Bold architecture? Delectable food? Astonishing art? Chicago, one of the largest cities in the United States, has it all. I was fortunate enough to visit the Windy City last year over Labor Day. I had been looking for a chance to explore this destination, and when I saw flights for less than $100 round-trip (on a holiday weekend, no less) I took it. During my stay, my friends Shawna and Shelly were kind enough to let me stay at their apartment that they just recently moved into. Together, we couldn’t wait to get a taste of their new home!

Although I was only there for a short time, I instantly was captivated by Chicago’s beautiful skyscrapers, jutting shorelines, and charming city vibes. My first experience upon landing at the O’Hare airport was taking the rapid transit system, more commonly referred to as the “L.”  This elevated rail system is easy to use and conveniently connects all of Chicago.

We started our first full day with a short run on Lakefront trail. This eighteen mile path stretches along Lake Michigan and is popular for walking and cycling. There were countless others taking advantage of the still-warm September. We were rewarded with a peaceful view of the sun reflecting off the water and the calming sound of boats bobbing in the harbor as the waves came in.  On our way back, we passed Wrigley Field. While I didn’t catch a game here, I could still feel the atmosphere from outside this legendary stadium. There were proud fans decked out in the classic red and blue colors and all types of Cubs merchandise everywhere I looked.

Later, we took the L downtown. I had made it my mission to check the Skydeck in the Willis Tower (also referred to as Sears Tower) off my bucket list. It arguably has one of the most impressive views, in close competition with the Chicago 360 experience at the John Hancock Center. We tried to arrive before lunch to beat the crowd, but were still greeted with long lines. After stepping foot off the elevator, it was clearly worth the wait.  This attraction, on the 103rd floor of the tower, boasts views extending over state lines and has four clear observation boxes with glass floors that make for the best, but slightly terrifying, Instagram photos.

It’s no secret that Chicago is known for its food, particularly hot dogs and deep dish pizza. It’s also no secret that this is what I was looking forward to experiencing the most. We’d received a tip to check out Portillo’s, a local chain known for Chicago-style dogs. Although we weren’t keen on the idea of visiting a chain, we were pleasantly surprised upon entering the restaurant. It had a very retro vibe and large menu. We noticed that their chocolate cake seemed to be quite popular as well. Not being one to ever pass up cake, I ordered both and can vouch for those menu items and this place. The Chicago-style hot dog is often topped with mustard, relish, a pickle spear, tomatoes, onions, and peppers on a poppy seed bun. It was messy, but mouth-watering good, and the chocolate cake nearly melted in my mouth. Delicious, affordable, and remarkably decorated, I left more than satisfied with my experience.  

After our lunch, we strolled along the Riverwalk. Many people were relaxing at diners by the river or on a stroll from their lunch break. The vibrant colors of the flowers, along with the bridges and the bright hues of the water made me wish I worked in Chicago and could take my lunch breaks here every day. After more walking downtown, we caught the L back to the Lakeview neighborhood. While we unwinded from a long day of walking, we enjoyed beer from Revolution Brewing Co.

Before I had left for my trip, I’d done my research online and asked several friends about the best place to get Chicago’s famous deep-dish pizza. The winner was Lou Malnati’s, which we chose for dinner that evening. I had built this moment up in my mind, and wasn’t sure what to expect when I took that first bite, but let me tell you, this exceeded any expectation. My taste buds were singing! The sauce was the perfect blend of tangy and sweet, the fresh mozzarella cheese was delightfully gooey and the crust was buttery and baked to perfection. This heavenly entrée is a must.

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The next morning, fully rested, we set out to conquer more sights. First was wandering through Lincoln Park and the zoo. With or without kids, this is an incredible place to visit, and best of all, it is free and open to the public! We stopped at one of Chicago’s many beaches, Oak Street Beach, to sink our toes in the sand and cool off in Lake Michigan before reaching Navy Pier, where Lobsterfest was taking place. However, the crowds were no match for the spectacular views of this landmark. The contrast of the beautiful beaches with the massive skyscrapers in the background left me breathless. I truly picked a great weekend to visit, for as we headed further south to Millennium Park, we caught a captivating performance from the jazz festival. After enjoying the soulful yet electrifying music, we moved on to admire the many sculptures and mesmerizing art. Among them, and no doubt one of the most popular sculptures in the city, was Cloud Gate, or “The Bean” as it is often called. I watched the sunset near the Buckingham Fountain and admired the light dancing off the buildings, in awe of the perfect ending to the perfect weekend.

So there you have it: spending less than seventy-two hours in a city may not seem like much, but it was more than enough to give me a taste of Chicago and leave me wanting more. Although there is plenty more ground to cover whenever I visit again, this little getaway was a great introduction to the Windy City.


Follow more of Kara's traveling adventures by checking out her blog: From This Side of the Sun.



Kara Knickerbocker

Kara Knickerbocker is a writer and world wanderer eating her way through her travels. She is the author of Next to Everything that is Breakable (Finishing Line Press, 2017).