CITY SPOTLIGHT: Chicago, IL

on November 1, 2018
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Discover Some Hidden Gems in the Windy City

Sajae Elder, WKND Contributor

If you’re looking for great food, amazing architecture and incredible hidden gems, Chicago makes for the perfect weekend getaway, jam-packed with things to see and do – especially ones a bit off the beaten path. The Windy City is only an hour and 40 minutes away from Toronto, and a flight from Toronto costs around the same as one to New York City – sometimes less – which makes it perfect for budget-friendly trips.

Chicago is one of the most dynamic cities in the United States and its second most-visited. With no shortage of draws that pull in millions of tourists year after year, the real fun lies in the city’s less touristy haunts. In a city with a rich history, it’s easy to make a scavenger hunt out of your weekend – finding some of the city’s best hidden treasures.

FIND THE BEST HOTDOG

image of a hot dog from Alexander JimsFoodies can indulge in city favourites like Chicago’s famous deep dish pizza at Pequod’s Pizza or chow down on an authentic Chicago-style dogs topped with chopped onions, dill pickle, tomato and all kinds of fixings at Jimmy’s Red Hots (#NoKetchup) or Fat Johnnie’s in the city’s Southside.

Sculptures and public art are a big deal in Chicago, and while the most obvious place to be is Cloud Gate, or “the bean” in Millennium Park, there are other gems like the – ahem – Shit FOuntain sculpture in the city’s Ukranian Village, or the worldly bricks of the Tribune Tower. Here, you’ll find pieces of the Great Wall of China, the World Trade Center, Great Pyramid of Giza, and the Taj Mahal.

SEARCH FOR SECRET SPOTS

As the birthplace of House music and home to thriving Jazz, Indie Rock, and Hip Hop scenes, there’s no shortage of legendary nightclubs and live music venues such as The Drop Lounge, Buddy Guy’s Legends, or Hydrate. On any given night, you can find underground locales that look very much like the speakeasies they were when they first opened during the Prohibition Era like Coco Club in Brighton Park; with live entertainment to go right along with the great cocktails, and the secluded Pickwick Lane alleyway location of Asado Coffee.

Much like the prohibition days, there are still some locations in the city that are much more than meets the eye. While the legendary Mr. Flower and Mr. Ping Pong – a flower shop with ping pong tables at the back – is now closed as of this summer, the idea seems to have spread throughout the city. You can try to get into the 24-hour, members-only Chi-Slam Table Tennis Club which is in…a secret location! You’ve got to call to get the new address from a mysterious guy named Ardy.

FOLLOW IN FAMOUS FOOTSTEPS

History buffs will get more than a kick out of the rich history that courses through the streets. The city that made Al Capone still has plenty of spots he reportedly frequented, including Chicago Pizza and Oven Grinder Co. and the stunning architectural gem, Renaissance Blackstone hotel, where Capone himself stayed many a night. If comics are more your speed and you have a few hours to take a day trip just outside of the city, consider heading to the Super Museum in Metropolis (yes, the real one) to see the largest collection of Superman collectibles.

If there’s one thing to be said about Chicago, it’s the beautiful buildings that can be found all over the city. From pubs to beautiful commercial skyscrapers to government buildings that have been there since the 19th century, you’ll find the perfect balance of old and new. For those ready to dive deep, you can bounce around the city to see the work of famed architect Frank Lloyd Wright, whose career got its start in Chicago, by visiting places like Robie House located close to the University of Chicago campus, and the light court in historic Rookery Building.

DISCOVER ART IN THE STREETS

Sculptures and public art are a big deal in Chicago, and while the most obvious place to be is Cloud Gate, or “the bean” in Millennium Park, there are other gems like the – ahem – Shit Fountain sculpture in the city’s Ukranian Village, or the worldly bricks of the Tribune Tower. Here, you’ll find pieces of the Great Wall of China, the World Trade Center, Great Pyramid of Giza, and the Taj Mahal.

For the ultimate adventurer, there just might be a scavenger hunt built right into the city. Scattered all around the city, you’re likely to come across directional star symbols that lead to the next one and so forth, for miles on end. How or why they even got there is still a mystery, as well as what comes at its end, so why not try to find out this weekend?