Celebrate the Holidays in Chicago, Winter 2021

I love Chicago no matter the time of year, but this time of year with all the holiday lights and decorations, the streets and trees dusted with snow, it all takes on such a magical glow. That’s why I was happy when my friend Katie Papadopoulos of Choose Chicago sent me a list–and it’s a long one–of all the special ways to enjoy the city this season.

Visit the traditional Christkindlmarket at Daley Plaza (celebrating its 25th anniversary this year) for a mug of glühwein and that perfect handcrafted gift. Lace up your skates and zip around The Peninsula Sky Rink (the only hotel skating rink in Chicago) followed by a traditional Holiday Afternoon Tea in The Lobby beneath the 20 foot Christmas tree. Marvel at the thousands of twinkling lights on display at ZooLights and Illumination at The Morton Arboretum or the dozens of festively decorated trees at the MSI’s Christmas Around the World display.  Or head over to Navy Pier’s new “Light Up the Lake, an indoor, temperature controlled experience featuring large-scale light-sculpture displays, a regulation-size Alpine ice rink, authentic holiday beer garden, kiddie train rides, Santa’s Village and gift market and other family-friendly events. Winterland at Gallagher Way will extend its festivities beyond the holiday season with ice bumper cars, skating lessons and curling lessons running through January/February 2022 and the popular Maggie Daley Ice Skating Ribbon will return with a fun new collaboration with the blockbuster art experience Immersive Van Gogh, projecting visuals of sunflowers and starry night brush strokes onto the ice. 

Come find out why Chicago was once again designated by Conde Nast Traveler’s readers as the Best Big City in the U.S. in 2021, for the fifth year in a row and check out what’s new in Chicago this holiday season! 

Visit the below links for more information regarding: 

Holiday Attractions & Programming

Attractions:

The holiday season kicks off in Chicago on November 20 with the BMO Harris Bank Magnificent Mile Lights Festival, returning  for the annual Tree-Lighting Parade down North Michigan Avenue with Grand Marshals Mickey and Minnie Mouse from Walt Disney World® Resorts in Florida. The event-filled day begins at 11:00 AM. starting at Lights Festival Lane (401 North Michigan Avenue) with a festive thoroughfare of booths and family activities, including photos with Santa Claus. The parade of fabulous floats, giant helium balloons, exciting marching bands, celebrities, musical performances, Santa Claus, and more begin at 5:30 PM., helping illuminate the more than 200 trees along The Magnificent Mile. 

The City of Chicago’s 108th Christmas Tree lighting in Millennium Park will return November 19, 2021 and shine through the holiday season until January 9, 2022. The festivities begin with a pre-show by DJ Selah Say (5:30-6:00 PM), performances by Mariachi Herencia de Mexico, the cast of Chicago Opera Theater, a youth dance ensemble from the Kenwood School of Ballet and special guests Dreezy Claus and Sister Claus (6:00-6:30 PM), the tree-lighting and fireworks (6:30 PM) and a post-lighting concert featuring  DJ Selah Say, Cirque du Soleil, Chicago Soul Spectacular and singer-songwriter Brian McKnight (6:35-7:45 PM).

Bring the holiday season onto the waters of the Chicago River and Lake Michigan with a series of brunch, lunch and dinner cruises from City Cruises by Hornblower celebrating Thanksgiving, Christmas Eve and New Year’s Eve. Prices range from $60 – $300 and include 2-3 hours of buffet or plated dinner service, spectacular views of the city skyline and local landmarks, onboard entertainment, festive decor, open bar for select cruises or the ability to upgrade your drink menu with creative cocktails, wine and beer. 

The Christmas Around the World and Holidays of Light Exhibits return to the Museum of Science and Industry (MSI) from November 17, 2021-January 3, 2022, an annual tradition that began in 1942 with a single tree and now has expanded to feature 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. This year, MSI is celebrating the golden age of travel with themed décor and a spotlight on the Pioneer Zephyr train and Take Flight’s 727, which have been newly reimagined. Entrance to the exhibits is included in the regular cost of entry with museum admission ($21.95 for anyone Age 12+, $12.95 for any child 3-11) but those who wish to take a picture with Santa in his photo studio inside the Holiday Store must buy a special timed-entry ticket. 

Christkindlmarket, the beloved annual holiday tradition returns for its 25th season this year in Daley Plaza (November 19-December 24, 2021). Modeled after the 16th century holiday markets in Germany, this Christmas bazaar is a hub for traditional German fare, delightfully warm beverages, charming musical performances and charming holiday vibes that the entire family can enjoy. Enjoy a mug of glühwein (traditional hot spiced wine), snack on  currywurst, schnitzel and pretzels and shop for the perfect handmade gift. Another Christkindlmarket will take place at Wrigleyville (November 19-December 31, 2021).

Fairmont Chicago, Millennium Park is thrilled to announce a new winter experience, Fairmont Lodge, debuting for its inaugural winter season starting November 20-February 2022. Completely transforming the hotel’s lounge, Fairmont Lodge celebrates the winter season with cozy décor, fire pits, festive programming, overnight packages and more.  Chef William Schultz completes the experience with a seasonal menu of wintery-themed bites like Sweet and Savory Fondue and S’mores, Oaxaca Spiced Short Ribs and more. Signature hand-crafted cocktails include a Flaming Eggnog made tableside and Oh So Delish Hot Chocolate, both served in a Lodge-themed collector cup. Cozy up to one of Fairmont Lodge’s nine indoor fire pit tables (every Wednesday-Sunday), enjoy weekly Thursday Happy Hours in December and check the calendar for special events. 

The ninth annual Illumination: Tree Lights at The Morton Arboretum returns as a walking experience from November 20, 2021 – January 2, 2022. Visitors can explore 50 acres of the Arboretum’s majestic trees during this one-of-a-kind spectacle of color, light, and sound, and see returning favorites and surprising new sights, including a special Human+Nature display and an experience featuring 150 colorful lanterns. Along the one-mile, paved walking path filled with festive music and lighting effects that highlight the beauty of trees in winter, guests can warm up by a crackling fire and roast marshmallows for s’mores, or stop in one of the concession tents for a snack and beverage. Advance purchase is recommended as many nights will sell out.

  • IllumiBrew returns for two nights (November 18 and 19), a special event where an ages 21+ crowd can sample seasonal beers, ciders, and meads from popular Chicagoland breweries stationed along the Illumination trail; each tasting ticket includes fifteen 3 oz beer samples and a souvenir light up tasting glass. 

Navy Pier’s “Light Up the Lake will open on November 26, 2021 and run through January 2, 2022. This indoor, temperature controlled experience will feature large-scale light-sculpture displays (more than 600,000 twinkling lights), a regulation-size Alpine ice rink, authentic holiday beer garden, kiddie train rides, Santa’s Village and gift market and other family-friendly events. Every ticket also comes with a free ride on the Centennial Wheel. Light Up the Lake will also offer sit-down dining with holiday-themed eats, signature cocktails, and seasonal brews.

Santa Baby Bar, opening November 17, 2021, returns for the holiday season with a multi-room, multi-level, over-the-top Christmas experience. All guests must reserve online, for no more than six people, and all tables are limited to no more than ninety minute intervals. 

Returning for its ninth season, The Peninsula Sky Rink (2,100 sq ft) is the only hotel skating rink in Chicago, located above Chicago’s bustling Michigan Avenue. Surrounded by Chicago’s skyscrapers and twinkling lights, the rink is tucked into a pine tree winter wonderland and bathed in festive music and snowflake lighting. The skating rink’s outdoor menu features a selection of hot beverages and snacks including hot chocolate, hot cider, and other treats, and is available for groups to rent or for private events. All monies collected include skate rental ($20 for adults and $10 for children 12 and under) and are donated to Ann & Robert H. Lurie Children’s Hospital of Chicago, and Hephzibah Children’s Association.

Winterland at Gallagher Way (November 19, 2021 – February 20, 2022)  will include a ceremonial tree lighting (November 29, 2021), ice skating on an 8,000 square-foot ice rink,Santa’s Workshop, wreath making workshops (December 4-5, 2021), holiday movie screenings (Thursdays in December 2021) and special programming at Hotel Zachary (weekends in November-December, 2021). New to this year’s transformation will be a special celebration of Hanukkah (December 5, 2021), ice bumper cars and skating lessons (January 2022) and curling lessons (February 2022). 

The popular Winter Wonderland returns to The Godfrey Hotel’s I|O Rooftop Lounge. The heated, clear-dome igloos on the rooftop’s outdoor portico will make guests feel like they are in their own personal snow globe. Order a hot cocktail and s’mores to roast over the outdoor firepits and enjoy winter in Chicago under the city lights. 

  • Minimum required to reserve one of the smaller (6-person) igloos is one bottle while the minimum for a larger igloo is $500. Due to extremely high demand igloos are only available for a two-hour window and fully close by 11PM (8PM on Sundays). 

ZooLights at the Lincoln Park Zoo, Chicago’s favorite holiday tradition, is back and better than ever (from November 19, 2021-January 2, 2022) with a new Pepper Family Wildlife Center at the heart of the zoo, a new holiday lights experience on the Main Mall, and an exciting new light show on the South Lawn. Also new this year: sensory-friendly visit times and an impressive 18-foot holiday tree sure to inspire festive oohs and aahs. Tickets are $5 per person (free admission on Mondays and Tuesdays).

Holiday Meals:

Guests at The Peninsula Chicago can enjoy Holiday Afternoon Tea in The Lobby beneath the 20-foot Christmas tree; the menu features a traditional English tea menu, including a variety of finger sandwiches, fruit and plain scones with house made preserves, Devonshire clotted cream, seasonal pastries with choux, chocolate, and winter fruit creations. (Vegan and gluten-free options are available). Festive Afternoon Tea is offered through January 9, 2022.

  • Guests at The Peninsula Chicago can celebrate Christmas Eve and Christmas Day (December 24-25, 2021) with a Christmas Eve prix-fixe dinner in The Lobby featuring Wagyu, Maine Lobster, Scallops and Peking Duck followed by a lush dessert buffet. A trio band will provide the entertainment and dinner is priced at $205 per person, with an option to add wine pairings for $65 per person. Or they can join for brunch in The Lobby on Christmas Day with an American four-course menu featuring à la carte options combined with buffet items served from a carving, seafood, cheese and charcuterie station and a decadent dessert buffet. A string quartet will provide the entertainment as well as a balloon artist and magician to entertain children. Brunch seatings (10:00 AM to 5:00PM) are priced at $275 per adult, $75 per child (five to 12 years).
  • Ring in 2022, Peninsula-style at The Lobby’s New Year’s Eve Gala (December 31, 2021), where a five-course prix-fixe dinner and dancing will be accompanied by a live band. The 21+ event is black tie optional and is priced at $205 per person with an additional $95 for wine pairings. Z Bar will also be ringing in 2022 with a ticketed soirée starting at 8:00 pm with an open bar, abundant passed hors d’oeuvres, DJ-ed entertainment and a Champagne toast at midnight. The party concludes at 1:00 am. Tickets for this 21+ event are $195 per person, excluding tax and gratuity. 

The Langham Chicago’s Holiday Afternoon Tea will return in partnership with Veuve Clicquot from November 17, 2021-January 9, 2022, where delicate pastries and savory petite sandwiches will be joined by Langham’s proprietary tea blends, seasonally-inspired treats and a special course from Veuve Clicquot.

© 2018 Galdones Photography
  • Travelle at The Langham will serve a Christmas Eve Entrée Special (priced at $82 per person) on December 24, 2021 from 5:00-10:00 PM; the menu will include a truffled chicken “pot pie” for two adorned with herb-roasted chicken, truffled confit thighs, black trumpets, and Caroline ruby sweet potatoes.
  • On December 25, 2021 Travelle will serve a Christmas Day Brunch (11:00AM – 3:00PM) with a variety of breakfast favorites, omelets made to order, artisanal cheese and cured meats, exquisite sushi and seafood options, and heavenly pastries. (The buffet is $195 per adult and $60 for children 5-12 years of age, and prepayment and reservations are required through the Travelle Tock.)
  • Or there is a six course Christmas Day Prix Fixe Dinner ($165 per adult) from 5:00-10:00 PM featuring a Royal Kaluga Caviar Amuse, Beet Root Panna Cotta Salad and Wild Mushroom Risotto appetizer, followed by a Roasted Prime Filet entrée and dessert service of Mont Blanc and Petit fours by Chef Nitin.
  • Ring in the New Year at Travelle at The Langham with a New Year’s Eve Prix Fixe Dinner on December 31, 2021 (5:00-10:00 PM) with a seven-course prix fixe menu featuring dishes including Nantucket Bay Scallop Ceviche, Hudson Valley Foie Gras appetizer, and Grilled Australian Wagyu NY Strip. To finish off a magnificent dining experience, guests can enjoy an indulgent dessert with Intermezzo featuring lemon with Grand Marnier and an extravagant Chocolate Experience with Manjari mousse, praline cremeux, and hazelnut ice cream. A splendid wine collection will also be available à la carte. Reservations must be made in advance through the Travelle Tock and prepayment is required at $190 per adult.

Private experiences with Santa, dinner packages and private events offered by Swissôtel Chicago for the 2021 holiday season include: 

  • Holiday Tradition Package: Stop by Santa’s Presidential Pad with up  to 15 guests to visit the man of the season and overindulge in unlimited Swiss hot cocoa, champagne and holiday treats including Candied Orange SnoBall Cookies, Reindeer Chow, Eggnog Truffles and more. The experience also includes cookie decorating, crafts with Make to Celebrate, face painting and letter writing, complete with a visit to Santa’s Post Office. $50 of  the total price will be donated to SOS Children’s Villages Illinois. Available to book every Saturday and Sunday for $600/hour from December 4 – December 19, 2021; 10:00 AM-5:00 PM.
  • Family Dinner Package: Gather with six or more loved ones for an over-the-top holiday dinner in  the Santa Suite, Duplex Suite, Vitality Suite or Chef’s Table Virtual Suite. Enjoy a 4-course  holiday-inspired menu by Chef Dan McGee, with menu items including Roast Chicken with red  cabbage, spätzle, raclette cheese, chicken jus, Pomegranate Braised Lamb Shanks with a  pomegranate bordelaise, Chocolate Peppermint Cake and more. Holiday crafts are available  upon request. Dinners are available to book daily beginning November 20-December 26, 2021 at $150 per adult and $50 per child.  
  • VIP Reception in Santa Suite: Whether it’s a  corporate holiday party or family reunion, the Santa Suite can fit up to 50 people for private  events beginning November 20-December 26, 2021. Work with the events team to curate an  experience with festive cocktails and a menu featuring Chilled Potato Soup & Caviar Shooter,  Smoked Duck Breast Marmalade, Curry Chicken Salad Sliders, Pecan & Roasted White Chocolate Tarts and more.  

Hotel Packages:

© 2018 Galdones Photography

A series of Yuletide specials this holiday season at The Langham Chicago (available November 19, 2021 – January, 2, 2022) include Oh Christmas Tree (including luxurious one-bedroom suite accommodations with a decorated Christmas tree in-room, deconstructed champagne cocktails inspired by the season; and bespoke cheese and charcuterie; rates beginning at $1,100) and Dive into the Season (including lavish guest room accommodations, $100 food and beverage credit for poolside snacks and beverages, two hours of exclusive access to Chuan Spa’s indoor pool and holiday-themed floats; rates begin at $825.

© 2018 Galdones Photography
  • Or splurge on A Signature Christmas in a 2,400 sq. ft. suite with floor-to-ceiling windows featuring panoramic views of Chicago, a four-course, in-residence dinner prepared by Executive Chef Damion Henry, in-suite dining entertainment, Club Lounge access and a custom-designed holiday tree set in the parlor. (Rates start at $13,525.)

At The Peninsula Chicago, holiday packages like the Holly Jolly Family Holiday Package and Merry and Bright Couple’s Holiday Package include such amenities as an in-room holiday tree or Menorah, holiday welcome amenity or bottle of wine/Champagne upon arrival, access to library of holiday themed movies, books and games for the kids or a $100 gift card to the nearby Neiman Marcus Michigan Avenue store, daily Peninsula breakfast and daily valet parking. Rates start at $1,250, packages available from November 26-December 31, 2021.

  • For six days, The Peninsula Chicago is offering special pricing for a Cyber sale commencing Thanksgiving Day (November 25, 2021) through Travel Tuesday (November 30, 2021) for 20% off rooms and suites on stays from December 1, 2021 – April 30, 2022. and special pricing on gift cards. The offers will only be available on the hotel’s website, or by calling the hotel directly.

For the eighth consecutive year, Swissôtel Chicagos Presidential Suite will be transformed into Santa’s home-away-from-the-Pole for the holiday season, welcoming Chicagoans and visitors alike. The Santa Suite offers sweeping views of the city, and is filled with 17 Christmas trees, festive decor, games and holiday craft kits for the kids, cookie decorating stations, “Letter to Santa” packs, and more. Book the Holiday Penthouse Hideaway (starting November 20 through December 26, 2021, from $1,500 per night). 

  • For a slightly more competitive price-point, consider a stay in an Elf Decorated Holiday Room featuring a Christmas tree and holiday room decor as well as a complimentary holiday amenity (Rates begin at $329 per night.)

Theatrical Performances:

A&A Ballet’s “The Art Deco Nutcracker” set in 1920s America and featuring Tchaikovsky’s beloved score, will play at the Athenaeum Theater on December 4, 2021. 

Charles Dickens’ A Christmas Carol, a must-see Chicago holiday tradition now in its fifth decade and enjoyed by nearly two million theatergoers, is back playing at Goodman’s Albert Theatre, from November 20 – December 31, 2021.

A Christmas Symphony Tour, a new Christmas tradition by the world’s biggest-selling soprano and GRAMMY® Award-nominated artist, Sarah Brightman, will play at the Auditorium Theatre on December 10, 2021.

“Home Alone” in Concert with the Chicago Symphony Orchestra, the beloved holiday favorite will return to the big screen at Symphony Center; John Williams’ delightful, Academy Award-nominated score will be performed by the Chicago Symphony Orchestra under the direction of Riccardi Muti, from November 26-28, 2021.

Leslie Odom, Jr.’s The Christmas Tour brings the GRAMMY®- and Tony®-Award Winning vocalist, songwriter, author and actor to Chicago for a one-night holiday season concert at the CIBC Theatre on December 4, 2021. 

Christopher Wheeldon’s reimagined classic The Nutcracker follows young Marie and the Nutcracker Prince on a Christmas Eve journey through the 1893 World’s Fair; this annual holiday tradition celebrating the magic of the season and the rich cultural heritage of Chicago returns to the Joffrey Ballet from December 4-26, 2021. 

“’Twas the Night Before…” by Cirque du Soleil i is the exhilarating spin on the beloved Christmas classic as only Cirque du Soleil can imagine a vibrant acrobatic spectacle about the joy of sharing and friendship at the The Chicago Theatre, playing from November 26-December 5, 2021

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