a variety of savory and sweet fillings, perfect for on-the-go. The fast casual spot also features rice and noodle bowls, potstickers, dumpling soup and homemade ginger ale.

About Chicago Loop Alliance

Chicago Loop Alliance’s (CLA) mission is to create, manage and promote high-performing urban experiences, attracting people and investment to the Loop. CLA is a membership organization as well as the sole service provider for Special Service Area#1-2015, and the Chicago Loop Alliance Foundation produces public art projects and events.


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