Traveling to a big city never fails to make me feel inadequate. The sun’s going down, and amateur blues players begin to spark up with saxophonist tunes. Gothic-like architectural wonders seem to reach out to the hazy October sky, while ambitious shoppers dolled up in tweed ensembles quickly exit the stage of Michigan Avenue. Just looking up at the skyscrapers of Chicago’s downtown metropolis, I can’t help but imagine the small speck of paint I represent in the grand picture.

It’s my second time here, and with much of the typical touristy venturing out of the way from my first trip, I’m aiming to experience something a bit more local. Instead of devoting mealtime to deep-dish pizza and acting like a child photographer at the Bean, I’ve decided to head uptown to check out one of Chicago’s hidden gems.

The main destination, while a lengthy distance from the heart of downtown, is an area my inner hipster was begging me to go. Titled the 4th hippest spot in the U.S., Wicker Park is the “younger” part of town; quite essentially, the trendy hangout of well-dressed 20 somethings. It seemed to be a place in constant motion, as nonstop crowds shuffled in and out of eccentric cafes and restaurants. Some people I passed howled at the shenanigans of the night before., while others multitasked, walking with their nose in a book. This was the diverse range of people that made Wicker Park so intriguing.

If you’re familiar with Toronto’s downtown area, this would be your rugged version of Liberty Village. Basically what I’m saying is that within Chicago’s confinement, Wicker Park is nothing short of refreshing.


My afternoon there consisted of fish tacos and cinnamon almond milk at Bigstar’s—an indie-inspired Mexican snack patio covered with playful yellow chairs and twinkling lights. Sitting back and breathing in the smell of cigarette smoke and barbecue sauce, I was transported back in time to an all-too-similar scene when I was a child. Following nachos and guacamole galore, I managed to make my way down the street for a shopping expedition. The serious perks of Wicker Park lie in the low-price boutiques that resemble upscale shops. In other words, most stores I had the chance to explore gave me feelings similar to that of shopping a 50% off sale at Aritzia.

After a nearly perfect afternoon, I hailed a cab like a true Canadian dork and headed back to the hotel.

During the cab ride back, I couldn’t help but notice Chicago’s never-ending stream of art. I’m not just talking about the famous museums or attention-grabbing art fixtures scattered across the city. I’m talking about the exquisite details in each passing building; the diverse mixture of old and new.

As I watched the gradual transformation of rustic Wicker Park fade into the glass portrait of downtown, I felt overcome by feelings of nostalgia and futuristic wonder. From the magnificent six story Bloomingdales to the 100 year old Fourth Presbyterian Church down the road, Chicago not only offers a history lesson, but insight into the future—all at the same time.

If this isn’t what art is made to represent, then I don’t know what is.


Yours creatively,

Jaclyn Sanscartier, Online Contributor 

Photography: Jaclyn Sanscartier

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