One Day in Chicago: Winter Wonderland in the Windy City

One Day in Chicago: First Impressions

Chicago was both exactly what I expected and completely different than I imagined.

Each house and structure is a gorgeous window into an industrial past.

I always pictured Chicago like I’ve seen and heard it portrayed– a cool, shifty, dusty place. However, I didn’t ACTUALLY expect it to be just that.

We were only in Chicago for nineteen hours, as this weekend was meant as an experiment in standby flying.

I had just started a job as a customer service agent with an airline. I was a bright-eyed recent college grad– when you dangle flight benefits in front of me, I’m gonna take ’em!

Our flight there was super smooth– plenty of open seats, not too many standbys. It was an uneventful flight. Wyatt and I were seated in the bulkhead, right behind first class, and the excessive leg room was a nice change.

One Day in Chicago: This Hotdog is a Wiener

We landed around 1:00 pm and started our crazy, hectic, wonderful day in the Windy City. We were literally researching where to get the best Chicago-style hot dog as we walked out of the terminal.

First, we had to get to the hostel 15 miles away with a brief stop for lunch. This may seem like an easy task to most, but I grew up without public transportation. I did not possess the skill (or art) of navigating big cities.

It doesn’t help that I’m terrible with directions to begin with. The hardest part about today’s commute was finding the train station.

Looking back, signs through the airport pretty clearly told us where to go, but hey, hindsight’s 20/20.

Finally, we made it to downtown Chicago and got ourselves a dog from the “Wiener’s Circle.”

We chose this particular stand because of its proximity to our hostel, but I can’t lie– I would have chosen it anyway. I may be a grown adult woman, but come on, some things are just funny.

The hot dog was delicious– perfectly charred and equally tender. The atmosphere was better. This was a humorous and perfect first *taste* of the city.

One Day in Chicago: Snow Day at Millennium Park

Of course we had to visit the Bean, which (much to my surprise) is officially labeled “Cloud Gate.”

It is an interesting, fun, and beautiful piece of art– one of many artistic jewels you’ll come across while wandering around the city.

On our walk to Millennium Park, it started snowing heavily. It was so surreal– catching snowflakes on our tongues under towering, decades-old buildings.

I’m sure I would have enjoyed Cloud Gate on a bright sunny day, but it seemed all the more magical cloaked in a blanket of snow.

We filled another snowy couple of hours walking around Grant Park and Lake Michigan and admiring the architecture. It was peculiar to have most of the park to ourselves in a city of over 2.5 million.

One Day in Chicago: Pizzeria Pig-Out

When we were finally cold and hungry enough, we made our way to the first pizza place we’d visit that night. (That is, after we kind of accidentally snuck into the aquarium… I plead the 5th.)

The line at Lou Malnati’s was long, but oh was it worth the wait! We devoured the juicy feast.

A little girl at the table next to us poignantly remarked, “Chicago– the place where pizza isn’t a finger food.” She may have a marketing career in her future.

After chowing down on two personal-size pizzas, Wyatt and I looked at each other. We were both slightly ashamed of what our tipsy, curious minds were thinking. “So… want to go to another pizza place?”

We wiped from our faces the delicious sauce of one glorious deep dish pizza and proceeded to walk four blocks in search of another.

Gino’s East treated us to an unreal buffalo chicken pie. Thinking about it still makes my mouth water.

Inside information from a friend who hails from Chicago led us to two different pizzerias that night.

Wyatt and I argued about which was the best, Lou Malnati’s or Gino’s East, finally agreeing that both were fantastic. We’d just have to try them again someday before declaring a winner.

I vowed not to tell of my fattening, carb-loaded, greasy evening as I thought it might damage my reputation as a health educator (the title granted to me by my college degree).

But I’ve always preached moderation instead of restriction, and traveling to a place is incomplete without indulging in the city’s delicacies. When you’re only in that city for 19 hours, prepare to stuff your face.

One Day in Chicago: Hostel Hooligans

Our day in the Windy City lasted well into the night. We spent it playing billiards with an Indy bartender and a Norwegian groomsman still in his tux.

We shared Old Styles. (NOT a Chicagoan beer, much to our surprise… still felt a little Shameless.)

The soundtrack of our one and only night in Chicago consisted of the drunken Norwegian’s awkward imitations of the sounds girls made during his sexual romp through Japan. Ah, hostels.

One Day in Chicago: Reflections

I’ve never felt like I completely didn’t know who I was, but as any twenty-something will tell you, there’s always a feeling of MORE.

The misconception that you’ll “find yourself” in college leaves you feeling confused and questioning whether you “know yourself” when you graduate.

I feel like traveling will help me “find myself” more than 6 hours a day in a classroom ever could.

How can you know who you are before you realize you’ve accidentally walked half a mile in the wrong direction while it’s dumping snow in an unfamiliar city?

Go with the flow. I’ve always admired the sentiment. Traveling (and life in general) is much more enjoyable when you embrace that.

You may not make that train, the museum might be closed when you arrive, and your feet will hurt. But the only thing stopping you from having a good time is yourself.

It’s snowing and you won’t be able to see the view from the skyscraper you were going to climb? Build a snowman in the park.

Tired of walking? Take a coffee break in a quaint cafe.

As I sat on the plane home, sipping white wine at ten in the morning, reading a good book, I could not help but feel content.

Looking Forward to the Future

As Elizabeth Gilbert so eloquently states in Eat Pray Love, “You were given life; it is your duty (and also your entitlement as a human being) to find something beautiful within life, no matter how slight.”

A scene in the book described a group of friends each explaining what they’re thankful for. I am grateful that I decided to go with my heart, my hopelessly wanderlust-filled heart.

I took a risk in accepting a part-time job for an airline when I already had a full-time position.

I couldn’t be happier with my choice.

My family didn’t understand. “You won’t even have time to travel.” “When will you sleep?” “That has nothing to do with the major you just earned.”

But this is what I want to do right now– work hard and long and play harder and further away. And who’s to say this isn’t what I want to do for the rest of my life?

As long as I’m happy, who cares if I make the most money I could or if I use my major in every job I have?

The answer is sad: a lot of people care– people I love so dearly and people whose opinions I cherish.

I’m learning that the only opinion I really need to worry about is my own.

I do not want to look back at my life and think, “If only.”

They don’t understand right now, but maybe when they see how happy I am living an unconventional, exhausting, exhilarating life...

Don’t worry about it. They might get it, they may never. I only need to worry about myself and what brings ME happiness.

You could call that selfishness; I call it empowerment. I’ve finally taken the reins of my own life and decided I’m going to LIVE.

Our one day in Chicago was the perfect way to kick off my travel journey!