Wandering Through Chicago

Chicago Night

I don’t know what I was thinking when I accepted an invitation to visit Chicago at “month end” (ie. the beginning of October. Accounting is weird like that). It’s the worst time to be away from work when you’re a bookkeeper, but I decided to ignore the anxiety brewing in my chest anyway; I submitted a time off request, booked a round-trip train ticket for $54 (how can you beat that price?!), and tried to push the thought of having to complete three days worth of work in 1.5 days out of my mind.


The day of departure, I tried reading Agatha Christie’s Murder on the Orient Express (because what could be more appropriate?), but I soon found myself distracted by Michigan landscape. The scenery is so pretty here; I just wish we had the economy to match. It could be worse though. I could live in Indiana. *shudders* TO BE FAIR! The train goes through Michigan City, Gary, and East Chicago. With its ugly steel mills, sprawling freight yards, and charming coal and natural gas power plant over-looking Lake Michigan, I know it is not Indiana’s finest. Also, Children of the Corn. I digress! After several delays due to interfering freighter traffic, I made it to Chicago nearly an hour and a half later than I intended.

O, Chicago! The only big city that I like that I’ve visited. I should probably take a moment to explain how my view of “big cities” is skewed. The city I currently live in has a population of about 115,000 people. That is a lot of people to someone who lived in a city of 33,000 people prior. The people here are abrasive. The surface streets are too narrow and congested with traffic that has little regard for turn signals and traffic lights. I look forward to waking up and going to the grocery store by 7:00AM because any later and the crowds of aimless and lollygagging shoppers is unbearable; I miss the quiet aisles of Polly’s Country Market even though their Poptart selection isn’t nearly as varied as Meijer’s. That being said, I really, really like Chicago even though it’s hard to find a quiet spot, people drive like maniacs, and it’s hard to walk down the sidewalk without walking into a plume of cigarette smoke.

The Food

One of the best things about Chicago is the food. It’s some how the perfect blend of culturally diverse cuisines and hearty midwest meals. Sadly, I didn’t snap any photographs of the tasty dishes, but next time you’re in Chicago, I recommend these places:

  1. Giordano’s for amazing Chicago-style deep dish pizza and their amazing house salad (lemony, peppery, and fresh!)
  2. Cafecito for Cuban-style sammiches and coffee. I recommend the Palomillo sandwich (which I still dream about).
  3. Yolk. for delicious breakfast. It’s hard to go wrong with eggs, when a restaurant is called “Yolk”! Definitely try their Eggs Benedict.
  4. Eleven City Diner for dessert. It’s perfectly reasonable to go to Eleven City for a slice of their homemade Red Velvet Cake. Even if you’re one of those people who are like, “I don’t understand why Red Velvet Cake is a big deal”, you will after eating a slice at Eleven City Diner. (Runner up: 11 City French Toast– fresh-baked challah french toast topped with strawberries, bananas, and toasted coconut). Plus, if you sit at the bar, you can admire a photograph of Tom Waits.


The Sights

  1. Lake Michigan. I’m from Michigan, so I think our side of the lake is superior (and more natural), but seeing a rigid city skyline juxtaposed next to natural waves is nonetheless stunning. And there is no shortage of views of the shoreline in downtown Chicago. I could see it from my hotel room. I could see it while wandering around Buckingham Fountain. I could see it from Navy Pier (which I would like to visit during the summertime)
  2. Field Museum. It’s no secret that I’m a massive nerd. When I heard I was going to visit the Field Museum, I nearly did backflips. I spent the entire afternoon wandering through the deceptively massive museum. I saw REAL MUMMIES in the ancient Egypt exhibit. I watched scientists work on fossils at the McDonald’s Fossil Preparation. I saw countless stuffed animals (which was actually kind of sad), but I did get to see a mammoth and a mastodon, and that was amazing! I also took a tour of America’s ancient history (pre-colonialism). AND! I finally got to meet Sue, the T-rex. Believe it or not, my six hours at the museum only got me through 3 exhibits. I so desperately want to go back to see the exhibits on China and the Vikings.
  3. Art Institute of Chicago. I didn’t visit the art museum during my last Chicago visit, but I meandered through it a few years ago, and it’s kind of mind-blowing. I contemplated visiting the museum my last day in Chicago when I was by myself, but decided against it (for reasons I’ll go in to in just a moment). This is another museum that is deceptively massive. Highlights include seeing Andy Warhol’s Mao as well as a collection of arms and armor from the Medieval and Renaissance periods. This is another museum that I really want to visit again, especially now that I’ve been reading up on “art appreciation”.
  4. Millennium Park. You can check out the Cloud Gate (or “the Bean”), but visit on a weekday if you can because it’s crammed with people on the weekend. Honestly, downtown Chicago is one gigantic sculpture garden. You can pretty much wander up and down random streets and see amazing artwork. In fact, I would encourage that because everyone else is so enamored by “the bean”.

The Best for Last

I spent my last day in Chicago alone, and it was a pretty incredible experience. Yes! It is possible to be alone in a city of over two million people!

My goal was to get ridiculously lost and somehow manage to make it to my train in time. I found this lovely neighborhood that was somehow so quiet despite being surrounded by busy streets; perhaps towering skyscrapers blocked all of the noise. Next to the neighborhood was a park with sprawling green grass, where friends gathered with their puppies for a picnic. There was children playing on a playground that was canopied with trees. And there was a pathway with the occasional bench and modern-styled fountains, so all you could hear was the sound of bubbling brooks. All I could think about was how perfect this spot would be to sprawl out and read.

Plus, corporations were closed and people were off doing touristy things in other parts of the city, which meant I could stand around and gape at amazing architecture and buildings that brushed the sky without being jostled by people in a hurry. I was in awe.


Even though I was just there a month ago, I already want to go back. There are many museums and exhibits that my nerdy soul desires to stroll through, and there are so many pictures of food that I want to take without shame. I sort of want to visit during the holiday season (ie. Christmastime) because I really would love to see parts of the city all lit up…Do they light the city up for the holidays?

Have you ever visited Chicago? Where are some of your favorite places to visit in there?

Published by

Jackie A.

Michigander. Bookkeeper by day; blogger by night. Some of my favorite things include: travel, photography, video games, sweater-weather, reading, and tea. The Harry Potter books are my favorite, and I can never have too much peppermint tea.

3 thoughts on “Wandering Through Chicago”

  1. If I ever visit Chicago I’ll make sure to go to the places you mentioned. Millenium Park is gorgeous, the Art Institute sounds amazing (seeing as I’m quite the art nerd), and the Field Museum is just..
    Real mummies? A yes from me haha!


  2. As someone who lived in Chicago for the majority of my life, I am so glad to see you enjoyed it! Lake Michigan, the Field Museum and The Art Institute were some of my favorite sights when I lived there, so it’s great that you got the opportunity to see them. 🙂 Thanks for sharing your experience and, as always, fabulous recap! ♥


  3. Ooh, this is really cool! I think I was in Chicago once … for transit. XD XD XD But it’s funny that I should read this post because we’re studying a short story in Chinese — ‘Death in Chicago’ by Pai Hsien-yung? It’s about overturning all the Chinese idealisations of the West, but I have to say, pizza sounds fantastic idealised or not. Lake Michigan remains somewhat creepy to me, even though the pictures are super pretty!


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