Chicago at Christmas with Kids

If you’re considering visiting Chicago at Christmas time to experience all of the festivities, and you’re looking for things to do with kids, you’re in the right place!

I grew up just over an hour north of Chicago, so we visited many times during the Christmas season when I was a kid. I realized this year, though, that I had never taken my own kids to enjoy the holiday season in the Windy City, and I knew that had to change.

So this year I took my two oldest kids out of school on a Friday to take a mini road trip to Chicago toward the end of November. All of the Christmas decorations were up, and we even hit opening day for a few of the major holiday events!

We spent about 24 hours in Chicago, only staying in a hotel for one night, but I feel like we packed a lot into our short time there.

If you’re planning to stay for a full weekend or even a long weekend, I have a few suggestions for things we didn’t get to that you could easily include in your itinerary to round out your visit.

Here are all the best things to do in Chicago at Christmas with kids to get in the holiday spirit!

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Where to Stay

We stayed at the InterContinental Chicago Magnificent Mile by IHG. I have one of the IHG credit cards, and one of the perks of that card is one free night every year. Mine expires soon, so I decided to use it on our trip to Chicago!

I picked the InterContinental Chicago because the pictures looked so beautiful, and I had read that it was very family-friendly.

I absolutely fell in love with this hotel during our short stay. From the moment I handed off my car keys to the valet, every staff interaction I had was so friendly, warm, and welcoming.

Our room was ready so early, too, which was an unexpected surprise. We arrived around 11:30 a.m. and I made use of the valet parking, I checked in with the front desk in hopes of storing our bags while we explored the city, but was delighted to learn that our room was already prepared for us.

We were able to drop our bags off in our room, freshen up, and get ourselves situated for a day of exploring.

Another family-friendly feature of the InterContinental was that they have family-friendly Dive In Movie nights every Friday and Saturday from 6-8. They have huge pool floats, popcorn, and drinks, so you can enjoy the movie while floating in the pool, or lounge in the tiered seating above the pool. So cool!

The location is excellent, too. It’s right on Grand Avenue near the RIverwalk and among some of the best shopping, restaurants, and activities in Chicago.

Just a note: valet parking was $88 when I stayed, and valet parking is the only option. You can choose to self park off property if you want, too.

Budget or Mid-Range Hotels

Having grown up just a short distance from Chicago, I don’t have a lot of personal recommendations for hotels.

However, here are a few tried and true hotel brands that I usually book as a mom of 4 that have more spacious options for families that are a bit more budget friendly AND are still in the heart of downtown on or near the Magnificent Mile.

Things to Do in Chicago at Christmas with Kids

There is so much to do in Chicago with kids all year round! In fact, I have an entire separate blog post dedicated to things to do in Chicago with kids.

This particular post, however, is dedicated specifically to Christmas and holiday related things to do in Chicago, and not necessarily 1 or 2 night events - things you can do throughout the entire holiday season in Chicago.

I’ll also include a bulleted list of the activities we didn’t get around to that were on my radar that you could do if you’re staying longer.

Christkindlmarket

The Christkindlmarket is a longstanding holiday tradition in Chicago. I remember visiting the market when I was a kid, so it’s fun to come back with my own kids!

The Christkindlmarket is a German style Christmas market with food, hot chocolate, handicrafts, festive music and holiday decorations.

It’s a great place to go to try food from around the world, buy souvenirs or Christmas gifts, or just to enjoy the holiday atmosphere and get in the Christmas spirit!

The market is open from November 21-December 24 in 2025, and you can check the hours here. The three locations are Chicago, Aurora, and Wrigleyville. We visited the Chicago location in Daley Plaza.

They only let a certain number of people into the market at a time for safety (otherwise it gets very crowded), so you may have to wait 15-20 minutes in line before getting in. Many vendors accept credit cards, but some only accept cash, so be sure to bring some cash with you!

Macy’s on State Street

Macy’s on State Street is another fun place to take kids! Before even entering the department store you can enjoy the window displays which pay homage to Marshall Field’s with the theme: “The Most Wonderful Stories Start Here.”

Inside, you can enjoy lots of festive holiday displays, do some Christmas shopping, or enjoy a meal in the Walnut Room under the giant Christmas tree. You’ll need to make reservations ahead of time.

Finally, if you have younger kids, you can visit Santa on the 5th floor. You do need to make reservations online ahead of time.

Ice Skating at Millennium Park

My kids’ favorite activity was ice skating at Millennium Park. The outdoor rink is situated below the iconic Cloud Gate sculpture (The Bean), and surrounded on the other 3 sides by Chicago’s gorgeous skyline, making it an idyllic place to skate.

It is free to skate Monday through Thursday, and on the weekends the 11:00 a.m. time slot is free, but it’s $5 per person after that. You can bring your own skates, or rent them for between $17 and $21 per person. You can also rent a Skate-aide for young children, and there are storage lockers available for $2.

You must reserve your time slot ahead of time, even if it’s one of the free sessions, and the time slots are every 2 hours. You get 90 minutes to skate, then there is a half hour where they clear the ice to clean up and get the next round of people checked in.

Food and drink is available rink-side at Momentum Coffee and Millennium Hall so you can warm up with a meal or hot chocolate after you skate.

I had never taken my kids ice skating before this, so we were all a little bit shaky and holding onto the railing the first few laps around the rink.

By about our 3rd lap, we were all more comfortable letting go, and cracking up at how wobbly we were, but still having the time of our lives.

We booked the 3-4:30 p.m. time slot on a Friday, and the timing was perfect! The sun was just starting to set by the end of our session, so the pre-sunset sky was stunning as a backdrop to the Bean and the skyline. It wasn’t too crowded, and the weather wasn’t too cold for late November. We were even shedding our coats by our 3rd lap around!

This was such a memorable experience with the kids, and I would highly recommend it, even if you’re not a big ice skating family.

Hot Chocolate Flight at JoJo’s Shake Bar

You’ll find tons of great spots to enjoy hot chocolate in Chicago around the holidays, but we decided to try JoJo’s Shake Bar because they put up a Winter Wonderland tent each year with Christmas lights, a tree, a sleigh, and tons more holiday decorations!

There are tons of seasonal treats to choose from, but I think one of the most fun options for kids is Rudolph’s Hot Chocolate Flight. It’s $18 for 4 small (but filling) hot chocolate drinks with oversized marshmallows and other toppings.

Flavors are:

Toasted Marshmallow
Double Chocolate
Salted Carmel
Peppermint

My personal favorite was the salted caramel! You can order any of these options individually, plus there are several other holiday themed drinks like

Winter Wonderland Shakes
Themed Cocktails (Frozen Polar Espresso, anyone?)
Flavored Hot chocolate.

This was such a fun and festive way to get in the holiday spirit in Chicago!

Enjoy Michigan Ave

If you’re like me and haven’t started your Christmas shopping yet, be sure to stroll Michigan Avenue and duck into all of shops along the Magnificent Mile! From the American Girl Store to the LEGO store, the Harry Potter store, H&M, Zara, and more, you’ll find something for every member of the family.

Beyond the great shopping, you’ll find great window displays, holiday decor, and a series of Christmas trees up and down the street.

It’s a festive place to be in the weeks leading up to Christmas!

Coffee at Ralph’s Coffee Bar

Ralph’s Coffee Bar is the small coffee shop in front of the Ralph Lauren store on Magnificent Mile. Having a “Ralph Lauren Christmas” has been all over social media this year, so I thought this would be the perfect spot to grab my morning latte.

I ordered the gingerbread latte, and my kids got hot chocolate and croissants. They top off the gingerbread latte with some gingerbread man latte art, which was adorable!

A few tips for visiting with kids:

The shop is small with not a lot of seating, so either plan to just stop in to get your drinks to go, or try to get there right at opening time to ensure you get a seat.
Check the website for current opening times, but on the day we visited, it opened at 8. We arrived at 8:15. The seats were almost all taken, but there were only a few people ahead of us in line. By the time we sat down with our drinks and food around 8:30, there was a line going out the door!
If you have a stroller and you plan to sit down, consider folding it up before you get inside the store so you don’t have to try to navigate through narrow spaces between tables.

Harry Potter Store

The Harry Potter store in Chicago opened earlier this year, so it’s still a very new and therefore a very popular spot.

Note: we arrived 10 minutes before opening on a Saturday morning, and there was already a short line forming outside. By the time we left, there was already a virtual queue to get into the store. If you’re planning to visit on the weekend, I would suggest arriving right at opening time. I’m guessing it would not be as busy on a weekday, but of course, I can’t say for sure.

This was our first time visiting, and I was so excited to go since all 3 of us are big Harry Potter fans. (I’ve taken my daughter to the Wizarding World of Harry Potter at Universal Orlando for her 9th birthday trip, and to Scotland for a Harry Potter themed 11th birthday trip! My son is just getting into the books now).

They have a Christmas Tree Trail in the store, and kids can fill out the scavenger hunt as they walk through the store. There is a letter hidden in each Christmas tree, so they have to put the letters together to solve the mystery word. Then they can turn in their scavenger hunt for a free pin! It’s a great festive activity to keep kids engaged while you check out the magical merchandise.

We loved browsing the store, and my kids got a lot of ideas for Harry Potter items to add to their Christmas list!

At the end of our visit we stopped in the attached cafe for a hot butterbeer and a butterbeer cookie.

Holiday Tea at the Drake

The Drake Hotel has an incredible holiday afternoon tea between early November and early January each year. We did the Palm Court’s Afternoon Holiday Tea one year with all of my sisters, my mom, and the girl cousins. There are a few other fun and festive options at the Drake to enjoy:

Festival of Lights Afternoon Tea in the Camellia Room
A Festive Gingerbread Display
Lavazza Holiday Tea Drink and Cookie Specials
Holiday decor and a gorgeous tree in the grand lobby

The Afternoon Holiday Tea comes with your choice of tea, and a tower of tea sandwiches and decadent cakes and desserts. Depending on the date of your visit, you may get to experience the Carolers, and you can even make Christmas Carol requests!

The Palm Court is absolutely stunning, and it’s a very fun and classy holiday experience that is also kid-friendly.