Chicago Flip!

Exciting Adventures Below!

Chicago- Wanderlust + History + Adventure!

Assignment III- GUIDE

I can remember when the plane crossed Lake Michigan, the water was so blue. Not murky blue like the Atlantic, or deep blue like the Pacific, but a pale, almost aqua blue, and it was beautiful, to this day, it is some of the bluest water I’ve ever seen. I knew from that moment that Chicago would be different. My family and I lived there for almost 5 years, and it was fantastic. Chicago is known as the Second City for several reasons, each reason reflecting its history and growth. In 1871, (Gunderson, 2023) the Great Chicago Fire destroyed much of the city, and instead of abandoning it, the residents rebuilt it. They created a new, stronger city, and their pride led to the nickname of “The Second City” because it was essentially built twice. For many years, Chicago was the second most populous city in the United States, after New York City and over time, the nickname has evolved to reflect Chicago’s spirit and determination. It has become a beloved part of its identity.  So why would a traveler consider Chicago a place of wanderlust? Well, first, they must have the desire to explore and experience a city that is not flashy like Vegas or NY, but also not as glitzy as Los Angeles or Miami. It’s a city that requires curiosity about its culture, architecture, and attractions. These will come in handy for those willing to explore and contribute to the travel journey.

The Sky Deck offers almost picture-like views of the city from the Willis Tower (formerly known as the Sears Tower). It’s a must-do for those wanting to experience the layout of the city and its skyline. While I noticed the blue water landing in Chicago, I also noticed it’s completely flat. Pennsylvania is mountainous, and after about 6 exits on  I-76, your ears start to pop based on the altitude going to Pittsburgh. Not so for Chicago, it’s completely flat, you can see the entire city and its surrounding counties on a clear day. And this flat landscape allows for a beautiful skyline day or night. The lake (Michigan) offers a beach as well as boat excursions; the boats range in size, but they can show you all the sights, especially around the architectural phenomenon on the river, and get you a great tour guide; you are in for a treat. Just by cruising on the Chicago River, a river that turns green for St Patrick’s Day by the way you can learn a ton about the city.

Chicago, like most big cities, boasts all the sports teams, and just like other big cities, it even have two baseball teams with a unique history. The White Sox play on the Southside of the city and are pretty much supported and heralded for their “working class” roots, emphasizing speed and agility, reflecting the gritty spirit of the community (Sullivan, 2025). The Chicago Cubs have long been associated with the more affluent North Side. The geographic divide between the teams symbolized broader cultural differences within Chicago, and it was one of the first things shared with my family when we moved in. Our friends let us know we had to be “Sox” fans, no discussion. But just like other sports towns, they have hockey, football, and of course basketball. I mean who can forget the 90’s when the Chicago Bulls dominated the game with Michael Jordan? Most natives will start talking about it as soon as you mention any sport from another area, and they are fierce about the dominance the Bulls had. But hey, who could blame them? It was one heck of a run.

As far as iconic landmarks and sites? Millennium Park is known for its architecture and public art exhibitions; many times, I would meet my mom in town with my big brother, and we would eat at the cafés on State Street and walk through the art displays. There are both unknown and well-known artists showcasing their work, which makes the experience so much better. There is a “Bean” in Millennium Park. The Bean is a public sculpture that was created by Indian-born British artist Anish Kapoor and was unveiled in 2006. The Bean (shaped like a kidney bean) is made from steel plates to give it a polished finish. (Reynolds, 2024) It is an interactive experience and distorts your reflection like an old carnival funhouse. I would not miss it. There is the Magnificent Mile, a historic stretch of Michigan Avenue famous for the upscale and expensive shopping, dining, and architectural attractions. The Navy Pier, where the Centennial Wheel, aka Ferris wheel, is for the “old folk” or couples, but also where the summer fireworks are displayed. There are so many museums and parks, there is even a botanical garden called the Garfield Park Conservatory, where some of the most beautiful plants and flowers I have ever seen.

The food of Chicago needs its paper, but I will try my best to give a bit of insight. Being from a city like Philadelphia, you automatically feel like no other city can match your city’s brand of taste. I mean, Philly has the food. But Chicago was special because it was unexpected. Sure, you hear about their famous deep-dish pizza or their hot dogs (mustard only, no ketchup, tomatoes, and peppers) on a seeded bun- interesting to see but so good! The Garrett popcorn, Harold’s Chicken, the Italian sandwiches, or even the famous rainbow cone, which features a cone piled with different flavors of ice cream and sherbet. But what was unexpected was three franchise restaurants I had never heard of that sold me 100% in Chicago, and I miss them often. (1) Portillos has hot dogs, burgers, milkshakes from scratch, grilled chicken sandwiches on croissants, and chocolate cake! Now, all those may seem like normal foods, but they are all made Chicago style, and they are delicious! Next is Culvers- again American fare like onion rings, chicken tenders, fried shrimp in a basket, but they also had real soft serve ice cream cones. You can get all the food pretty late too (they stay open until midnight in the summer), unlike McDonald's, which always says the machine is broken down. Last was Weismann, a full-service ice cream parlor, some of the best floats, cones (waffle/regular), and shakes I have ever tasted. They are associated with an actual dairy farm in the county I lived in, so the taste was incredible. The food of Chicago is deeply ingrained in the city’s culture, so the spices, the flavors, and the authority were top tier. There is so much more I could share, but for now, just knowing this city is alive with all the heart and soul you would ever need to feel welcome beyond a quick weekend, if you are a city person like me, Chicago is a great place to call home.