Winter break is a significant milestone in the school year. It marks the end of the first semester and the start of the second. Additionally, people celebrate their favorite holidays and get to spend time with their family and friends. But, the real question is what to do with all the extra time?
Look no further! Here are five things to do in the Chicago area over winter break.
1. Take a trip to the German-Style Christkindlmarket
The Christkindlmarket is a Chicagoland staple. There are three locations, one being in Aurora, the next being in Wrigleyville, and the most popular being in the Daley Plaza in the heart of downtown Chicago.

Aurora’s location is located in RiverEdge Park, which is a little over an hour drive from Palatine. Wrigleyville’s location is located in Gallagher Way on the North side of Chicago complete with an up close view of Wrigley Field. Chicago’s main location is located in the Daley Plaza, just a 12 minute walk away from the Cloud Gate, better known as “The Bean.”
Most importantly, an array of food, drinks, ornaments, Christmas decor, trinkets and Christmas gifts are available for purchase at all three locations to give it that 16th century German market feel.
Some of the most common food and beverage items include gourmet stuffed pretzels, potato pancakes, strudels, raclette cheese sandwiches, Bob’s Belgian hot chocolate, schnitzel and hot roasted nuts.
Additionally, every year the Chriskindlmarket creates a new mug design that is available to purchase. A lot of people buy a mug each year they attend the market and grow their collection year by year. This year’s mug for 2025 is shaped like a heart with a striking red exterior and handle.
Whether you are looking for the perfect christmas gift for someone, or just want to enjoy the holiday cheer while sipping on hot chocolate, the Chriskindlemarket is the perfect place to do both.
2. Go ice skating at the Maggie Daley Park Ice Skating Ribbon.
Ice skating is one of the most popular activities that people partake in each year, especially around the holidays.
One of the rinks in Chicago is at the Maggie Daley Park and it’s in the shape of a giant ribbon. There are multiple skating two hour skating sessions each day, starting as early as 8 AM and ending as late as 10 PM.
Renting skates costs $17-$21 if purchased online or costs $19-$23 if someone buys them in person.
Skating spots are very limited though so be sure to make a reservation online for a specific skating session to make sure a spot is secured.
Ice skating is the perfect activity for families or for groups of friends looking for a fun night out.
3. Enjoy a festive meal at the 118 year old Walnut Room restaurant
The Walnut Room is located inside of Macy’s, or what used to be the Marshall Field’s department store. Every year a giant tree is set up and decorated completely differently than the year before. This year the tree is mainly decorated with colors of blue, green and gold, paying homage to the iconic Marshall Field’s green theme. The tree is displayed from Nov 1 through Jan 11.
Reservations are a hot commodity though and go extremely quickly. They were originally available to book starting all the way back on Sept 25 at 9 AM. It’s always worth a shot to check availability on the day of though!
Additionally, The Walnut Room has its very own holiday menu. Some of the most common dishes

include, cider glazed turkey, cranberry citrus chicken salad sandwich, braised short rib, asiago crusted chicken, Field’s special salad and of course, the 135 year old Mrs. Hering’s original chicken pot pie. There are even an array of holiday desserts to choose from including mint chocolate cream pie, Field’s double chocolate fudge cake, carrot cake, holiday yule log and mint chocolate cheesecake.
Also, The Fairy Princess will be visiting The Walnut Room every Saturday to bring even more festive cheer.
Overall, The Walnut Room is the perfect place to enjoy a delicious breakfast, lunch, or dinner surrounded by holiday magic.
4. Visit Cantigny Park to partake in their Christmas at Cantigny events
Cantigny Park is located in Wheaton and has everything from a tank park and historic museum, to luscious gardens. They have a wide variety of events year round but during the holiday season is when they shine the brightest.
First off, Christmas at Cantigny has light shows to see. One of them is even Wicked and The Wizard of Oz themed!
Admission to the light show at Cantigny can range anywhere from $12-$25 depending on age and day of the week. Parking is free if booked in advance.
Additionally, Cantigny has its very own ice rink! Admission to the rink is $7 and skates are available to rent for only $3.
The park even has Cocoa Cabanas available to reserve starting at $125 and holds up to 10 people. It includes food, full bar service, server attendant on site and a whole two hours of use. Each cabana even has a fire table and heated seating area.
Also, a Colonel Christmas Tour is available to embark on. The cost is $75 and includes light show admission, early admission and a drink. A tour of the historic McCormick house is provided before the doors open to the public.
Overall, Cantigny park has a multitude of activities to keep visitors entertained during the holiday season.
5. Take a trip to the Home Alone house and Home Alone pop-up bar
The nostalgic Home Alone house is located in Winnetka, about a 35 minute drive from Palatine. This was the real house used when filming the iconic 1990 Christmas movie.
Feel free to snap a quick selfie or photo on the sidewalk in front of the house. Unfortunately, it is a private residence so the inside is not open for guests, but the sidewalk is fair game.
After getting pictures, there is a Home Alone pop-up bar just a 3 minute drive away. The cafe’s name is “Towne & Oak” and is open for both breakfast and lunch. It is decked out with Home Alone decorations and movie references.
Some notable stand outs from their menu include their honey crisp apple salad, smashed avocado tartine and their chicken taco bowl.
A Home Alone themed day just a short drive away from Palatine is the perfect thing to do during the Christmas season!
