A Quick Magical Trip to Chicago at Christmas (Train Ride Stop)

Wondering what it’s like to visit Chicago at Christmas? Here are some magical Christmas activities in Chicago that you can’t miss.

In my opinion, there’s no better time to visit a city than at Christmastime. It’s the most magical experience, especially for a Christmas-crazed individual like myself.

I’m so excited to share my adventures in Chicago with you!

“One thing about trains: it doesn’t matter where they’re goin’. What matters is deciding to get on..”

Tom Hanks, Polar Express Conductor

Why train stops are the best for holiday adventures

Have you ever traveled cross country by train? I have and love it! If you have too, you know how fun last-minute, unexpected train stops can be. Don’t they make the journey even more exciting?

One holiday, I was headed for Los Angeles on an Amtrak train from Boston. I was excited when the conductor announced that we would be stopping for 5 hours in Chicago at Christmas!

If you were me, you’d get out and explore too, right? Uh.. yeahhh!

When is a Good Time to Visit Chicago in the Winter?

If the super crazy crowds in cities rev you up for the holidays, good for you. You’re better off visiting the middle to end of December.

However, if you’re like me and want Christmas festivities with cheaper train tickets and hotel prices as well as fewer crowds, go toward the middle/end of November. You’ll get the best of both worlds!

What is There to Do in Chicago at Christmas?

Chicago during the holidays is a winter wonderland filled with twinkling lights, festive markets, and cozy experiences, which make it one of the best cities to visit for Christmas.

Whether you’re visiting for a few hours like I did or staying for a few days or more, here are must-visit spots and Christmas activities to make your holiday season in the Windy City magical.

The Polar Express

After hopping off the train, I stood in Chicago Union Station for 10 minutes deciding how to make the most of my day trip… This was after all, a totally unplanned, spontaneous adventure and we only had 5 hours.

It wasn’t long before I started seeing people all over the station rocking their Christmas jammies… I’m like, “Clearly I didn’t get the memo!”

There were even families in twinsing onesies. Think about that awesome visual for a sec…

Then it revealed itself… The Polar Express train… live, in person, and staring right back at me. They understood the assignment. 

Evidently, it’s a whole experience at Union Station. Just like in the movie, they sing, they dance, they give you hot cocoa. The kid in me was jumping up and down. 😀

After all, you have to take a break from adulting! I do it all the time. I’m doing it now.. lol. 

So, imagine my disappointment to learn that it was SOLD OUT!! I looked like my 3 yr. old nephew when he doesn’t get his way. 🙁 #WhenAdultingSlipsAwayFromYou

At least Tom Hanks wasn’t greeting passengers himself. 😊 Then I would have really felt like I was missing out. But, if you learn that he is doing these experiences one day, you have to let me know. I’m not about to miss that.

Related: A Local’s Guide to Mount Washington Cog Railway: How to Book a Trip to New Hampshire (Top Tips + Hotels)

Guess it’s Amtrak for Me 

Until the day comes when I can get my onesie clad booty on The Polar Express, the only train this girl is riding cross country in the US is Amtrak. So not festive if you ask me. 

It was a sleeper car though which was cool… and they serve pretty decent desserts… Plus, waking up on a moving train in the middle of nowhere is pretty awesome. Even if it’s not The Polar Express.

But that cross-country train ride is for another blog! This blog is only about my time in Chicago at Christmas.

Fun Fact: The U.S. Railroad Capital is Chicago, which has more major railroads serving the city than any other place in America.

Quick Christmas Activities in Chicago

So what did I end up doing in The Windy City on my train stop? Let’s backtrack shall we!   

This is one of the best parks in the country. Not just because it’s beautiful or clean, but because of all the different things you can do and see here.

The park has a nice skating rink, places to eat, playgrounds, grassy areas for picnics and playing with your dog.

Depending on the season, they also have hundreds of annual festivals downtown and a lakefront for music, dance, film. They also have a Summer concert series. 

I recommend walking from Millenium Park down to the waterfront, which is close by.

I always enjoy checking out the different art installations scattered throughout the park… some temporary, some permanent… like Cloud Gate, that shiny, silver, bean-looking thing.

It’s a tourist trap for sure during the busier months, but still think it’s worth checking out! I happened to dodge the crowds when I went. Gotta embrace that off-season baby! I went at the beginning of the holiday season.

Oh my goodness, I’m going on about Chicago. I love talking about this city. I’ll have to make this another blog! I’ve been quite a few times. 😀 

Related: Your Guide to a Coastal Christmas in Carmel By the Sea (Where to Eat, Stay, & Play)

Ice skating here is the perfect Chicago Christmas activity and puts you right in the holiday spirit! I had such a great time here!

If you enjoy ice skating minus the crowds, late November, early December may be the time for you!  This is when I went and there was hardly anyone there.

The rink’s atmosphere is a scene from a Hallmark movie. The skyscrapers in the background… the Christmas tree! Ugghh.. Total Winter Wonderland vibes.

There are also nearby food options and hot cocoa stands. Afterward, I grabbed myself some hot cocoa, because what’s ice skating without it?

Info: Free rink admission & skating if you bring your own skates (must reserve spot). Free skating lessons Sat & Sun from 9 – 10 AM (must reserve). Skate rentals $16 – $20. Locker rentals $2. They have DJ nights.

Pro Tip: Maggie Daley Park Skating Ribbon is another great place to skate! It’s a winding path with incredible skyline views.

I know what you’re thinking, how did I squeeze all of this into a 5-hour train stop!? No, I don’t have superpowers… 😉 Well.. maybe.

Technically, I experienced Chicago at Christmas in 10 hours (Boston to LA and then back).

There are so many great foodie finds all around the city! One of my favorites is Park Grill at the skating rink. Since ice skating makes you hungry, it’s in a perfect location!

I went there for some lunch and it was very tasty. I remember thinking, I have to tell people about this place.

The drinks are also good. If you’re a Bourbon fan like me, their signature drink, The Bourbon Bramble might be right up your alley.😉  

Park Grill is a more upscale option. If you want light bites or inexpensive food, go to Park Cafe in the same building, which is their cheaper version. 

Christkindlmarket

In the land of hot cocoa-filled snowman mugs, juicy schnitzels, and pretty twinkly lights, there is an adult version of Wonderland.

It’s right here in Chicago at a very festive market called Christkindlmarket, modeled after the original Christmas markets in Germany. 

The market claims to be the most authentic Christmas market outside of Europe. Ironically, I would end up going to the real Christmas markets in Germany a few weeks later. 

I can honestly say, this one is just like the real thing with Bavarian-style restaurants, German food, and wooden stalls!

There’s hardy comfort food, sweet treats, and Christmas gifts like ornaments and painted wooden Nutcrackers.

I ended up getting 2 hot cocoas just so I could take home the mugs, they were too cute!!  

Related:

Charming Christmas Markets in Berlin, Germany

The famed artisanal food hall is loved by locals and tourists alike with over 30 different international cuisines, bars, shops, and specialty restaurants. Something for every taste and budget.

I enjoyed seeing all the different options in the French section of the market. If only my belly could fit all the yummy goodies I saw.

I stumbled upon this super cute sweet shop, Lolli & Pops with its adorable holiday display of festive treats. Let’s just say I got carried away.

UPDATE: This location is currently closed. However, Lolli & Pops has locations throughout the US and two locations within the Chicago area.

More Christmas Activities in Chicago if You’re Visiting Longer

If you have more time in Chicago at Christmas, here are some other Christmas activities you can do to make your trip magical!

Wander Through the ZooLights at Lincoln Park Zoo

This spectacular event (free on Mondays) transforms the Lincoln Park Zoo into a glowing wonderland with millions of lights, themed displays, and interactive activities like light mazes. 

Sip Cocktails at a Holiday Pop-Up Bar

For some adult fun, head to one of Chicago’s many holiday pop-up bars for some festive cocktails.

• The Lodge Tavern in River North: Cozy up in this ski-chalet-inspired setting with boozy eggnog and other holiday favorites.
• Santa Baby Bar in Wrigleyville: Over-the-top decorations and a holiday-themed menu make this spot a must.
• Sleigh Bells at Recess: An immersive holiday experience with whimsical decor and specialty drinks.

You might also like:

Best Christmas Themed Bars in the US for Festive Cocktails This Holiday

Explore the Art Institute’s Holiday Decorations

Check out the stunning Holiday Thorne Rooms at Art Institute of Chicago. They’re mini, intricately designed displays that share festive traditions from around the world. Don’t miss the iconic Lion Statues out front donning their holiday wreaths!

Take a Holiday Cruise on the Chicago River

On cruises like Chicago’s First Lady and Wendella, you can get a glimpse of the city’s iconic architecture, all decked out in holiday lights.

Shop at Local Holiday Markets

Beyond the famous Christkindlmarket, check out other festive markets:

• Randolph Street Holiday Market: Perfect for finding vintage gifts and handcrafted items.
• One of a Kind Holiday Show: Held at the Merchandise Mart, this market features unique artisan goods.
• Winterland at Gallagher Way: Next to Wrigleyfield ballpark, this winter market is fun for the whole family with, carnival rides, ice skating, food & drinks, shopping, Santa photo opps, and holiday movie showings.

See a Holiday Show

Chicago’s theater scene shines bright during the holidays. Book tickets for:

• The Nutcracker by the Joffrey Ballet: A timeless classic set in 1893 Chicago.
• A Christmas Carol at the Goodman Theatre: A heartwarming, traditional performance.
• Dr. Seuss’ How the Grinch Stole Christmas!: Perfect for families.

Indulge in Holiday Treats

Chicago is known for its foodie culture, and Christmas is no exception. Try:

• The Walnut Room: Located in Macy’s, this historic spot is the first restaurant to open in a department store and serves classic holiday meals under a 45′ tall grand Christmas tree. They also have Breakfast with Santa on select dates.
• Hot Chocolate from Mindy’s Bakery: Cozy up with decadent, homemade hot cocoa.
• Holiday Donuts from Stan’s: Limited-edition festive flavors make this a sweet stop.

Take a Holiday Lights Tour

Hop on a trolley or bus tour to see the city’s best light displays without worrying about the cold. Popular options include:

• Chicago Trolley Holiday Lights Tour: Stops at iconic spots like Lincoln Park Zoo and Michigan Avenue.
• Big Bus Holiday Tour: A hop-on, hop-off experience to explore at your own pace.

You might also like:

Add A Christmas Story House & Museum to Your Holiday Bucketlist | Cleveland, Ohio

Visit Winterland at Navy Pier

Navy Pier transforms into a winter wonderland during the holidays, complete with an indoor ice-skating rink, holiday-themed rides, and larger than life light displays. This is a perfect spot for families or a romantic evening out.

That’s a Wrap!

I hope you’ve enjoyed my recommendations for things to do into Chicago at Christmas!

Have you been to Chicago at Christmas? Would you go? Let me know in the comments below! 🙂

Thank you for your continued love and support! I wouldn’t be here if it weren’t for you.