Chicago Holiday Weekend With Kids

I’ve been wanting to take the kids to Chicago for years, and finally, the opportunity arose to take them on one of the first big holiday weekends of the year: Thanksgiving Weekend. So, I knew it was going to take some planning (it all started with this Chicago Holiday Bucket List). Here’s all that we did during three days in Chicago!

UPDATED: This post was first published in 2018 and has been updated in November 2025 with current prices and business info.

Disclosure: This post contains affiliate links. At no additional cost to you, if you click the link and/or make a purchase, I may receive a small payment for referring you. 

Note: A portion of our trip was hosted, while we paid for most of the experiences.

Trees & caroling in Chicago

There were three places we had planned on seeing Christmas trees. For a meal under a giant Christmas tree, you’ve got to head to Macy’s Walnut Room. Many people go just to take a picture. We went on a Friday night and expected a terribly long wait (it was Black Friday), but got in pretty quickly.

Fairy princesses strolled the room during the meal, granting wishes and handing out wishing stones. It was an unexpected experience that my daughter particularly loved. The service, by the way, was fantastic.

And what should you try at the Walnut Room? Get the famous chicken pot pie. 

To see trees with an around the world theme, head to the Museum of Science & Industry. Their Christmas Around The World and Holiday of Lights display is full of impressive details. I liked looking at festive trees, but my kids were not interested (due to the fact that the rest of the museum was so stinking amazing). On the weekends, there are performances I wish we could’ve seen.

There’s also a gorgeous, giant tree that’s the centerpiece of it all. On the hour and half-hour is a “snowfall.” We hung around to see it once. It’s not too exciting, at least not for a 7-year-old.

The extra exhibitions and experiences are a considerable add-on. We did the coal mining experience and it was OK (not totally sure it was “$80+ OK,” though).

The extra I do think was worth it was the $5 toy building assembly line. The tops the kids made work great. The machine did have a few moments of not working, so it wasn’t a smooth process. NOTE: I’m not totally sure if they still have this experience, but if they do, I recommend it.

For the ultimate Christmas tree experience, head to Millennium Park. There’s ice skating with the giant Christmas tree lit up in the background. We visited on a Friday night and they had live Christmas music by “Cloud Gate,” AKA, The Bean. Everyone in the crowd sang along. These concerts happen every Friday night in December.

Chicago is a great city to see holiday lights. We happened upon gorgeous displays on walks from our hotel, Loews Chicago. Two great trees can be found on Wabash Avenue by the river, right by the Ghirardelli store.

Holidays at Chicago museums

Museums were definitely on our itinerary, especially since we just weren’t sure how nice the weather would be so we planned a lot of indoor stuff. The museums we visited had their own Christmas decorations to enjoy. I already mentioned Museum of Science & Industry, and that was, by far, the most decorated place of the three we went to.

The Field Museum had holiday lights set up in the main lobby and on stairwells, plus some wreaths hung up. It was minimal but done really well.

The extra exhibitions at The Field Museum are a considerable add-on. Admittedly, the one we chose was not worth it.

The Art Institute of Chicago, the iconic lions out front have wreaths placed around them. If you head to the Thorne Miniatures Room, a couple of the rooms had some Christmas-y décor added to them.

If you take little ones to Art Institute of Chicago, you’ve got to stop first at the Ryan Learning Center in the Contemporary Building. There, in addition to some great art activities, you’ll find the JourneyMaker center, where kids can create a mini tour of the museum based on a theme they choose and the artwork they choose to see within that theme.

The kids loved it, and it made an extremely large museum manageable for a child. We had four stops on the tour – both kids chose the creatures theme – and it took us to quite a few galleries, including my favorite, the Impressionists area. In about an hour, we had found the art, did the little activities associated with each stop and made it back to the learning center to collect their prize (a postcard of their choice).

The good news about visiting this art museum with kids is that they’re free if they’re under 14!

Chicago restaurants decorated for Christmas

Most Chicago restaurants we visited had some sort of decoration, but one stood out for the decor and another stood out for the food: The Walnut Room.

I’ve already mentioned the Walnut Room at Macy’s, but it’s worth repeating. The giant Christmas tree is a show-stopper, for sure, but the food is very good too. And, it’s kid-friendly with a menu for the little ones.

Another downtown restaurant we enjoyed was the family-owned Tortoise Supper Club.

While there was some classy holiday decor, the memorable thing for us was the food during our visit. It’s not as kid-friendly, in the sense that there is no kid’s menu or kid portions, but the staff warmly welcomed my kids and the other families in the restaurant.

I’ll write more about it soon, but if you do find yourself there, my tip to you is to get the dessert (key lime pie or tortoise pie).

Ice skating in downtown Chicago

Time did not allow for us to fit in a trip to an outdoor iceskating rink in Chicago, though there are two that were within walking distance of our hotel, Loews Chicago. The one at Millennium Park is traditional oval shaped with a very charming Christmas tree in the background.

The other is at Maggie Daley Park, which is just a bridge walk from Millennium Park. It’s an ice skating ribbon, which looks a little more fun than just going in loops.

We skipped the ice skating, though, and went straight to the amazing playground at Maggie Daley Park. I think we made the right call on a particularly mild winter day.

Christmas while you shop in Chicago

The Christkindlmarket was on my wish list to visit for years. Modeled after German Christmas markets, it’s an outdoor market with vendors selling gifts, food, and drinks.

It’s very charming, in theory, but the crowds are overwhelming. I was warned by many to go early, and man, did I try to get there first thing one morning. We ended up arriving about 30 minutes after it opened, and it was already packed.

One particular aisle was crammed, and we shuffled our way barely seeing the booths. My kids still enjoyed it, and found souvenirs for themselves and a gift for one aunt.

I did, at least, have some tasty pastries and gluhwein, so it wasn’t a total wash.

Christmas is everywhere in stores, and Chicago retailers do it up well. Downtown, you’ll want to check out Macy’s window displays of exquisite scenes.

Where to stay for all the Chicago Christmas fun

I partnered with Loews Hotels for this trip and found the downtown Chicago location to be absolutely ideal for my family’s trip. Many of our destinations, like Millennium Park, are within walking distance.

In the winter, Loews Chicago offers the Snowed Inn package (now called Arctic Dreams) for families. They also set up a cute tent and campfire set for the kids to play with.

Can’t beat the view, either! That’s Navy Pier in the distance, with the big ferris wheel lighting up the background.

If you want to consider a hotel in a different neighborhood, there is no shortage of options.

Plan a Chicago Getaway

Want to visit Chicago with your family? Here are a few additional posts to help plan things. Start with my Chicago Holidays Bucket List – there’s quite a bit on the post that isn’t just for Christmas time in the city, too!

• Staying In Downtown Chicago With Kids At Loews
• Dining With Kids In Chicago
• Tips For Visiting 3 Big Chicago Museums With Kids

Try some of these tours if you want to see more of Chicago when you’re visiting during the holidays: