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Wondering what it’s like in Chicago at Christmas? Here are some magical Christmas activities in Chicago that you can’t miss on your quick trip there.

In my opinion, there’s no better time to go to 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 quickie train stop adventures in Chicago with you!

Why train adventures are the best?

Have you ever been on a road trip or traveled cross country by train? I have and I love it! If you have, you’ll know what I mean when I say that last-minute, unexpected adventures are the best. That’s why I always take advantage of every stop. For me, it makes the journey more fun and somehow makes it feel longer!

One holiday, I was headed for Los Angeles on an Amtrak sleeper car. Imagine my excitement when the conductor announced that we would be stopping for 5 hours in Chicago at Christmas! If you were in my position, wouldn’t you go out and explore!? 


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

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

However, if you’re like me and savor last-minute train stop adventures and want to go in November, hooray! Expect cheaper ticket and hotel prices as well as fewer crowds.

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

Polar Express Conductor

What is There to Do in Chicago at Christmas?

Always Take Breaks from Adulting! Hey, I do it all the time. I’m doing it now.. lol. 

The Polar Express

Poloar express and christmas trees in union station chicago

After hopping off the train, I stood in Chicago Union Station for 10 minutes planning what to do next. Then 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. That’s a pretty awesome visual when you think about it.  

Then it revealed itself… the train from The Polar Express… live, in person, and staring right back at me. “This makes so much more sense now.” 

I had no idea such a thing existed in real life! Evidently, it’s a whole experience you can do. Just like the hot cocoa scene in the movie, they dance, they sing, they give you cocoa, you get to wear your jammies. The kid in me was jumping up and down. 😀

So I was genuinely disappointed when I learned that it was SOLD OUT!! How many times do you get to do something like that?? I’m definitely a kid at heart and would have jumped at the chance to do that. I probably had the sad face my 3 yr. old nephew makes when he doesn’t get his way. 🙁 #WhenAdultingSlipsAwayFromYou

At least Tom Hanks wasn’t greeting passengers himself. 😊 That would have really made me upset. If you find that Tom Hanks is doing these experiences after all, oh my God, let me know! I’m not about to miss that.

If this is something you’d like to plan and do during Christmas in Chicago. Click here for more info.


The U.S. Railroad Capital is Chicago with more major railroads serving the city than any other place in America.

Guess it’s Amtrak for Me 

Until the day comes when I can get my booty on The Polar Express, the only train this girl is going to be riding is The Amtrak. So not very festive if you ask me. 

It was a sleeper car though… fun… and it serves pretty good desserts… yummy… and 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! Today, I’m sharing my time in Chicago at Christmas.

Pro Tip: I made the mistake of wearing jeans for the train ride and regretted it. I recommend wearing something comfy like leggings or for the long train ride like a stretchy track suit.. adidas makes some good ones.

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Quick Christmas Activities in Chicago

chicago high rises

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

chicago millennium park

I think this is honestly my favorite park. Not just because it’s classy and clean, but because of all the different things you can do here. It’s a lovely walk too. 😉  

The park also has a nice skating rink, places to eat, playgrounds, grassy areas for picnics. Depending on the season, they have hundreds of annual festivals downtown and lakefront for music, dance, film, and food. They also have a Summer concert series

It was very quiet when I was at the park that day.


“Urbs in horto” became Chicago’s motto in the 1830s. It means, “city in a garden” and alludes to the city’s impressive and historic park district. With over 8,800 acres of green space and 600 parks; the Chicago Park District is the largest municipal park manager in the nation.

Source: Choose Chicago

I always enjoy checking out the different art exhibitions scattered throughout the park, some temporary, some permanent installations 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.

Real Girl Review Tip

Want to learn about the history of Chicago and be introduced to some great spots?

Check out Sherpa Tours!


There are over 500 public works of art displayed around the city as part of Chicago’s Public Art Program. These works include installations by Picasso, Chagall, Miro, and Calder.

Source: Choose Chicago

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. 😀 

At Millennium Park, there’s McCormick Tribune Ice Skating Rink. When I saw it, I had to go! If you enjoy ice skating minus the crowds, late November, early December may be the time for you!  This is when I went.

What a refreshing atmosphere! The skyscrapers in the background… the Christmas tree! Ugghh.. what I love about cities at Christmastime.

Ice skating just seemed like the perfect Chicago Christmas activity. It put me in the holiday spirit!

I had such a great time here! The rink’s atmosphere is lovely & conveniently located in Millennium Park. Nearby food options for every budget. Even a hot cocoa stand. 

Afterward, I grabbed myself some hot cocoa, because what’s ice skating without it?

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.

But, I experienced Chicago at Christmastime on the way to LA and then on the way back to Boston. The train made stops in Chicago both ways.

Free rink admission. Skate rentals $13 – $15. Free skating lesson 1 hr. before the rink opens! They have DJ nights.

Christmas Markets in Berlin

Have you experienced the Christmas markets in Berlin, Germany? The markest in Europe is like no other. They are magical, full of delicious foods and beautiful ornaments. See why you should plan a trip to the Christmas Markets in Berlin.

There is 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 was impressed. I remember thinking, I have to tell people about this place.

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

It was conveniently located, the food and drinks were delicious. The grill is the more upscale option, the cafe is the budget-friendly option, good if you just want a snack. 

If you want light bites or inexpensive food, they also have Park Cafe in the same building which is their cheaper version. 

Christkindlmarket  (Christmas Market)

3 star element

In the land of hot cocoa-filled snowman mugs, juicy schnitzels, and pretty twinkly lights, there is the adult version of Wonderland. It’s a very festive place called Christkindlmarket. 

After the disappointment of not being able to ride the sold-out Polar Express train, I walked down the street and arrived here. And just like that, the excited kid in me came out again.  

A little taste of the Christmas markets in Europe. Hardy comfort food, sweet treats, and Christmas gifts like ornaments and painted wooden Nutcrackers.

Germany has world-famous Christmas markets which this one sort of reminded me of. Ironically, I would be going to the real Christmas markets in Germany a few weeks later for Christmas. 

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

Do you have a Chronic Illness and Want to Travel?

Just because you have a chronic illness, doesn’t mean you can’t travel!
In my blog, “Traveling with Chronic Illnesses”, I share some tips that have helped me with my Lupus while traveling. I also give a peek inside the handy dandy sanitization kit that I bring with me on every trip for those with autoimmune conditions!

The famed artisanal food hall that’s loved by locals and tourists alike. It has 30+ different cuisines, bars, shops, and specialty restaurants. Something for every taste &and budget.

This market is great! Inside is a famed food hall with a nice selection of international cuisine, bars, specialty restaurants, and shops. What I love about the market is that it’s so diverse with something for every taste and budget. 

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

I stumbled upon this super cute place for the first time when going into Metra Market, a great place for food options and shopping btw. Lolli & Pops caught my eye with its adorable holiday display of festive treats.

I ended up getting a bunch of sweets, devoured most of them on the train back to Boston but managed to save a box of truffles for family. 

I’m glad I came here when I did because they’re no longer in Chicago. They do have locations all over. Check to see if there is one near you here.

That’s a Wrap!

I hope you’ve enjoyed reading about my quick train trip to Chicago at Christmas, and got some inspiration for your own trip!

Have you been to Chicago at Christmas? Which is one of your favorite Chicago Christmas activities? What are you looking forward to?

illustration of geeves traveling with pink suitcase and blue outfit

If you enjoyed this blog, I’d love it if you left a comment below. Thank you for your continued love and support! I wouldn’t be here if it weren’t for you.

If you enjoyed this post, you might also like:

20 Helpful Tips for Traveling with a Chronic Illness

A Real Girl’s Christmas Market Adventures in Berlin

Best Christmas Themed Bars for Festive Cocktails This Holiday

A Colorful Adventure in New York City


  1. Chicago in winter? November is my go-to! Cheaper tickets, fewer crowds. Missed the Polar Express, but Millennium Park’s skating rink and Christkindlmarket made up for it. Next time, wearing leggings for that Amtrak ride haha!

  2. So far, I’ve only had a short layover at the airport in Chicago. But, I’ve got to go there and try some real Chicago deep dish pizza.

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