The quickie Chicago Tour of Awesome in photos

Written by on July 11, 2012 in Americas, Blog, Illinois - 9 Comments

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.


About the Author

Diana Edelman is a travel writer and expat currently residing in Chiang Mai, Thailand. In 2010 she quit her job in PR to go on a solo backpacking adventure and tackle her 30-Life-Crisis. After seven months abroad, journeying throughout Europe and Africa, she returned to America and relocated to Las Vegas. Following a year-long stint back in PR, she once again quit her job to follow her dreams; this time her journey took her to the elephants and Elephant Nature Park where she is involved with raising awareness about responsible elephant tourism. Recently, Diana was named a finalist in the Destinology Travel Bloggy Awards for travel writing. She has been a regular contributor to Viator and recently served as the Las Vegas contributor for and Her work has appeared in print and online, including The Huffington Post, Matador Network, Travel + Escape, Vegas Seven, World Nomads and more.

9 Comments on "The quickie Chicago Tour of Awesome in photos"

  1. Megan July 12, 2012 at 9:01 am · Reply

    It’s a bean! not cloud gate… It’s definitely a magic bean.

    • Diana July 13, 2012 at 7:32 am · Reply

      Hahaa! I know. Who knew it had a name other than that?

  2. Callie July 12, 2012 at 1:22 pm · Reply

    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!

    • Diana July 13, 2012 at 7:32 am · Reply

      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!

  3. Krista July 12, 2012 at 5:45 pm · Reply

    I haven’t been to Chicago in years!! It was so fun to relive my memories from there through your jaunt. :-)

    • Diana July 13, 2012 at 7:31 am · Reply

      I’m so glad!!

  4. Rease July 17, 2012 at 2:04 pm · Reply

    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.

    • Diana July 18, 2012 at 9:12 pm · Reply

      I wish we had the time to have bopped over to see you! Chicago really is awesome!

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