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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 and I’m so excited to share my quickie train stop adventures in Chicago with you!

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 less crowds.

Train Stop Adventures Are the Best!

Have you ever been on a roadtrip or traveled cross country by train? I have and I love it! If you have too, 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 LA on an Amtrak sleeper car. Imagine my excitement when the conductor announced that we would be stopping for 5 hours in Chicago… at Christmastime! If you were in my position, wouldn’t you go out and explore!? Ayuhhh… 

“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. 

After hopping off the train, I stood in 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.” 

The Polar Express Train, Chicago Union Station

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

If only my Amtrak train was The Polar Express

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..


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 Chicago adventures.. at Christmastime! 

My Winter Adventures in the Windy City

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

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


“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.

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

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

When I went, the park was very quiet.

Pritzker Pavilliion’s speakers are faster than the speed of sound!

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. 😀 


In 1688, Chicago was first recorded as “Chigagou”, an Algonquian word that means “onion field.”

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 Christkindlmarkt.

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.  

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!!  

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 holiday activity. It put me in the holiday spirit!

Afterward, 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 super powers… 😉 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.

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 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.😉  

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

Metra Market

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 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’m glad I came here when I did because they’re no longer in Chicago. They do have locations all over though.

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. 

And now, for my favorite part…

Real Girl Reviews

The Good, the Bad, & the Ugly

Ice Skating, McCormick Tribute Plaza

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. 

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

Millennium Park & Cloud Gate

1 of my favorite parks. Great views of city. Lots of art installations. Seasonal park events. Cool bridge takes you to other lakeside of city. Great photo opps. Food options closeby. Skating rink. Family & Pet friendly. A must do!

Christkindl Market

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

Missed the entertainment factor for me. No shows or rides. Mostly for foodies. 

But it was cute. I got hot cocoa & kept my mugs as a souvenir!

Park Grill & Cafe 

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

Lolli & Pops

This place is inside Metra Market. The holiday treats selection was so fun & yummy! The staff was also very friendly. Unfortunately, they're not in Chi-Town anymore.

Metra Market

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

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

My Sam Edelman All Nighter Heels

I love Sam Edelman heels and boots for their quality and they're so cute!

I brought my black leather booties on this trip. Have had them for many years and they've lasted me through long nights walking through cities all day. One trip, I roamed NYC until the next morning. They earned a nickname. I call them my "all nighter" heels.

Plan your trip!

Get My Chicago Google Maps Itinerary Here

You can also copy, print, share, or download it!

Do you enjoy the whimsical sights of cities over the holidays like I do?! If so, what was the last city you went to? What did you do there?

I love hearing from my readers! Feel free to comment below and let me know if you enjoyed my post. 

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Real Girl Review strongly values truth and strives for accuracy. If you read something that doesn’t sound right, feel free to contact me and I will investigate the facts and make changes as I deem necessary. Posts are updated regularly.

Always keep it real…

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