7 Ways to Have a Magical Christmas Trip in Chicago with Kids | Things to do With Kids in Chicago at Christmas

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7 Ways to Have a Magical Christmas Trip in Chicago with Kids 

I am not sure what it is, but big cities during Christmastime get me so happy. There seems to be so much magic. We headed to Chicago for a Christmas quick getaway to experience just that. We have been to Chicago lots but never as a family during Christmas!

You would be surprised just how much there is to do in Chicago during Christmas as a family. We spent 2 full days & were able to get a lot done & thoroughly enjoy ourselves. This itinerary would be great for a weekend holiday getaway! 

Please note, during the time of our visit it was 2021 & some things I had planned were not happening or modified due to the pandemic. But I will add in those activities for future readers.


Price: Free
Location: 50 W Washington St.

This is an absolute Christmas in Chicago must. This was my second time to the market, but my first time with the whole family. It is a recreation of German Christmas market. There are places to shop & they are known for their food & drinks. It is all set up so cute with little cabins. You can't go to Christkindlmarket without getting one of their mugs & hot chocolate! There is now 2 Christkindlmarkets in Chicago, one at Wrigley Field & the one we went to & which is on Washington St. 

Watch out for the pigeons, you'll know what I mean when you go ;) 

thing to do with kids in chicago at christmas


Price: $13 Monday–Thursday
$15 Friday-Sunday & Holidays
$10 Skate-aide (under 42 inches)

Location: 201 E Randolph St.

If you have ever been to Chicago chances are you have been to "The Bean" it is a Chicago landmark. Millennium Park Skating rink is directly below "The Bean" it makes for the perfect Chicago backdrop. Nothing says winter/Christmas more than ice skating. I'll admit it was the first time for me on skates in years & years. I was a little rusty! The girls did great. I got Kensley one of the skating aids. They are little penguins that you push to help keep your balance. Only a few are available to rent, so they may or may not be available but I highly recommend getting them for young ones. Kensley ended up giving hers to a little girl because she felt confident doing it on her own! There is also a gorgeous Christmas tree right by the rink, perfect for photos! *Note: at the time of this post ice skating was by reservation only, you can do so right online.*

thing to do with kids in chicago at christmas


Price: Free with the exception of purchase of food at The Walnut Room if you get a reservation

Location: 111 N State St.

Macy's is the unofficial department store of Christmas. Every year Macy's in Chicago has the most beautiful window displays. They are interactive & so so well done. Not to mention the exceptional decor both outside & inside. You feel like you're in Miracle on 34 Street.

thing to do with kids in chicago at christmas

thing to do with kids in chicago at christmas


At a  Macy's this pretty you just know the Santa experience is amazing. & let me tell you it exceeds ALL expectations. Reservations are required {you can do it right online} but it doesn't cost anything unless you buy the photos. You enter in the children's department through huge wood doors with Santa carvings in them. There is an interactive hallway for kids to play while waiting for Santa. It was next level & I don't know how we can ever visit another Santa again after this experience! *As of Dec 2021, masks are required everywhere & during photos in Santaland*


A few years ago I went with some girlfriends to Chicago during Christmas & went to the top floor of Macy's to look at the Christmas everyone had said we HAD to see. I was awe-struck, it was absolutely breathtaking. We had no idea that it was also a restaurant! You could dine around the gorgeous Christmas tree & I knew right then that I had to come back & take my family, they would love it so much. Let me start by saying there are coveted reservations. They are HARD to get. I got on the day they opened, I want to say it was the 1st of October & some days were already so booked up! Next, you are for sure paying for the experience here. The food was not at all bad, but not as good as we were expecting either. We all got their famous pot pies! They really make the experience magical for kiddos. There is a fairy that comes around. They do special things for food like the girls' pot pies had stars for the crust. They also had such fun desserts as well, like Kensley got a build your own snowman ice cream! This was the highlight of our trip & I can't recommend this as a must-do, more!


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♬ It's Beginning to Look a Lot like Christmas - Michael Bublé

Location: 11 E Walton

Finding a place to stay in Chicago can be daunting. Especially a family-friendly hotel that has room for your family, too! The Waldorf earned its name in the luxury hotel world for a reason. The treatment as soon as you step out of your car is next level. The Waldorf hits the mark for Christmas decor too, keeping the Christmas magic going for your trip. They have an amazing courtyard with a giant Christmas tree in the center. I loved the courtyard as I didn't have to worry about a crazy busy street with unloading the kids! Their lobby looks amazing & smells delicious. If you have stayed at a Waldorf you know that smell! When we stayed we did their Winter Escape package. This is ideal for families with kiddos! You get upgrades & free theatre snacks with an in-room movie! They had the fireplace going for us, robes for all three kids & even had a crib with a book, a baby essentials travel pack & a diaper genie all ready for us! They had thought of everything! The girls kept saying they felt like they were in Home Alone: Lost in New York! At the end of the night, I texted the concierge & they even helped our elves come back with a little Waldorf Astoria teddy bear. We got room service for breakfast which was delicious but they even have a little cafe right on property! If you are wanting that luxe, Home Alone hotel stay feel, The Waldorf is where you have to stay!

7. Water Tower

Carriage Ride

Price: Varies by carriage
Location: Chicago Water Tower

Take a horse-drawn carriage ride to look at the lights around the city! It is so magical to do this! Our driver had the coziest blanket to keep us warm when I went with my friend & had Christmas music playing. It truly was magical! {this was not running during our family trip in December 2021}

Christmas Lights

All the lights around the Water Tower are amazing & make for the best festive photos!

Bonus: If you plan ahead enough, get tickets to see the Joffery Ballet Nutcracker!

Christmas in Chicago truly can be magical. I wish it would have snowed but hey, you can't have it all can you? Have you been to Chicago at Christmas? What did you do?

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