Your 2018 Chicago Holiday Bucket List

by matt on November 30, 2018

Winter is here, and the holidays are right around the corner. The lights, the people and the energy really makes me love living in the city…  However, I know that the month of December often slips away with all the office parties, holiday dinners, and the never-ending consumerism.

That’s why this month, I’m providing you with a bucket list of things to enhance your holiday cheer.  It’s not a contest and there’s no reward for doing them all, (although I would be seriously impressed!), just a simple list of great holiday activities for you and yours to enjoy.

In no particular order, I’ve listed some below and provided a detailed list on my website.

Channel Your Inner Kaner at Millenium Park Skating Rinks

The McCormick Tribune Ice Rink in Millennium Park lets visitors participate in this classic winter activity while taking in views of the Chicago skyline and the park’s iconic Cloud Gate, known lovingly as The Bean. The rink is open daily from mid-November to March and is free if you bring your own skates or you can rent a pair for a small fee. Additionally, skaters can weave through Maggie Daley Park nearby on the skating ribbon. Admission is also free if you bring your own skates or you can rent them for $12.

Give Back This Holiday at the Chicago Greater Food Depository

Volunteers play essential roles in distributing food to our network of pantries and programs. With help from 22,163 volunteers, nearly 70 million pounds of food were donated to hungry people last year. Grab some friends, family or just yourself and help to make a difference this holiday season.

See The Nutcracker at the Joffrey Ballet

Chicago’s Nutcracker is a must-see tradition boldly reimagined for a new generation.  This holiday masterpiece takes viewers on a journey to Chicago’s 1893 World’s Fair and not to be missed for young and old alike. Held in the iconic Auditorium Theatre and performed by the world-famous Joffrey Ballet, this should reserve a spot on your list for sure.

Ride the CTA Holiday Train or Bus (aka The Holiday Express)

The train began on the Blue Line in 1992 when a “Season’s Greetings from the CTA” sign was placed on the front of an out-of-service train used to deliver food to various charities. Today, the train 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.  Schedule available via the link.

Sip cocktails in an Igloo overlooking the city at The Godfrey

The Godfrey Hotel is offering shelter from the winter elements in style, with heated, see-through igloo domes atop their award-winning rooftop lounge, I|O Godfrey. There will be one large, centered igloo rooftop lounge that seats up to 10 guests, along with other smaller igloo lounges that seat up to six.  Reservations are suggested!

See Christmas Around the World and Holiday Lights at the MSI

Since 1942, the Museum of Science and Industry has decked its halls and exhibit rooms with holiday cheer as part of their Christmas Around the World event. This year more than 50 trees feature decorations inspired by cultures around the world and surround a 45-foot showpiece tree adorned with over 30,000 lights. As an added bonus, artificial snow falls in the museum’s rotunda every half hour.

Stroll the Zoo Lights at Lincoln Park Zoo

Celebrate the holidays with the animals at Lincoln Park Zoo during their annual ZooLights event. Brightly-lit exhibits are staged throughout the zoo and trees are draped in twinkling lights to enjoy as you stroll between the animal habitats. The lights stay on nightly until January 3 and admission to the zoo is free.

Lose Yourself at Navy Pier’s Winter Wonderfest

Holidays at Navy Pier offer an impressive array of holiday-themed activities during its annual Winter WonderFest. There’s a 170,000-square-foot ice skating rink, a 50-foot-high indoor Ferris wheel, along with 24 additional rides. If the activities don’t entice you, visit for the decor, which includes nearly 500 trees decorated with more than 25,000 ornaments. You have until January 10 to take it all in and general admission is $10 or $25 for activities.

Relive Your Childhood at Macy’s Great Tree

Dating back to 1907, it’s been a Chicago tradition to enjoy a holiday meal in Macy’s (formerly Marshall Field’s) seventh-floor Walnut Room adorned with the 45-foot-tall Great Tree.  No reservations are taken and expect to wait for a table, but there’s plenty to do around the store to occupy your time. Don’t miss the massive Tiffany Dome, which contains a mosaic of than 1.6 million glass pieces. The Great Tree provides plenty of photo opportunities as well with its 42 LED stars and countless additional lights and ornaments.

Keep a Loved One Warm at The Chicago Christkindlmarket

This German-inspired outdoor market features food, drinks, shopping and entertainment in Chicago’s Loop neighborhood. Tents pop up in Daley Plaza selling German glass ornaments, nutcrackers, bratwursts, strudel and mulled wine served in a souvenir mug shaped like a boot. Christkindlmarket is open daily between November 20 and Christmas Eve and admission is free.


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