Postcards from: Chicago, Illinois

Posted by Aileen Jang, July 16, 2015

"All of the lights"...Chicago by night. (Image courtesy of S. Chevalier)

A lover of music in all of its' glorious manifestations, I would be lying if I told you that my recent weekend trip to Chicago, Illinois wasn't, in some subconscious way, inspired by a couple of my favourite artists.

Sufjan Stevens devoted an entire album to the state of Illinois itself. Among the whopping 22-tracks in Come on Feel the Illinoise, Stevens includes a tune titled "Chicago", telling the tale of a young man on a roadtrip. With his hands on the wheel of his car and a youthful idealism in his heart, he reminisces about past mistakes on a road to self-discovery.

Yeezy himself even carves some time out his busy schedule of loving himself full-time, to pay some respect to the city in "The Good Life":

The good life, it feel like Atlanta
It feel like L.A., it feel like Miami
It feel like N.Y., summertime Chi
Ahhhhh! (Now throw yo' hands up in the sky)

With feelings of Chicago wanderlust charm stirred by Sufjan Stevens and the very brief but important mention of the city immortalized in a Kanye West song, I had my two pre-getaway pump up jams on repeat in my head to ready me for some Chi-town loving.


Possibly more cyclist-friendly than Toronto? (Image courtesy of S. Chevalier)

Expecting a weekend of rain, and of course, some harsh winds calling for sweater weather (Chicago is, after all, indubiously dubbed "The Windy City"), we had planned much of our sightseeing to happen from the inside looking out. But by some miracle, the weather held out and it was clear skies and sunshine through and through, allowing us to channel our inner flâneur and get our aimless wandering on. We explored one end of the city to another by foot, and when our feet finally gave out, we relied on our trusty Divvy passes, a super safe + efficient way to get around the city. "Safe?" you may ask in disbelief. Very much so, yes! With dedicated bike path lanes painted throughout the city streets and cyclist signals attached to every streetlight, Chicago is well on their way to becoming the best big city for bicycling in America.

Hey John Tory! I'm looking at you!


Pit Stop at Giordano's for a slice of that famous Deep Dish Pizza Pie (Image courtesy of S. Chevalier)


Cameras and cocktails atop the John Hancock Centre building (Image courtesy of A.Jang)


Obligatory tourist selfie at Skygate a.k.a. "The Bean (Image courtesy of S. Chevalier)


Feeling the Prohibition-Era vibes at The Green Mill Jazz Bar (Image courtesy of S. Chevalier)


Poppin' bottles - bubbly inspired art-deco architecture throughout the city (Image courtesy of S. Chevalier)

We made our way to districts like Logan Square and Damen, The Loop, Gold Coast, Magnificent Mile, Uptown, Oldtown + Lincoln Park, checking out the sights + sounds, and obviously, downing the delicious eats along the way. We were also sure to take advantage of the city's reputation as a craft beer capital. Thank God for all of that walking.

I don't think it's possible to fit everything in one weekend, and we never intended to attempt it; the city's got a lot to offer to tourists with a rich history visibly shown through architectural design, an awesome arts + culture scene, a booming foodie industry, great live music and nightlife. However, to experience Chi-town in all of it's full glory, would mean to experience it like a local, and to become a local would take years! This can really only mean one thing: a return trip in the very near future.

Although a quick Google history search on Chicago will tell you that the name roughly translates to "smelly onion", I think it's safe to say the city has many flavourful layers and has come a loooonngggg way from it's perceived unsavoury roots... heh heh!

A couple of tips + tricks from me to you:
1. If your accomodations state "close to subway line", it may mean at the cost of a good night's rest! Subway lines are predominantly above ground throughout the city. A blessing in many ways (cell service, awesome views) but a curse in others, but hey, beggars can't be choosers right?
2. A small, deep dish pizza at Giordano's is sufficient for two! Don't get overzealous and let your stomach do the deciding, even if you find yourself getting a seriously bad case of the hangries. Or you can just throw everything I just said out the window and go big or go home. Go ahead. Get the large. I double dog dare you. Not only will you be feeling that top-button-of-the-pants-popping kind of full, you'll have leftovers for days!

As a Torontonian, running through the 6ix with my woes can be great, but a short + sweet getaway to our neighbourly US and A can be veeerryyyyy niiiiice too (especially when Porter Airlines takes 50% off their base fare flights - why the heck not, right?). Planning a trip to Chicago in the near future? Here’s some starter places you should definitely check out:

Revolution Brewing
Lula Cafe
Girl and the Goat
Big Star Goose Island
New Wave Coffee
Intelligentsia Coffee
La Colombe Coffee
Stan's Donuts

Museum of Contemporary Art, Chicago
Art Institute of Chicago
Chicago Public Art

Shoreline Sightseeing Architecture Tours
Carbon and Carbide Building
John Hancock Centre
Millenium Park
Holy Name Cathedral
Marina City

Slippery Slope
Green Mill Jazz Bar
Navy Pier

*All images courtesy of S. Chevalier

Posted in: Hotel + Travel