Chicago at Christmas With Kids: The Perfect 3-Day Holiday Itinerary
If you want a city that really goes all in on Christmas, Chicago is such a fun and easy one to do with kids. We visited during the holiday season and honestly loved how much there was to do that felt festive without making the entire trip revolve around Christmas events. You can ice skate downtown, wander through a German Christmas market, see a holiday show, shop along the Magnificent Mile, eat deep-dish pizza and then easily go inside somewhere fun when everyone needs to warm up. And trust me… we needed those warm-up breaks.
The week we visited happened to be unusually cold, so we learned very quickly that the secret to doing Chicago in winter with kids is not planning to be outside all day. We alternated outdoor sightseeing with indoor stops like the Starbucks Reserve Roastery, Museum of Ice Cream, restaurants and our hotel pool, and it made the trip SO much more enjoyable.
You could easily spend longer here, but I think 3 full days is the perfect amount of time for a long holiday weekend. So if you’re planning a trip to Chicago around Christmas, here is exactly how I would do it with kids.
First, where we stayed at the InterContinental Chicago Magnificent Mile and it ended up being such a great choice with kids, especially in the winter!
Where to Stay in Chicago With Kids:
InterContinental Chicago Magnificent Mile :
The location was incredibly convenient because we were right on Michigan Avenue, close to shopping, restaurants and several of the attractions we wanted to visit. But what made it especially great around Christmas was everything we had inside the hotel itself. There is a Starbucks connected to the hotel, multiple restaurants onsite, and probably the biggest win with kids - an indoor pool. The week we were there they did a dive in movie night and served fresh popcorn and other snacks and drinks.
On a freezing Chicago day, there is something so nice about getting back to the hotel and knowing you don't necessarily have to bundle everyone back up just to find dinner or grab coffee the next morning. And after a full day of sightseeing, our kids were perfectly happy ending the night swimming in the pool.
For families visiting Chicago during the holidays, I would absolutely stay here again.
InterContinental Chicago Magnificent Mile is the most central and best place to stay in downtown chicago with kids. They decorate so beautifully for christmas with a HUGE tree in the lobby, have an indoor pool and even have swim in movies.
If you're visiting Chicago with kids in the winter, having a hotel with food, coffee and an indoor pool all under one roof is a HUGE plus. Even if you are not visiting in the winter, the central location of this hotel is amazing!
Why we loved it for families:
Right on the Magnificent Mile
Easy access to shopping and attractions
Starbucks connected to the hotel
Multiple onsite restaurants
Indoor pool for the kids
Great option when you want to minimize time outside in freezing weather
What activities/tours to book:
We loved this as a fun indoor break when everyone needs to warm up after being outside. It’s much more of an interactive experience than a traditional museum — kids can jump in the sprinkle pool, play mini golf, explore colorful installations and, obviously, eat unlimited ice cream along the way. 😂 It’s especially good for a late afternoon or evening when you’ve already done some sightseeing and want something easy and FUN.
This is such a fun way for kids to see Chicago from a completely different perspective, especially if they’re brave enough to step out onto The Ledge, the glass boxes extending from the 103rd floor. It’s also a great winter activity because you get the huge city views without standing outside freezing, and there are interactive Chicago exhibits before you even head up to the observation deck.
If you’re visiting Chicago in the winter, this is one of those places I would absolutely keep in my back pocket for a cold afternoon. It’s right at Navy Pier and has SO many hands-on exhibits for kids — climbing structures, dinosaur digging, art, building and tinkering. So they can actually move around and play instead of just walking through another museum.
DAY 1: Magnificent Mile + Christmas Lights + Musuem of Ice Cream
Morning: Explore the Magnificent Mile
Start your first morning by getting out and seeing Chicago. Walk along Michigan Avenue and the Magnificent Mile, which feels especially festive during the holidays with Christmas lights, decorated storefronts and plenty of places to duck inside when everyone needs to warm up.
A few fun stops with kids:
The LEGO Store
American Girl Place
The holiday displays and shops along Michigan Avenue
We wouldn't spend the entire day shopping, but this is an easy way to start exploring the city without having a super rigid schedule.
Stop at the Starbucks Reserve Roastery
While you're already on Michigan Avenue, stop at the Starbucks Reserve Roastery, the largest Starbucks in the world. Instead of just grabbing regular drinks, we turned this into a little experience. We ordered several different coffees to taste-test and got desserts for the kids so everyone could participate.
This place was 4 levels and had so much to see. The kids loved being able to see how the bakery items were cooked right in front of you. It's also the PERFECT excuse to get inside and warm up for a while.
Afternoon: Keep Exploring Downtown
Spend the afternoon walking around downtown and seeing some of the classic Chicago sights.
You could head toward the Chicago River, walk part of the Riverwalk if the weather cooperates, see the Wrigley Building and Tribune Tower, or simply wander through the downtown area and enjoy all of the holiday decorations.
The goal isn't to cram in a million attractions. Give yourselves time to explore, stop for hot chocolate and actually enjoy being in Chicago at Christmas.
Dinner: Try Chicago Deep-Dish Pizza 🍕
Your first night is a great time to knock out one of Chicago's most famous foods. Find a classic deep-dish pizza spot like Lou Malnati's or Giordano's and make dinner part of the experience. Some of these places can get extremely busy so try to go at off hours and just remember that deep-dish takes longer to cook than a normal pizza, so don't arrive with completely starving kids.
Evening: Museum of Ice Cream 🍦
Visit the Museum of Ice Cream. After spending a good part of the day walking around outside, everyone will be ready to get warm and this gives the kids something really fun to look forward to at the end of the day.
The Museum of Ice Cream is much more of an interactive experience than a traditional museum. There are colorful rooms, games, photo spots, the giant sprinkle pool and plenty of ice cream along the way. Plan for around 90 minutes. The end also has a ballpit and small playspace for kids to enjoy.
➡️ Book the Museum of Ice Cream
We loved having activities like this built into our Chicago itinerary because winter sightseeing with kids is all about alternating:
outside → warm up → outside → warm up.
Ending the first night with ice cream, playtime and absolutely no more walking in the cold is a pretty great way to do it.
DAY 2: Christmas Market + Ice Skating + Holiday Show
Morning: Millennium Park
Start around Millennium Park. See Cloud Gate/The Bean, walk through the park and check out Chicago's big Christmas tree if it's up during your visit. Then go ice skating.
Ice Skate at Millennium Park
Skating downtown surrounded by Chicago's skyscrapers is one of those activities that feels particularly magical around Christmas. I would try to book an earlier skating time if possible before everyone gets cold and tired. Skating is free but YOU DO NEED TO BOOK IN ADVANCE! If you do not have skates, you can rent them for about $16-20. I linked the website below where you can find out all of the updated information.
TIP: Holiday activities and skating schedules can change each year, but you can check them on Chicago’s Official Website.
Lunch: Get Chicago Deep-Dish Pizza
You can't take the kids to Chicago without doing this at least once. I'd make this part of the experience rather than just grabbing lunch. Our pick would be Lou Malnati's Pizzeria on Michigan Avenue, although Giordano's is another classic Chicago option. Order a true Chicago deep-dish pizza and be prepared to wait — these pizzas take longer to cook than regular pizza.
For kids, that's part of the fun! And when you are in Chicago. You HAVE to try Chicago pizza.
Afternoon: Christkindlmarket Chicago
Then head to Christkindlmarket Chicago. This is Chicago's traditional German-style Christmas market. The market is free to enter and is filled with wooden stalls selling ornaments, gifts and European-style Christmas goods, plus lots of food. You'll smell roasted nuts, pretzels, bratwurst and spiced drinks as soon as you walk in.
We loved spending a few hours here. Walking around the stalls, getting hot chocolate and buying a christmas ornament. It is a great experience and feels similiar to the European christmas market (the closest thing you will get in the US).
What should you actually DO at Christkindlmarket with kids?
I'd make it a little scavenger hunt:
Let each kid choose one Christmas ornament/sourvenir.
Get a giant German pretzel.
Try bratwurst or another German food you've never ordered before.
Find the year's collectible Christkindlmarket mug.
Get hot chocolate for the kids.
Look for the big nutcrackers and Christmas decorations.
Let everyone pick one sweet treat to split.
I think the trick with Christmas markets and kids is giving them something to look for/do, rather than asking them to happily browse handcrafted ornaments for two hours. Depending on how cold it is and what you can handle, just make it a loose plan. Don’t plan to spend your whole day here. We were able to walk to the market from our hotel but it was so cold, we ended up taking an Uber back.
Evening: See a Christmas Show
Finish the night with a holiday show. One of the best-known Chicago Christmas traditions is A Christmas Carol at Goodman Theatre.
For 2026, it runs from November 13 through December 31. One thing parents should know: children under five aren't permitted, so this particular show is better for families with school-age kids. I love adding a show to a city trip because it makes the evening feel like an event rather than just another restaurant reservation.
Some other family-friendly shows:
- The Nutcracker: Only shows on certain days. This year is it December 18-20. See the full schedule + purchase tickets
- Sound of Music sing-a-long: Plays at The Music Box around Thanksgiving. (Nov 26 to Dec 3). See the full schedule + purchase tickets.
DAY 3: Lincoln Park + Sledding + Holiday Lights
Morning: Lincoln Park
Head up toward Lincoln Park and spend some time outside. If Chicago has snow during your trip, this is when I'd go sledding.
Go Sledding at Cricket Hill
Cricket Hill at Lincoln Park is one of Chicago's classic sledding hills and would be SO fun if you happen to get fresh snow. This is obviously weather dependent, but IF THERE'S SNOW: DROP EVERYTHING AND GO SLEDDING. You don't get a magical snowy Chicago day on demand, so if you have one, take advantage of it. Soldier Field is another well-known option for sledding in the city.
If there isn't snow...
Choose either:
1. Lincoln Park Zoo — easy to combine geographically with Cricket Hill.
2. One of Chicago's big museums if you want an indoor day.
-Chicago Children's Museum Entry Ticket
-Willis Tower Skydeck and The Ledge
Personally, for a Christmas-specific itinerary, I would choose the zoo if it not that cold!
Evening: ZooLights at Lincoln Park Zoo
ZooLights turns Lincoln Park Zoo into a huge Christmas light display with illuminated animal figures, holiday installations and seasonal activities. It gives you another Christmas experience, rather than just sightseeing that happens to be done in December. I would time it for late afternoon so you're already there when it gets dark.
Optional: One more fun Chicago Christmas idea: Try to spot the CTA Holiday Train 🚆🎄
Chicago's transit system traditionally runs a wildly decorated holiday train during the Christmas season. It's covered in lights and decorations and even has Santa along for the ride. You dhuldn’t necessarily structure your entire itinerary around catching it, but if your dates line up with the schedule, kids would think this is AMAZING.
THE 3-DAY ITINERARY AT A GLANCE
DAY 1 — MAGNIFICENT MILE
Magnificent Mile → LEGO Store + American Girl → Starbucks Reserve coffee/dessert tasting → Christmas lights → Museum of Ice Cream
DAY 2 — CHRISTMAS CHICAGO
Millennium Park → ice skating → Chicago deep-dish pizza → Christkindlmarket → A Christmas Carol
DAY 3 — LINCOLN PARK
Lincoln Park → sledding at Cricket Hill if there's snow → Lincoln Park Zoo → ZooLights
This is the perfect balance so you're not dragging kids from landmark to landmark. Every day has something the adults want to experience plus something the kids are legitimately excited about.
FAQ
Q: Is Chicago worth visiting around Christmas with kids?
A: Absolutely. Chicago feels especially fun during the holidays because you get the big-city Christmas atmosphere without needing to plan every minute around holiday events. You can ice skate downtown, visit Christkindlmarket, see a Christmas show, walk along the Magnificent Mile, and then mix in indoor activities when everyone needs a break from the cold.
Q: How many days do you need in Chicago with kids at Christmas?
A: I think 3 full days is perfect for a first trip. It gives you enough time to see the holiday highlights without packing so much into each day that everyone is exhausted. If you have 4 days, even better you can add one of Chicago’s bigger museums or slow the itinerary down a little.
Q: Is Chicago too cold to visit with kids in December?
A: It can definitely be cold, but I would not let that stop you from going. The key is planning your days so you are not outside for hours at a time.
Q: We tried to alternate between outdoor sightseeing and indoor activities — walk around for a while, warm up at Starbucks, shop, eat lunch, visit the Museum of Ice Cream, etc.
A: Good coats, hats, gloves and warm shoes make a HUGE difference.
Q: What should kids wear in Chicago in the winter?
A: Layers are your friend. We would pack: Warm winter coat, Hat, Gloves or mittens, Scarf or neck warmer, Warm socks, Waterproof or weather-resistant shoes & Layers underneath clothing. If there is snow in the forecast and you plan on sledding, definitely bring snow pants or waterproof pants for the kids.
Q: Do you need a car in Chicago with kids?
A: No. I would actually avoid renting one if you are staying downtown. We walked a lot and used public transportation or rideshares when needed. Staying somewhere central, like the InterContinental Chicago Magnificent Mile, makes this much easier because you are already close to so many attractions, restaurants and shops.
Q: Where should families stay in Chicago at Christmas?
A: We stayed at the InterContinental Chicago Magnificent Mile and would absolutely stay there again. The location was great, but what we appreciated most in the winter was having so much inside the hotel. There is a Starbucks attached, multiple restaurants and an indoor pool for the kids. When it is freezing outside, not having to bundle everyone up again just to grab dinner is SUCH a nice perk.
Q: What are the best Christmas activities in Chicago with kids?
A: Our favorites include:
Christkindlmarket Chicago
Ice skating at Millennium Park
Seeing a holiday show like A Christmas Carol
Walking the Magnificent Mile to see the lights
Visiting the Starbucks Reserve Roastery
Shopping at the LEGO Store and American Girl
ZooLights at Lincoln Park Zoo
Sledding if there is snow
Looking for the CTA Holiday Train
And we also loved mixing in non-Christmas activities like the Museum of Ice Cream.
Q: Is Christkindlmarket Chicago good for kids?
A: Yes, but I would give kids something to actually DO while you are there. Let them choose an ornament, try a giant pretzel, find the collectible mug, get hot chocolate or pick a sweet treat. Christmas markets can get boring pretty quickly for kids if the plan is simply to walk around looking at booths, so turning it into a little food-and-shopping scavenger hunt makes it much more fun.
Q: Is the Museum of Ice Cream worth visiting with kids?
A: We thought it was a great addition to a winter trip because it gives everyone an indoor break. I actually think it might of been my kids favorite thing we did this entire trip. I would not necessarily make it the first thing you do in Chicago. Instead, save it for a late afternoon or evening after you have already spent time walking around outside. It is colorful, interactive, very kid-friendly and there is plenty of ice cream along the way.
Q: Where should you get Chicago deep-dish pizza with kids?
A: You really should try deep-dish pizza at least once while you are in Chicago. Lou Malnati’s and Giordano’s are two of the most well-known options and both are easy choices for families. They are popular for a reason though so remember to factor in wait times or go during off peak hours!
Q: Is Chicago walkable with kids?
A: Downtown Chicago is very walkable, especially if you stay near Michigan Avenue. That said, distances can feel MUCH longer when it is 25 degrees outside. We tried to group activities by neighborhood and avoid walking back and forth across the city unnecessarily. If everyone was cold or tired, we had no problem grabbing a rideshare.
Q: When is the best time to visit Chicago for Christmas?
A: Anywhere from late November through December works well. Going earlier in the season can sometimes mean slightly smaller crowds, while the weeks closer to Christmas feel especially festive. Just remember that some holiday events, markets and shows have their own seasonal dates, so always check schedules before booking your trip depending on what you want to do!
Q: Is Chicago at Christmas expensive?
A: It can be, but you can mix expensive activities with plenty of cheaper or free ones. Walking the Magnificent Mile, seeing holiday decorations and visiting Millennium Park do not have to cost much. Then you can choose a few things to splurge on, like a show, ice skating, the Museum of Ice Cream or a special dinner. We usually prefer to spend money on the experiences we are most excited about rather than trying to book something every hour of the day.
