After many years of saying, “We should take the kids to Chicago,” we’re doing it. We’re timing the kids’ first visit to Chicago to be during the holiday season, so in this particular Chicago bucket list, I’ve included holiday shows, lights displays, and special events, as well as a few dining wishes. So, here’s my Chicago Christmas bucket list, all the things I’d do in the Windy City if time and money weren’t a factor.
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Related post: Holiday Weekend In Chicago Itinerary
Catch a holiday show
There is an overwhelming assortment of live shows in Chicago between November and December. Narrowing down holiday show choices, you can find anything from traditional options like Joffrey Ballet’s “The Nutcracker” to more contemporary shows like “How The Grinch Stole Christmas.”
Shop the most famous Midwestern holiday market
Christkindlmarket is an open air holiday market in the heart of downtown Chicago. It’s modeled after German Christmas markets and looks completely charming.
While browsing vendors, I envision myself warming up with some Gluhwein. I’ve heard the Snow Balls (donuts) at Christkindlmarket are tasty and pair well with the Gluhwein, too.
The Magic of Christmas Tour includes a stop at Christkindlmarket, where they tell you what else you should sample while there!
Attend the biggest holiday celebration
I’m missing this parade this year, but since the Magnificent Mile Lights Festival is said to be to be the largest holiday celebration in the country, I’ve got to add it to my bucket list.
This annual event is held the weekend before Thanksgiving, and includes a popular parade.
Enjoy winter outdoor fun…indoors
Here’s another annual event that sounds like fun, especially for my little ones, but just isn’t timing out to coincide with my visit. Winter Wonderfest is an annual event at Navy Pier is held in December and features bounces houses, slide, carousel and all the typical outdoor things brought indoors.
I bet we’ll still go to Navy Pier this November to ride the ferris wheel and maybe take a walking food tour.
See trees in a different light
OK, technically this is outside of the city, but I hear “Illumination: Tree Lights at The Morton Arboretum” is worth the drive. This annual holiday event at Morton Arboretum features an illuminated path of trees programmed with lights, video and audio.
See the city from way up high
Chicago will be my kids’ first encounter with legit skyscrapers. I can’t wait to take them to one of the tourist spots to get a bird’s-eye view of the city.
If we’re feeling daring, there’s the 360 Chicago and viewing the city from Hancock Tower’s Observation Deck or The Ledge experience at the Skydeck at Willis Tower.
Holiday fun at Art Institute of Chicago
Wish we were in Chicago in December so we could attend the annual Holiday Treasure Hunt and Tea Party at Art Institute of Chicago. We’re also missing the annual Hanging the Wreaths on the Lions there (it’s earlier in November).
I’m OK going to the museum without the additional holiday event crowds, though. I’ve never been there, and it’s been named the No. 1 museum in the world so I’d better fix that.
Related post: Tips For Taking Kids To The 3 Biggest Chicago Museums
Holiday dining to remember
While researching dinging options, some restaurants in Chicago stood out for making dining between Thanksgiving and Christmas a special occasion, if only for unique decorations.
First on the list is The Walnut Room at Macy’s, which was the first restaurant in a department store ever opening in 1905. Word is, at Christmas time, there is a 45-foot-tall tree, which sparkles with 3,000 ornaments and 6,000 LED lights, in the dining room.
A bit more casual is Butch McGuire’s, a bar that goes all out for Christmas with thousands of lights and a double-decker model train. The Local Tourist says children are welcome for lunch and brunch.
Dine like a spy
OK, this is not holiday-related, but my kids are at an age when a visit to SafeHouse Chicago sounds so perfect, it has to happen when we’re there.
SafeHouse is often described as a spy-themed bar and club, but if you go during the day, you can dine at a restaurant that sounds surprisingly family-friendly. My kids’ imaginations will have a field day at this place.
How could I not when the stores will be decorated for Christmas shoppers? I hear Macy’s has a good display each year.
Ice skate outdoors
One of my friends who lived in Chicago for years recommended two different places to ice skate: McCormick Tribune Ice Rink in Millennium Park, with its iconic skyline views, and Skating Ribbon at Maggie Daly Park, which breaks the mold of the typical oval ice rink.
Rumor has it there may be a special Skate With Santa event. I’m crossing my fingers for an unusually warm winter day so we can visit.
Be in Chocolate Heaven
What’s the best drink for the holidays? Hot chocolate. Xoco has a churros and a spicy hot chocolate that are calling to me, but there are so many places to try, from Mindy’s Bakery to the over-the-top “hotter chocolate” creations at BomboBar.
Why stop with hot chocolate? Chocolate at the Pen is a chocolate bar at the Peninsula Hotel held every Friday and Saturday night and it is the stuff I’ve been dreaming about.
Also, word is there’s a Nutella bar at Eataly (in addition to a ton of Italian food that’s rumored to be stunningly good).
Related post: Done with winter? Check out my Chicago summer bucket list!
Lights, Santa & animals
Winter isn’t typically the most popular time to visit a zoo, but I bet things get a little busy at ZooLights at Lincoln Park Zoo. It’s been running for 24 years.
This evening event is FREE (just like the zoo itself), and I hear Santa waits for kids at the Kovler Lion House. My question – how many animals do we actually see at ZooLights?
Stroll the indoor gardens
Conservatories and indoor gardens are my favorite in the winter – they’re like a little oasis in the cold. Two places in Chicago have holiday displays to visit. Wonderland Express at Chicago Botanic Gardens features miniature trains, indoor snow and beautiful gardens from mid-November to early January.
Garfield Conservatory has its annual Holiday Show from mid-November to early January, too, and this one has a bonus of being FREE.
Golden ticket to ride
How special is this? There’s The Polar Express Train Ride in Chicago. It’s an Amtrack event from Chicago Union Station through the holiday season.
Best part? You can wear PJs.
Making use of reciprocal membership perks
I’ve written about reciprocal membership perks, which you’ll want to read here. My Omaha Children’s Museum membership gets us FREE admission into quite a few Chicago museums. Two are on my list to visit: The Field Museum and the Museum of Science + Technology.
One reason I want to go to Museum of Science + Technology this particular time of year is that there’s the annual display called “Christmas Around the World and Holidays of Light.”
See the gaudy Chicago Christmas lights
Time Out called the Christmas lights in Lincolnwood Towers as “straight-up Griswald sh**.”
Getting “Snowed Inn”
I’ve been looking into Chicago hotels that cater to families and Loews Chicago might win for my favorite holiday/winter package: Each year, they have a “Snowed Inn” themed package that includes hot cocoa & cookies, an in-room movie, and a tent set up with a little kids campfire – PLUS, for the parents, valet parking.
Read reviews and book a stay through TripAdviser!
Santa goes high-tech
Santa HQ, presented by HGTV, at Fashion Outlets of Chicago sounds like a high tech experience that elevates a simple visit to see Santa. It involves iPads and apps and some nifty machines that calculates how naughty or nice you’ve been.
Maybe seeing a beluga isn’t exactly holiday-related but no Chicago bucket list is complete without mentioning Shedd Aquarium. When I read about some of their animal encounters, like one with a beluga, I knew I needed to add it to my bucket list.
Alas, the age requirement is 12 and older, so it would just be me and the beluga, my kids would just have to watch. 🙂 They can, however, join me for a penguin encounter. Fun!
Check back later this year for details on our trip and see how many of these items we checked off!
Friday 21st of December 2018
Christmas in Chicago is magical.
Monday 22nd of October 2018
wow chicago christmas pictures... Thanks for the information
Friday 5th of October 2018
I really want to go to the Christmas market in Chicago! I've been close to going so many times but then things have come up so I haven't gone! I land back in Chicago after a trip on Dec 3rd so I wonder if my other half would mind if we took a sneaky detour into the city haha
Saturday 6th of October 2018
Do it! Get some snacks for the drive home.