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The Things To Do This Winter & Holiday Season in Chicago

The Things To Do This Winter & Holiday Season in Chicago

There are two different kinds of people: The one’s that have the holiday music and decor cued up for Nov. 1 and there are those that wait til after the Thanksgiving turkey has digested before even hanging up a light, cueing the Mariah Carey Christmas music playlist or putting up their tree. Regardless of where you stand, its always a good idea to have a list of things to do come holiday season time. Now that Mickey and Minnie have officially lit the Magnificent Mile lights, its time to get to the seasons best offerings. Whether you have family and friends visiting from out of town or looking to get into things with friends or solo this season, you will find yuletide and joy in our curated list below.


photo credit: Eric James Walsh

To Do: Chicago Christkindlemarket

Is there a true list of anything holiday/winter related in Chicago if the Christkindlemarket isn’t involved?! Chicago’s favorite outdoor holiday tradition since 1996, inspired by Nuremberg Germany’s Christkindlmarkt-or-Christkindlesmarkt Christmas market, is back for another year and in addition to the well known Daley Plaza location, you can also shop/explore the Wrigleyville and Milwaukee markets too. There’s a special three pack of the 2019 mugs of all three locations available for purchase.

Dates: November 15 through Dec 24 2019 | Sunday – Thursday 11am – 8 pm; Friday – Saturday 11 am – 9 pm
Location: Daley Plaza – 50 W Washington
Cost: Free to attend but bring money for vendor purchases | Visit Website

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To Do: Ice Skating at McCormick Tribune Ice Rink at Millennium Park

Take a spin on the ice during the 18th season of this Chicago winter tradition of ice skating at McCormick Tribune Ice Rink at Millennium Park presented by Hilton. Guests staying any of Hilton’s 17 hotel brands can claim two pairs of complimentary ice skates per room reservation. There are definitely plenty of picture taking opportunties between the rink and the nearby Cloudgate aka The Bean. For the Johnny Weir’s in the making, the Winter Workouts program will offer free skating lessons for all ages and skill levels, one hour before the rink opens on select days and time. For those looking to make a day of it, cap it off with some dinner at the Gage or drinks and bites at Cindy’s at the Chicago Athletic Association Hotel.

Dates: November 15, 2019—March 8, 2020 (weather permitting)
Location: Michigan Ave. btwn. Washington & Madison Streets
Cost: Free admission, skate rental (M-Thur: $13) (Fri-Sun+Holidays: $15); Coin-operated locker rentals (4 quarters) | Visit Website

To Do: Christmas Around the World and Holidays of Light at Museum of Science and Industry Chicago

The Museum of Science and Industry Chicago’s beloved annual celebration features a four-story, floor-to-dome 45-foot-tall Grand Tree with more than 45,000 lights and ornaments surrounded by a forest of more than 50 trees and displays decorated by volunteers to represent the holiday traditions from cultures around the globe. On the weekends, guests can also enjoy live holiday performances. It’s the one-of-a-kind experience that brings a whole world of holiday joy under one roof.  This annual tradition began in 1942 with a single tree, newly decorated every day for 12 days to represent the countries fighting alongside America during World War II.

Dates: open through January 6, 2019
Location: Museum of Science and Industry | 5700 S Lake Shore Drive Chicago 60637
Cost: included in Museum Entry; Members – FREE; Adult – $21.95 ($19.95 online) | Visit Website

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To Do: Allstate CTA Holiday Train & Holiday Bus

As much as riding the CTA might be a dreary experience most times, what with crowded train cars during rush hour, the sometimes scentiful eu de peepee and what not, the bright lining during the holiday season is the CTA Holiday Train. The Allstate CTA Holiday Train is back for another holiday season with schedules based on the train lines and this year back by popular demand will be the Allstate CTA Elves’ Workshop Train accompanying the holiday train, a six-car train of magic and memories. Complementing these two festive trains is the Allstate CTA Holiday Bus, which brings the same holiday spirit and joy to bus riders as it travels throughout Chicago’s neighborhoods featuring multi-colored lights, holiday-themed seating, candy-cane striping, artwork created by students from Perkins Bass Elementary School. The holiday train, which began on the Blue Line in 1992, serves two very important purposes: to deliver joy and the holiday spirit to thousands of riders and also to deliver food baskets to various charitable agencies throughout the city. You can use the holiday tracker to check on the trains through the season.

Dates: November 29 — December 23
Location: Green, Orange, Pink, Blue, Purple, Brown, Yellow and Red Line
Cost: Cost of transit fare | Visit Website

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To Do: Lincoln Park Zoo Zoo Lights

Come celebrate 25 years of ZooLights at Lincoln Park Zoo this holiday season with a one-of-a-kind, festive holiday experience that offers free, merry, family-oriented celebration of joy right in the heart of the city of Chicago. There’s something for all ages including photos with Santa through December 23 and breakfast with Santa on December 15. For those readers that are kiddie free, there’s BrewLights (December 12) and Adult Night Out: Holidaze (December 5). Members of Lincoln Park Zoo and their guests get to enjoy exclusive access to a preview of ZooLights on November 22 from 4:30–9 p.m. before it opens to the public on November 29 on 4:25 p.m

Dates: November 29-January 5 | 4:30–9 p.m.
Location: Lincoln Park Zoo | 2001 N Clark Street, Chicago 60614
Cost: Admission to zoo is free though there are ticketed experiences | Visit Website

Chicago Botanic Garden

To Do: Lightscape Holiday Lights Trail @ Chicago Botanic Garden

Direct from London, Lightscape is making its U.S. debut at the Chicago Botanic Garden with new magic just in time for the holidays. Strolling along a mile-long path, the night comes alive with color, imagination, and sounds from a playful choir of singing trees to a spectacular waterfall of light. Lightscape holiday lights at the Chicago Botanic Garden is an enchanting, after-dark, illuminated trail inspired by and created just for the Garden. Guests will find themselves in the center of it all — stepping inside a sparkling tunnel, walking among immersive ribbons of light, enjoying a stunning festive finale and toasting marshmallows over a fire. The Chicago Botanic Garden is producing Lightscape in partnership with Sony Music, which amazed more than one million people in 2018 with similar shows in multiple locations across the U.K.

Dates: Friday, November 22, through Sunday, January 5 (4:30 – 10 p.m.)
Location: Chicago Botanic Garden | 1000 Lake Cook Rd, Glencoe 60022
Varies Adult between $17-$25 |
Visit Website

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To Do: Chicago Helicopter Holiday Lights Experience

Take in the sights and holiday magnificence of Chicago from a few thousand feet above. The memorable one of a kind holiday lights experience provides stunning views of Chicago’s iconic sites including the Willis Tower, Millennium Park, and the Lincoln Park Zoo Lights all lit up for the holidays from the comfort of our warm and cozy helicopters. Your flight will cover 25+ miles of Chicago’s Holiday themed skyline in 12-15 minutes. You can take advantage of their “Black Friday” special and get a 30% saving per passenger.

Location: Downtown heliport 2420 S Halsted Street, Chicago
Cost: $125 – $750 | Visit Website

Photo credit: via Hyde Park Chicago Holly-Day

To Do: Hyde Park Chicago Holly-Day 2019

This is a very family friendly geared event which we don’t cover much on but we love Hyde Park and any chance to watch a Free movie(helloooo Frozen 2) and head down to Harper Court and take in some comforting and delicious food at Virtue, is a good time. For those looking to attend Holly-Day, activities such as FREE screening of Frozen 2 at Harper Theater, picture with Soul Santa and Mrs. Claus, Ice carving demonstration, Holiday Crafts & Activities, Dance Performances PLUS hanging out with Buddy the Elf and two live reindeers.

Dates: Saturday, December 7 starting 10am.

Location: Harper Court | 5235 S. Harper Court, Chicago
Cost: Reservation required for Frozen Movie screening | Visit Website

Nick Ulivieri Photography for Navy Pier

To Do: Navy Pier’s Winter Wonderfest

Packed with indoor fun, the 19th annual Fifth Third Bank Winter WonderFest at Navy Pier is a delightful holiday time tradition featuring 170,000 square feet of attractions, including rides, giant slides, indoor ice skating, and holiday decor that is sure to get you into the holiday spirit! This is mostly taking place at Navy Pier’s Festival Hall so be prepared to walk what feels like 50billion miles before you reach your beautiful destination. Upon entry to Fifth Third Bank Winter WonderFest, guests will be greeted by abundant winter decorations and a twinkling forest of nearly 500 trees decorated with 25,000 ornaments hung on glittering wire. Dozens of classic rides and attractions will adorn the Pier’s Festival Hall under shimmering white lights and above a wintery blue carpet, including the Xfinity Ice Skating Rink, Polar Extreme Obstacle Course, Cliff Hanger, Polar Ice Peaks Climbing Walls, Winter WonderWhirl, Kringle Carousel, an all-new holiday market featuring meet-and-greet opportunities with Santa and Mrs. Claus on select dates and more. It could feel like a family (read: kiddie zone) affair but its for all ages and besides you can head up to Offshore for drinks after getting pics for the ‘gram.

For the young professionals and kiddie free, the Navy Pier Associate Board will host Cheer at the Pier on Thursday, December 5 from 5 – 9 p.m. as an exclusive pre-opening celebration of Fifth Third Bank Winter WonderFest. Open bar for 21+ and access to all rides and activities at Winter WonderFest.

Dates: December 6, 2019 — January 12, 2020
Location: Navy Pier |
Cost: Varies | Visit Website

Photo credit: Cheryl Mann for Joffrey Ballet

To Do: The Nutcracker at the Joffrey Ballet

Tony Award-winning 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 off a whirlwind journey of romance and adventure through a dreamlike World’s Fair.
The reimagined Nutcracker, which debuted in Chicago in 2016 is back for the holiday season. New this year is an additional “Worker Girl” role who appears in Act I, following the prologue, during the ballet’s iconic party scene. The Nutcracker runs approximately 2 hours including one 20-minute intermission. Guests can also enhance their Nutcracker experience by attending a Nutcracker Afternoon Tea the day of your performance at the JW Marriott Chicago.

Dates: November 30-December 29

Location: Auditorium Theatre | 50 East Ida B. Wells Drive (formerly Congress Pkwy), 60605
Cost: Varies | Visit Website

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To Do: Illumination: Tree Lights at Morton Arboretum

In this unparalleled spectacle of color, light, and sound, you will be awed and delighted to see returning favorites and surprising new sights, including Tree Fascination–a brilliant digital projection of immersive color and pattern on a grove of Eastern white and Scots pine trees. Illumination will highlight the many gifts of trees: natural beauty, increased feelings of peace and calm, homes for wildlife, and the air we breathe. This year’s event will debut a new route with a more spacious pathway.

See Also

See trees in a different light at Illumination: Tree Lights at The Morton Arboretum. Be surrounded by color as you walk a one-mile paved path amid interactive lighting effects that highlight the beauty of trees in winter. Enjoy seasonal music, marvel at ever-changing, captivating lighting designs, and warm up by a crackling fire with a cozy drink or roast marshmallows for s’mores. Note to guests: The exhibition is not fully accessible to visitors with limited mobility. Illumination trail is a one-mile paved walking path that includes a large incline approximately halfway through the exhibition (Ornament Hill), and several smaller inclines and declines.

Dates: November 23, 2019–January 5, 2020 (closed select days)
Location: 4100 Illinois Route
Cost: Member (Adult: $13; Child: $7); Nonmember (Adult: $18; Child: $12) | Visit Website

Photo credit: Art Institute Chicago

To Do:Wreathing of the Lions @ Art Institute of Chicago

Its beginning to look a lot like Christmas when the lights on the Mag Mile goes up and the Guardian Lions in front of the Michigan Avenue entrance of the Art Institute of Chicago are decked out in their holiday wreaths. Come join merrymakers on the Michigan Avenue steps as the Art Institute reveals the beloved lions in their festive wreathes at the 28th annual Wreathing of the Lions at the Art Institute of Chicago. Enjoy special performances by Chicago Gay Men’s Chorus and complimentary hot chocolate while you welcome the holiday season. After the les than 1 hour long ceremony, head inside to check out the “Andy Warhol — From A to B and Back Again” exhibition currently n view til January or lunch at Terzo Piano, a beautiful hidden gem in the city.

Dates: Nov 29 | 10:00–10:30
Location: Art Institute Chicago | 111 S Michigan Avenue, Chicago 60603
Cost: Free to attend wreathing; Museum entry cost varies | Visit Website

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To Do: Afternoon Holiday Tea at the Langham Hotel Chicago

This is money well spent if we dare say so. The Langham Hotel’s classic heritage signature afternoon tea with Wedgwood will transport you back to the original hotel, The Langham, London, where the tradition was born. Surrounded by the Langham Hotel Chicago’s stunning decor, soaring ceiling and marvelous city view, guests will be treated to proprietary Langham teas, and an array of sweet and savory bites served with traditional displays and flourish, accompanied by live music Friday through Sunday.

Dates: November 16, 2019 – January 21, 2020 | Mon – Fri: 1:00pm – 5:00pm; Sat – Sun: 11:00am – 5:00pm
Location: 330 North Wabash Avenue, Chicago 60611
Cost: $80 per person; $50 per child age 5 – 12 | View Website

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To Do: Frosty’s A Christmas Bar

Chicago’s Adult Holiday Experience pop-up ultimate Christmas bar! 4 bars, 3 levels, 2 dancefloors. The Frosty’s Christmas Bar is heavy on the holiday nostalgia with life size toy soldiers, ribbons & wreaths, garlands, and a holiday soundtrack spinning until 4am.

Dates: November 27, 2019 — January 5, 2020
Location: 809 W Evergreen Ave, Chicago 60622
Cost: Individual and Large party tickets available | Visit website

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To Do: Maggie Daley Park Skating Ribbon

With the City’s skyline as a backdrop, take in the holiday and winter season fun of outdoor skating at Maggie Daley Park’s skating ribbon. You can join in two themed holiday events: Ugly Sweater skate on Saturday December 7 and Skate with Santa on December 14 from 10am-12pm.
Dates: November 15–
Location: 337 E. Randolph Street Chicago 60601
Cost: Admission is FREE; skate rental (M-Thur $13; Fri-Sun $15); Locker rental $3; Fast Pass also available | Visit Website

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