Christmas in Chicago: 7 Reasons To Visit the Windy City During the Holiday Season

There is something so magical about Chicago during the holiday season. Christmas in Chicago means lights soften the everyday hustle, greenery gives life to the gray skies and glittery storefront displays dazzle passersby. Not only was the Windy City recently voted #1 Best Big City in the U.S. by Conde Nast Traveler’s 2018 Reader’s Choice awards, it also is America’s most asked about city according to Expedia in December 2017. I recently visited this award-winning destination and wanted to share with you 7 reasons why you should visit the Windy City during the holiday season.

Pin this to save for later!

Disclaimer: I am not a super excitable person. It takes a lot to make my heart flutter, so when you see me jumping up and down joyfully, you know something amazing has happened. A few weeks ago, the Illinois Office of Tourism reached out to see if I wanted to visit the Windy City in exchange for helping to promote travel to the area during the upcoming holiday season. Here’s where my eyes got big, heart grew full and head went a little dizzy…my first out-of-state press trip!

Back when I started ByTravelandError.com in 2016, I dreamt of opportunities like this, but figured it probably wouldn’t happen. Here’s to chasing after your goals! A big thank you to the Illinois Office of Tourism for making this Midwest gal very happy. Many of the below experiences I wrote about were complimentary. As always, all opinions are 100% my own.

Christmas in Chicago: 7 Reasons To Visit the Windy City During the Holiday Season

Reason #1

1. You can pretend you are in Europe while shopping and eating at the Christkindl Market! If you’ve ever been to Europe during the holiday season, you may have had the joyful experience of visiting a Christmas market. Inspired by the Christkindl Market in Nuremberg Germany, Chicago started their own in 1996. Now there are three markets in Chicagoland and Milwaukee, bringing holiday cheer to all who visit.

The food and drink booths include traditional German cuisine, including brats, sauerkraut, potato pancakes, pretzels, beer, glühwein (hot spiced wine), and more. The shopping vendors sell classic German products like nutcrackers, cuckoo clocks, and beer steins, as well as holiday gifts like ornaments, mugs and embroidered linens. There were so many things here that reminded me of Christmas Eve at my Grandma and Grandpa’s house, as my family has German roots. I had the opportunity to visit the downtown Chicago location on opening day and the market was packed within a few minutes of the gates being unlocked.

Reason #2

2. You can regain your childlike belief in the magic of Christmas at Macy’s. Oh my goodness, I had no idea of the breadth and depth of holiday traditions at this huge department store. Every single year, Macy’s brings a new Christmas theme to life all throughout their multi-level store. For $12, you can book the Macy’s Holiday Traditions Tour which will teach you about the history of the store and their Christmas magic.

The tour guide was so enthusiastic and passionate about Macy’s!

The famous Walnut Room with the Great Tree is a popular attraction.

You can view the infamous storefront windows, taste Frango Mint Chocolate (YUM!!!) and take a picture in front of the Great Tree in the Walnut Room. The tour guides are very entertaining and knowledgeable. Shop ’til you drop while believing in the magic of the Christmas season at Macy’s!

Just LOOK at that gorgeous ceiling. Take the tour to find out it’s history!

Reason #3

3. You can learn about how the holidays are celebrated all over the world at the Museum of Science and Industry’s Christmas Around the World Exhibit. The sheer size alone of this museum is awe-inspiring. It’s the largest science center in the western hemisphere and is suitable for all ages! While the museum features multiple interactive exhibits like Science Storms, Numbers in Nature, and YOU! The Experience, the must-see holiday exhibit is Christmas Around the World.

As you ride the escalator up to the main level of the museum, you will be greeted by a four-story massive Christmas tree. Surrounding this beautiful tree are fifty (!) more Christmas trees, each representing a different country. The ornaments and decor give viewers a taste of each country’s holiday traditions, while the plaques below each tree explain in more detail what Christmas and the holidays are like in that area of the world. For a travel-loving gal like myself, I was absolutely in love with this whole exhibit. I reallllllly geeked out at this whole experience and can’t wait to go back and use my Chicago City Pass to spend a full day at this magical place.

I’ll be back, MSI Chicago!

Reason #4

4. You can spend time with your loved ones over ridiculously delicious food. Did you know that there are over 7,300 restaurants in Chicagoland, 22 of which are Michelin starred? That blows my mind! For someone a bit indecisive like myself, here are a few recommendations to get you started.

Grab a slice of deep dish pizza at Gino’s East. If you can eat more than one slice, you are a true champ in my eyes.

Spend your morning eating breakfast at Lou Mitchell’s. This diner serves donut holes while you wait in line, offers an extensive, affordable menu and passes out a taste of soft serve before you leave. You’ll feel right at home here.

One of my new blogger friends, Mattea from www.mattealinae.com

Feast on Italian goodness at Labriola. From handmade pasta to crisp salads to the largest serving of lasagna I’ve ever seen, you’ll walk (or roll) away from Labriola with a happy heart and full tummy.

Seriously delicious chicken parm from Labriola

Drink a pint and warm your insides with British fare from Elephant and Castle.

Reason #5

5. You can treat yourself to the experience of a tried and true Chicago theatrical, musical and/or athletic event. To me, there’s something so special about getting gussied up and attending a show. I recently experienced the Blue Man Group for the first time at the Briar Street Theater and all I can say is WOW! This show features three bald and blue men who will surprise and intrigue you, while simultaneously making you laugh. Warning: You may be pulled onstage to do some pretty ridiculous stunts.

On a recent trip to Chi-town, I had the absolute joy of attending the Gospel Brunch at House of Blues. From bottomless mimosas to the most extensive brunch buffet I’ve ever seen, this meal won’t disappoint. A local choir praises the Lord through gospel songs and invites the audience to partake in their joy. Seriously, don’t miss this experience.

If sports are more your thing, consider a Chicago Wolves hockey game. This professional team plays at the All State arena located 10 minutes from O’Hare airport and features a family-friendly atmosphere. Be sure to get to your seats with enough time to see the laser and fireworks show at the beginning of the game.

Reason #6

6. You can fall in love (or at least witness love) at Millennium Park. Did you even visit Chicago if you didn’t take a picture in front of the Bean?! Located at 201 East Randolph Street, this bean-shaped sculpture is the centerpiece of Millennium Park and a Chicago must see/must selfie. Grab your ice skates (or rent a pair) and hold hands with your loved ones. Skate long enough and you’ll probably see an engagement (or two). I witnessed one at the Bean and it was so fun to celebrate in this newly engaged couple’s love and excitement!

This is the whole group of influencers for this FAM trip from all over the world!

Selfie by the Bean

Reason #7

7. You can be dazzled by the Magnificent Mile’s twinkly lights. Michigan Avenue is home to the biggest and best stores for all your holiday shopping needs and wants. It’s also just as beautiful to walk down and admire the holiday decor while sipping on your favorite cuppa. During a recent trip to Chicago, I had the once in a lifetime experience of riding in the Magnificent Mile Lights Festival Parade on the Illinois Tourism bus. We spread Christmas cheer to thousands of Chicagoans while one million twinkly lights were lit around us. Magical.

Look at all of those beautiful and bundled up Chicagoans!

If you need more help planning your upcoming Chicago trip, be sure to check out the Illinois Office of Tourism’s website for more information. Feel free to comment below with your questions and I’m also happy to assist. Merry Christmas and happy holidays to you and yours!

Here’s a few other posts from bloggers that were also on this trip with me:

• Nancy from The Mama Maven: https://www.themamamaven.com/10-fun-things-to-do-with-kids-in-chicago-during-the-holiday-season/
• Samantha from The Samantha Show: https://www.thesamanthashow.com/best-things-to-do-in-chicago-during-the-holidays/

Have you ever visited Chicago during the holidays? Tell me your favorite thing to do or place to see in the comments below!

Subscribe to receive my blog posts via email here.