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Holiday Activities In Chicago

It’s that time again! The holidays in Chicago are truly magical. There are so many things to do to celebrate the season and keep the spirit alive. Below is a list of all my favorite Chicago holiday activities you can do with friends or family over the next several weeks.

Head over to Gallagher Way. They just opened their Christkindl Market where you can shop unique gifts from all over the world and sip on some hot spiced wine. They also have Winterland which features ice skating every day of the week and you might even get a photo with Santa. There are some great restaurants nearby to grab a bite to eat too!

Next to Gallagher Way is Hotel Zachary. They host an upscale Breakfast with Santa every year that is what kid dreams are made of. The brunch is available on Saturdays and Sundays beginning November 27 through December 19, from 8 a.m. – 11 a.m. Adults for $50 per person and children 4 to 12 years are $20.

Need a little holiday magic? Book a ride on the Polar Express. We’ve been a few times and heading back this year and can’t wait. It truly is a magical experience.

If you want to explore Christmas and holiday traditions from all around the world, I highly recommend the Christmas Around The World and The Holidays of Light Exhibit at the Museum of Science and Industry. This tradition started in 1942 and each year the exhibit gets even better. It’s a must-see of the season. The exhibit runs through January 6th.

Seeing The Joffrey Ballet’s rendition of The Nutcracker is also a favorite holiday tradition in my family. From their website: The Joffrey’s beloved version of The Nutcracker takes inspiration from Chicago’s 1893 World’s Fair, one of the city’s great historical attractions of the late 19th century. The performances start on December 4 and run through December 26th.

Need a fun activity for the whole family? Grab tickets for the Light Up The Lake experience at Navy Pier. This is a new event this year and I can’t wait to check it out. Years past we would go to the Winder Wonder Fest and loved it so I know this will be a great experience too. From Navy Pier’s website: The indoor, temperature-controlled experience features a sprawling light garden of large-scale sculptures comprising more than 600,000 twinkling lights; an Alpine ice rink; authentic holiday beer garden; kiddie train rides; Santa’s Merry Main Street and gift market; and other family-friendly and date-night activities.

Light Up the Lake runs from Nov. 26 through Jan. 2. Tickets start at just $15.00, including a ride on the iconic Centennial Wheel, offering inspiring views of the city all decked out for the holidays.

Amaze Light Festival in Rosemont just opened at Impact Field and features millions of twinkle lights for an immersive experience. You can visit seven different “worlds”, visit Santa’s workshop, take a ride on Thrill Hill, or loop around on the Arctic Train. We just went this weekend and it is a must-visit!

If you’re looking for an inexpensive activity? Grab some friends or the family and head to a Christmas-themed bar! I always say you haven’t lived until you’ve been to a Christmas bar! Santa Baby and Rudoph Bar are my favorites. They are family-friendly if you go before 9 pm and the kids will love it. If you want some holiday fun with a view, book an Igloo at London House Chicago.

Don’t worry, I have some free things to do too! You can head to the Zoo Lights at Lincoln Park Zoo (Free Admission on Monday/Tuesday) or take a quick drive up to the North Shore to see the famous house in the holiday movie classic, Home Alone.

Lastly, I’m going to share some Santa sightings! If you want to get some pictures with the kiddos and Santa, here are some of our favorite locations.

900 North Shops Santa has now arrived at 900 North Michigan Avenue on Level 3 on Saturday, November 19 – Saturday, December 24.

Skydeck Chicago at (Sears!) Willis Tower is hosting Santa at Skydeck! This event is held in the lower-level museum portion of Skydeck Chicago in a full-scale ‘L’ train replica where Santa will be riding and be available for photos from December 18–24, from 12 p.m. – 4 p.m.

Macy’s Santaland This is our favorite Santa. We’ve been going to Santaland since my kids were newborns. The whole experience is something we look forward to each year.

Museum Of Illusions now has Santa Sundays at the museum every Sunday morning between Thanksgiving and Christmas. From their website: It’s time to get silly with Santa! Santa will be strolling through the Museum of Illusions every Sunday morning between Thanksgiving and Christmas from 9am until 12pm. Now’s your chance to size up Santa in the Ames Room and get dizzy with him in the Vortex Tunnel. Children will be thrilled to share their Christmas wishes with the big guy and parents will get photo ops galore. All children attending Santa Sundays will receive a special holiday treat at the end of their visit. Tickets are $25 and must be purchased in advance at

Happy Holidays, friends! Here’s to a fun season.

About Me


Holly Rust

Chicago Boy Mom – Author – Side-Gigging CEO On The Go. Social Media Maven. Eternal optimist. Lover of travel, food, style & beauty. Follow my random thoughts, favorite things and life shenanigans here. Be sure to follow me on social, too! Links below.

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