7 Things I Can’t Wait to Do In Chicago This Season

Other than the cold I love the holiday season, chunky sweaters and cozy drinks, I love wrapping myself up in a blanket and watching holiday movies. But this year since I’m new to Chicago and this is my first Christmas season I thought it would be fun to look into outdoor activities going on around the city, so here is my list of upcoming events I’m most excited to participate in. 


After spending Christmas in Germany my perception of the magic of Christmas has forever been altered.  I had such an amazing time exploring the beautiful Christkindlemarkets in all the little German towns that coming home and having a normal American Christmas has been a bit lackluster.  Ever since that trip around this time I get the worst travel bug longing to go back, so when I found out that Chicago puts on their own Christkindlemarket I was overjoyed.  Held in the Daley Center they have all the traditional German fares as from trinkets, to food and of course the Gluhwine.  The stalls are even similar to the ones in German.  I’m so excited to feel that nostalgi magic in the area when I get down to the market.  

Navy Pier Winterfest

Not only does Chicago have their very own German Christkindlemarket but Navy Pier also puts on their very own winter wonderland.  Winterfest is 170,000 square feet of winter-themed fun, from carnival rides to indoor ice skating Winterfest is a great activity for the whole family. 

ZooLights at Lincoln Park Zoo (Free)

Who doesn’t love a free activity?  One of my favorite Chicago activities to bring out of town guests to the zoo, its such a pretty little zoo with a great selection of animals.  So of course with just a little holiday cheer the zoo becomes absolutely magical.  They cover the grounds in more than two million lights and larger than life illuminated animal designs.  Bring your mulled wine and hot chocolate and see the penguins and polar bears along with some festive lights.

Joffrey Ballet

As a ballerina the Nutcracker is a staple in the holiday season. I spent my entire childhood sitting in auditoriums rehearsing for the Nutcracker each and every Christmas season, so I think that’s why this is such a special time of year for me.  I get so excited to go and watch ballet troupes perform this magical ballet.  While I was living in Syracuse I saw the Moscow ballet as well as the Syracuse City ballet but this year I am so excited to experience the Joffrey here in Chicago.

Macy’s Holiday Windows

When you think of New York City at Christmas time I always think of skating at Rockefeller Center and the Macy’s holiday windows.  It’s so fun to walk through Harold Square in the snow and see these beautiful displays.  But New York isn’t the only Macy’s that shares these stunning holiday exhibits.  The Macy’s on State St in Chicago also creates beautiful window displays you can experience while doing your last minute Christmas shopping.

Skating in Millennium Park 

At the top of my list every year at Christmas time is an evening at the ballet and outdoor skating.  There’s just something so magical about lacing up your ice skates and taking a couple laps with your loved ones.  I am the most excited about the opportunity to skate in one of my favorite parts of Chicago this year.  Millennium Park sets up an ice rink just below The Bean and I honestly couldn’t think of a more perfect location.  In the heart of the city with my favorite skyline surrounding me truly sounds like a dream.

Music Box Christmas Double Features 

Finally on those really chilly days who doesn’t love to curl up and watch some festive movies? The Music Box Theater, a beautiful historic theater is showing a double feature of two of my favorite classic Christmas movies, It’s a Wonderful Life and A White Christmas.  Along with these two movies that why are playing every night the theater is also showing many other family favorite holiday movies. 



    • itsjustjessa
      December 18, 2018 / 8:38 am

      Oh thank you! They’re from Target! Such a steal but unfortunately they rip so easy!

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