The Windy City


On my first solo trip, I packed a carry on filled with a thin coat, a sweater, and jeans and headed off to Chicago. When I got there, I soon realized why the tickets were so cheap. First of all, it was mid-November. And they weren’t kidding when they named it the Windy City. It was constantly windy. The cold bit at my skin through my thin Oklahoma winter coat. You can see everyone’s hair whipping about in the picture above. I basically ran everywhere to keep warm.

Chicago style in Grant Park

One of the things that struck me almost immediately about solo traveling is that I could go anywhere I wanted, do anything I wanted whenever I choose; however, that also meant that I had to constantly make decisions with little to no information about the city. That left me with the GPS on my phone and my intuition. This would later become my preferred method of exploring a new place.

My intuition led me to eating a Chicago style hot dog in Grant Park while I walked along Lake Michigan. By the way, have you guys had a Chicago style hot dog? Um, hi, they give you a whole pickle ON the dog. I don’t know why it took me 23 years to try this. Don’t make the same mistake I did, my friends. I think they have them at Sonic for those of you who can’t try the real thing.


I also walked around ritzy neighborhoods in Lincoln park for several hours. By walking I mean running. The streets were littered with freshly fallen gold and amber leaves. I found a small Thai place that served delicious curry. I spent hours in that restaurant reading and coming up with ideas for my next venture.


One morning, I took refuge from the wind at the Chicago Museum of History. Who doesn’t love a good museum? I remember being in awe of the city’s rich history. There were several times in history when the people of Chicago united to fight oppression and to help their fellow neighbors. I’m sure it was the pretty side of history, but it was very inspiring. This photograph was taken by a photographer in the 1960’s. She took snapshots of the people she encountered on the streets of Chicago. I find this photo particularly captivating. I would love to have spoken with this man to hear the story behind the expression on his face.


Rookie mistake #5235 on this trip: I didn’t plan on the sun setting at 4:30 PM. I was wandering around the side streets of Chicago when it suddenly began growing dark. And cold. I did not want to find myself in a bad part of town after dark, so I grabbed a cab to take me back to my hotel. I did end up in a bad part of town after dark on another night, but that’s a story for another post.

2 thoughts on “The Windy City

  1. actually, this is gmom I loved your story and you did a great job describing your travels.

    I found Chicago to be the same. When we had the Pepperidge Farm franchise up there, I got stuck parked outside on the street outside the bakery and one of the workers came and moved my car inside so I would not be attempting to enter the car after dark. The neighborhood was much different after dark than during the daytime. Your great grandmother and I waded in the lake in the summertime and the water was still freezing.

    1. Mae Goes West

      What a fun memory! I learned a lot on this trip, like how to layer my entire suitcase full of clothes to keep warm. Well, I learned that didn’t work anyways 🙂

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