Christmas in Chicago With Teens – 6 Things To Do!

Christmas in Chicago is filled with yummy treats, outdoor activities and of course lots of Christmas lights! Come for a weekend or just for an afternoon and get into the holiday spirit with your family.

When we visited we arrived right after lunch time (so we could save some money eating lunch at home before we went) and had a hotel booked for 1 night. The hotel was in walking distance to everything we wanted to do so we parked our car in the parking garage and headed out to explore!

What we were looking for when visiting Chicago at Christmas time:

  • Visiting the Christmas market.
  • Finding fun outdoor activities (and dressing accordingly).
  • Finding at least one yummy treat.
  • Not spending a ton of money!

Christmas In Chicago With Teens Itinerary


Chicago is an awesome place to take teens to get into the Christmas spirit! We spent one night there and had an amazing time! All the kids said they enjoyed it and wanted to make it a yearly tradition. Here is what we did: 🎄JoJo’s Winter Wonderland for milkshakes 🎄Michigan Ave 🎄Christkindlmarket Chicago 🎄Ice Skating Ribbon 🎄Navy Pier 🎄Harry Caray’s for Curling and a warming hut We stayed at the Embassy Suites on the Magnificent Mile We parked our car in one of the parking garages and walked to all of these places – it was about 5 miles total but didn’t feel like it with all the things we stopped and did in between! Comment “Chicago” and I will send you our post with all the details! Have you visited Chicago at Christmas time?! ➡️ FOLLOW FOR MORE TRAVEL, FAMILY LIFE AND RVING TIPS @crazyfamilyadventure @crazyfamilyadventure @crazyfamilyadventure #chicago #chicagoatchristmas #christmaswithteens #familytravel #raisingteens @Choose Chicago

♬ Sleigh Bells (PhatCap! Trap Remix) – Ronettes

Here was our plan (a variety of these needed reservations and since we were going on a Tuesday it wasn’t a problem to book a couple days before we went – if you are going on the weekend you will most likely have to book well in advance).

1pm – Stop at the hotel to drop off our bags with the bell hop.

We stay at the Embassy Suites on the Magnificent Mile.

1:30pm – Drop the car off at the parking garage.

We bought a spot before we came which mean we saved 50% on the cost of parking our car for 24 hours. This is where we parked: Millennium Parking Garage.

2pm – Walked to JoJos for our 2pm reservation in the Winter Wonderland tent to have some fun shakes and drinks!

3pm – 4pm – Walk along Michigan Avenue to check out a few stores. Along with making a stop at the Starbucks Reserve.

4pm – 5:30pm – Walk over to the Christmas Market. Eat dinner here.

5:30 – 7pm – Stop at the car to get our ice skates and go to the ice rink! (Reservation required)

8:00pm – Walk over to Harry Caray’s tavern for Curling and a warming hut with drinks and apps!

9pm – Walk over to our hotel: Embassy Suites on Magnificent Mile

The timing worked out. However in hindsight we would have preferred to have extra time to be able to visit Macy’s before the Christmas Market. If that is something you want to do I would recommend starting an hour earlier.

Map Of Our Day

Map of the route we took in Chicago

Click here to open the map of our time in Chicago.

Details on Things To Do In Chicago With Teens During Christmas


milkshakes at JoJo's a must do at Christmas time in Chicago with teens!

This is a store that is open year round but at Christmas they have a Winter Wonderland where they setup a tent and decorate it all with Christmas decorations! I wasn’t sure if it would be cold in a tent but it wasn’t at all.

If you want to experience the Winter Wonderland go here for your milkshake!!

Milkshake – if that is what you want to call it! This is a whole on treat. A milkshake with a full cookie, cake pop, and chocolate covered marshmallow. They have a holiday one. But also have a bunch of other delicious flavors!

Don’t worry for parents they have some fun holiday alcoholic cocktails as well. The drink was good but the best part was you got to keep the cute festive glass.

They also have a full menu of food if you want to do that.

Michigan Ave

When visiting Chicago at Christmas you have to make a stop in at least a few shops on Michigan Ave! We did some window shopping and stopped in Sephora, Nike and Under Armour.

Note: The stores are so warm!! They really need to turn the heat down. In any case if you plan to spend a lot of time shopping dress accordingly.

Christkindlmarket Chicago (Christmas Market)

Kids at the Christmas market

There are multiple locations of the Christkindlmarket around Chicago. We visited the one in downtown. We went on a Tuesday so there was not a line to get in. When my sister and her family visited last year on a weekend they had to wait in line around the corner to get in!

Once in there are a variety of shops that sell really cool German inspired Christmas gifts. They also have a Käthe Wohlfahrt Christmas Store which is the one we visited when we went to Rothenburg Ob Der Tauber when we were in Germany.

There are also a variety of food stalls. With sausage, sauerkraut, potato pancakes, pierogis, pretzels and lots of different dessert options.

They are also known for their mulled wine. You pay $12 and you get a glass of wine and a cool small coffee cup style cup that you get to take home. they have a new one each year! You can also get hot chocolate in a souvenir cup.

We spent about 1 hour there. The adults could have stayed longer. For the kids that was plenty of time.

Maggie Daley Park Ice Skating Ribbon

Ice skating in Chicago on the ribbon with the buildings lit up all around.

This is a fun ice skate rink – actually a ribbon located in Maggie Daley Park. Depending on when you go it can be free (but you do need a reservation) if you bring your own skates. These dates do very so be sure to check here.

Once there you can skate around the ribbon as many times as you want during your reserved 2 hour time slot. They have a food area and lockers with an indoor bathroom.

I love how it is a ribbon and not just a big oval you are skating on. Plus the view of the buildings all around makes it a unique Chicago experience!

Navy Pier

Head to Navy Pier to check out all the light displays!

Harry Carays Tavern – Curling By The Lake

Curling at Harry Caray's tavern.

Last but not least we made our way over to Harry Caray’s Tavern on Navy Pier to do some Curling! We had to pay for Curling ($5 a person) and put down $100 to be able to sit in the warming hut next to the curling.

The good thing was the $100 for the warming hut went towards our food and drinks. We got there and got settled into the warming hut, ordered our food and drinks and headed out to play our first round of Curling.

None of us had played before so it was good they easy to follow instructions!

We played a couple rounds of Curling and enjoyed our food and drinks in the warming hut – which we had for 1 hour.

That’s a wrap on our time in Chicago at Christmas with teens! 3 of the 4 came with me (one was home sick) and all 3 of them said it was an amazing time. Melia even asked to come back for her birthday! I would call that a win.

Where To Stay In Chicago at Christmas Time

We stayed at the Embassy Suites By Hilton Chicago Downtown Magnificent Mile. Location wise we could walk everywhere we went plus they have a full breakfast in the morning.

Plus with 6 people there is enough room for all of us!

Additional Things To Do In Chicago at Christmas Time:

  • Visit the Museum of Science and Industry and see the twinkling lights and Christmas Trees at the Christmas around the world and holiday of lights Christmas Event.
  • Chicago Botanic Garden
  • Illumination tree lights at the Morton Arboretum
  • Museum of Ice Cream Pinkmas Tree Forest
  • Lincoln Park Zoo
  • Life Sized Snow Globe at Navy Pier

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There are so many great things to do in Chicago at Christmas with teens! Check our our itinerary with our top 5 picks of what to do in Chicago at Christmas time with teens!


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