Throughout my first semester as a college student, I’ve been looking forward to visiting my hometown for the holidays. I live 30 minutes away from Chicago, and it’s by far the best place to be for the winter. Midwesterners have a reputation for being a bit cold and uninviting, but over the holidays, everyone you pass is smiling and warm despite the windy and frigid temperatures.
As I prepared to come back for winter break, I went over the staple Chicago holiday festivities in my head. Of course, I remembered the classic bucket list places I knew my family and I had to visit, but I researched quite a bit to find new things to explore, as well. From holiday displays to pop-ups to shows in the theatre, there are plenty of things to do for any visitor or native in the Windy City this winter season!
- Light Shows and Holiday Displays
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There are so many options for seeing holiday displays or festive lights in Chicago, but a few in particular stand out from the rest.
Of course, there’s the stunning Chicago Christmas tree in Millenium Park, where many wedding proposals take place throughout the season, and while you’re there, you can also see the (now renovated) Bean!
If you’re closer to Navy Pier, they’re having a Light Up the Lake event until Jan. 5 this winter. The event has a ton of activities like a large outdoor light display, fire pits to warm up at, and festive markets, among many other specialties.
My personal favorite tradition is going to Macy’s Holiday Windows, where the storefront windows collectively tell a wintertime tale as you walk along the building. Last year, the location wasn’t too busy and was a good alternative to the busy crowds you’ll find in the city’s hottest spots during the holidays. It also helps that it’s a story told through many windows, so the crowds get spread out across the display.
If you’re looking for a spot to warm up after looking at the window display, Macy’s has you covered. You can go inside and view the Great Tree before getting a dinner reservation at the Walnut Room. The Macy’s experience, in my opinion, is the most well-rounded option for a night out if you want to see a holiday display.
In addition to these displays, the Chicago Transit Authority (CTA) Holiday Train is in town, Lincoln Park Zoo is hosting a light display, and there’s the iconic Chicago Botanic Garden Lightscape illuminated trail. Even Maggie Daley’s Park is having a beautiful light showcase this holiday season!
- Ice Skating
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There are two top options for ice skating in the city, but Maggie Daley’s ice-skating ribbon is my top choice. The park has an ice-skating rink in a unique ribbon shape, allowing you to see the skyscrapers and beautiful views. I went last year with my mom and boyfriend, and we had such a great time!
One thing to note is that there are some elevation changes along the course, which can be pretty tiring. Each loop takes a decent amount of effort and time. so Keep this in mind when booking your time slots since you might not need a lot of time to feel satisfied with your skating experience.
A second option is the Millennium Park Ice Rink. This flat and classically shaped rink offers stunning views of the city and has a difficulty level that any skater can handle. The rink is nestled right below The Bean, where on one side, you can see this iconic Chicago landmark, and on the other, you can view skyscrapers and notable buildings.
- Holiday Shows
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Another year-long activity that feels extra special during the wintertime is seeing a show in the Windy City. The Chicago Theatre has shows, plays, musicals, and even stand-up comedies.
If you’re in the mood for a holiday-themed show, there are many offerings like A Christmas Carol, The Nutcracker, and White Christmas. My best friend’s family does a girl’s night out to see The Nutcracker every holiday season. The Chicago Theatre is truly a timeless experience for the winter!
- Museums
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One option that can be affordable and a great time is visiting the museums Chicago has to offer. The Shedd Aquarium has countless exhibits, and the penguin talks are a cute way to get into the holiday mood.
The Art Institute is hosting a “Home for the Holidays” event and even added wreaths to the lion statues in front of their entrance. You can take a look at the free museum day offerings to try and snag tickets to see these festivities for free!
- Pop-Ups
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Pop-ups are an activity that can be geared towards family or for an older audience. The most notable pop-up in Chicago is the Christkindlmarket. You can purchase their collectible mugs, some German food, or fun holiday knick-knacks. Just keep in mind that this attraction is a popular stop for many, so plan accordingly. There are two locations, and typically, the Wrigleyville location is calmer.
A special part of Chicago is the pop-up bars that appear during the holidays. What revealed these hidden holiday gems to me was a TikTok video of the Noche Buena at Moe’s Cantina in Wrigleyville. They’re a Latino holiday pop-up bar with the most stunning decorations.
You can find many types of these pop-ups if you start searching. If you’re looking for a Hunnukah-themed place, 8 Crazy Nights is for you. Another good spot is Jojo’s Shake Bar’s Winter Wonderland pop-up, which has non-alcoholic shakes if you’re looking for something everyone in the family can enjoy.
Rudolph’s Rooftop is exactly what it sounds like: a rooftop bar with cityscapes as the backdrop. Luckily, they have heated and see-through igloos, as well as tables inside to avoid the chilly weather. There are countless options for a nightcap or non-alcoholic treat before you head out of the city.
Overall, as I planned what I wanted to do over my winter break, I found a considerable amount of cool options for festivities this season! Some of these are classics that I’ve done every year, but there are many new ideas for holiday fun. I hope this compilation can help with planning an eventful and well-rounded trip to Chicago during the holidays.
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