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12 Hours In Chicago

The first time I went to the Windy City, I was with my friend Cece on an overnight layover. We were jet lagged, so it was easy to stay up late and explore.

There wasn't a lot of time but we still wanted to experience all we could eat, drink and see.

Here's how we spent a little over 12 hours in Chicago:

EAT

I DON'T EVEN CARE HOW BASIC THIS MAKES ME, I had to have deep dish pizza.

I'd been warned that deep dish pizza, REAL CHICAGO deep dish pizza was unlike anything I'd eaten before.

This was not a lie.

Real, true, deep dish is honestly more like a lasagna than a pizza if you ask me. The layers of crust, sauce, cheese and toppings seem never ending. I'm not even really sure how we had energy to continue the night after this, but somehow we did.

It was a toss up between going to Pequod's and Giordino's, who won out. Our hosts had a difficult time picking one to recommend, but Giordino's was it. I couldn't tell you which pizza is better; but I can tell you this was damn delicious and I still occasionally find myself waking up from my sleep, drooling, and dreaming of it.

DRINK

When time is of the essence, one must make every moment, or in my case, every drink count.

The word was that Wicker Park was the neighbourhood to be in, with cool bars and pubs.

We got initiated into the Chi-town bar scene by a friend and Chicago local. We planned to go to Emporium, an arcade style bar but learned that it kinda sucked and most of the games were broken anyway. My Chicago pal insisted on meeting us at a real dive bar (not a hipster dive bar, a TRUE dive bar) called Inner Town Pub nestled between Wicker Park and Ukrainian Village.

He quickly bought us a round of shots that could have put more than hair on our chest. Malort is a cult famous Chicago liqueur that is a lot like what I'd imagine pesticide to taste like. AWFUL. It's bitter and now that I've had it, I hope to never taste it again. But my friend assured us we could truly hold our own in the Windy City now.

SIGHTSEE

Cece taught me the ultimate Chicago tourist travel hack; YES go up to the John Hancock Tower, but NO going to the observation deck.

Save your $20 for an overpriced drink one floor up at the bar.

The Signature Room sits on the 96th floor and offers panoramic views of the skyline for no charge, except for patronage.  As an added bonus for women identifying folks, the bathroom offers a breathtaking look over Chicago while you do your "business".

Following our beverage at The Signature Room, we moseyed back down to ground level to check out the famous Bean sculpture (really called "Cloud Gate" by Sir Anish Kapoor) although it was pretty tricky to see at night time.

We called it quits to our sight seeing to make way for some nightlife (and Malort) and continued our brief tourist mission the following morning. We borrowed bicycles from our amazing Airbnb hosts and decided to hit the city that way.

We rode down to the water and had a gorgeous view of Chicago from the south side. We also rode to one of the most important places I could ever think of; 2120 South Michigan Avenue; home to legendary Chess Records. This was the most famous location of the studio, where heaps of classic records were recorded between 1956 to 1965. Artists like The Rolling Stones, Willie Dixon, Howlin' Wolf & Chuck Berry recorded here, among so many more.

I was heartbroken that on the day we went, the street was having a power outage and the studio was closed. Normally it is open to do tours, but just getting to be there and stand in the door way was still pretty cool.

Following our bike ride, we returned to the airport and made our way home to Toronto. 12 hours isn't really enough time in a city this big, but it was still enough time to eat, drink and see the skyline.

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