The quickie Chicago Tour of Awesome in photos

Chicago is no small city, especially after spending time in Omaha.

It’s huge. Huge.

I grew up in a suburb of Washington, DC, which basically doesn’t have any skyscrapers. Then, living in Las Vegas, the closest thing to skyscrapers we got were the resorts on The Strip.

So, coming in to Chicago and seeing those tall, lanky buildings shooting upwards towards the clouds bordered on absolutely awesome.

This isn’t my first visit to Chicago, but it is my first time as an adult.

Waking up following a good night’s sleep inside my “blanket burrito” at the Hyatt Regency is bliss. It’s the first time in days that I’ve felt well-rested.

Erica and I pack up our belongings, grab the car from valet and head to the ‘burbs to meet Katie, a dear friend of mine from my previous travels.

Then, we head back to the city via her quaint little town of Hinsdale (with a stop for a Chicago Hot Dog) and  the Metra, landing us at Union Station.

With budget in mind (we didn’t have much), Katie crafts a nearly-free tour of the Windy City.

We start by passing the Sears Tower (yes, I know that is not the name), with a walk across the Chicago River, then walk to the financial district …

… and Garrett Popcorn Shop for some of the famous popcorn.

The cheddar and caramel is the popular Chicago Mix for all you lovers of the puffy kernels wanting to try something truly “Chicago.”

Even with clouds hanging low and the chance of rain lingering, we continue on to the gorgeous grounds of the Art Institute and then Millennium Park.

Our first stop at the park is the Crown Fountain. It’s actually two glass towers that feature LED lighting and images of more than 1,000 Chicagoans’ faces. On this day, even with the lingering clouds and threat of rain, children and adults alike frolic in the shallow water.

When a stream of water comes out of the mouths of the images, children giggle with delight while we sit back and watch.

After the fountain, we stroll over to the famous Cloud Gate, a huge structure that visitors flock to daily.

We stick around Cloud Gate for a good bit, taking photos and exploring the area immediately surrounding it.

In true Winos on the Road fashion, after Cloud Gate, we head to the Fairmont Chicago for a quick glass of wine at Eno Wine Room before its time to return to Hinsdale.

On our train home, somehow we end up in the “quiet car.” Of course, keeping three giddy travelers high on the city quiet is no easy feat.


Just before the train begins its chugging, I feel a tap on my shoulder and turn around.

“This is the quiet car,” the woman behind me says sternly, pointing to the blue sticker that looks as if it was just slapped on the wall of the car yesterday.

I close my mouth, along with the other girls. For the remainder of the trip home, we silently make faces, do little dances in our seat and send each other text messages.

Katie’s mom picks us up from the depot in Hinsdale and we head back to their house, where champagne, wine and the most amazing lobster pot pie ever awaits us.

In the morning, Erica and I begin our journey to Louisville, Kentucky … the last stop before we arrive to my parents house in Maryland.

Editor’s Note: This post is a part of the #winosontheroad series. Over Yonderlust and d travels ’round went road tripping and exploring America from Colorado to Maryland in June 2012. Be sure to check out all of the posts of life on the open road.


Published by dtravelsround

Awakening the soul while traveling ... a story of being on the cusp of adulthood.

9 thoughts on “The quickie Chicago Tour of Awesome in photos

  1. I adore Chicago – that fountain is the best. Glad you got a Chicago Dog while you were there! I had no idea there was such thing as a quiet car, though, haha…sounds difficult!


    1. Those fountains were really cool! And, the Dog. Mmmmmmm. The quiet car is a new thing apparently. I think if I worked all day and wanted quiet, I would do it. But, when with friends, it just doesn’t work!


  2. I love Chicago. It’s so close to St. Louis and I am lucky enough to have a great friend there, so I have visited so many times but it never gets old! It’s gorgeous, the food is great and I just love the atmosphere. Plus, the public transit is amazeballs.


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