Freestyling in Chicago: To-Dos in the Windy City
Freestyling in Chicago: To-Dos in the Windy City
If you can endure brutal, polar winters in exchange for a beautifully mild spring and summer, then Chicago might just be your vibe. Soaring skyscrapers, stunning lake views, and Lollapalooza; the city of wind might have more to offer than you may realize.
In Celebration Mode
I made my way to Chicago in early August, just after graduating college. For my girls still in university, the post- grad blues are truly no joke, but nothing a quick trip can’t fix! And Chicago happened to be the perfect prescription for the start of my first summer as a fully-fledged adult (scary, I know!) My trip was a gift from my aunt, which ended up being more than I could have ask for. Chicago was the perfect introduction to what my post grad life could look like. The world was my oyster and Chicago welcomed me with open arms. Despite having family in Chicago, I had never had the chance to visit. But, with post-graduate plans on my mind, visiting a new city was at the top of my to-do!
A Midwestern Love Affair
In true Chicagoan fashion, we celebrated by grabbing classic Chicago dogs from Portillo’s. If you know me, you know I can’t stand hot dogs. This dog, though? Yeah, I’ll need another one of those. Please and thank you. Greasy, fresh, salty, perfection. From that point on, I understood the hype. Sorry, NYC, Chicago might have something on you with the hot dogs! The love affair continued when we made our way into the heart of the city to begin our jam-packed itinerary. As we ventured into the city, I was amazed by how much of it felt like being back home in New York City. What was different, however, was the architecture and the history still marking the city. Chicago is a stunning city for this reason alone. With a river cutting right through the city towards Lake Michigan, I can’t imagine how you could not love Chicago. A cleaner, more chilled out version of New York City was exactly what I need to take a breather from constant living, working, and studying in NYC. Because I had a short itinerary, I didn’t get to explore all the nooks and crannies of the Windy City, but that just means I’ll need to visit again!
Going Lolla at Lollapalooza
How could I go to Chicago in August and not go to Lollapalooza? After spending some quality time with my aunt, it was time to party with my cousin! This day was one I’ll always cherish. For my girls who are the eldest siblings, you all know the warm and fuzziest you get when you look after a younger sibling or cousin. Nevermind that we didn’t see all the artists we planned to, nevermind that we got separated from my cousin’s friends (not that we really cared lol), nevermind that the entire festival area was a muddy messy from the morning’s downpour, what was the highlight of our day was being silly together. We took advantage of our day passes and popped into every one of Lolla’s pop-up stalls. We left Lollapalooza with free donuts, good music stuck in our heads, and even better memories! If you happen to be in Chicago during Lollapalooza, do yourself a favor and experience one of Chicago’s most popular festivals!
I’ma Touch the Sky
For my last day in Chicago, we took a ferry cruise tour of the city since it was the first sunny day of the weekend! I just loved getting to see the city with all its monuments and skyscrapers from the river. Fair warning, these cruises get HOT. The sun was beating down on us and with only humid, August breezes attempting to cool us off, this cruise tour was boiling by the end. Our cruise dropped us off at Navy Pier where we had a quick lunch and nice walk along the water. As we headed back to the heart of the city and hopped on the CTA at dusk, I realized that I had vastly underestimated Chicago. Don’t get me wrong, I visited during the summer when the weather is more palatable. I can’t say the same for winters in the Windy City. But, if you’re interested in exploring a new city that boasts attractions, classic city views, and an active nightlife scene with a Midwestern twist, Chicago is waiting for you! Another trip to the Windy City is absolutely on the books for me; stay tuned for more Chicago updates!
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