Chicago
So as the clouds parted to make way for a grid of lights, I wondered what and who I would encounter over the next six weeks, and what neighbourhood, street, and bed I would call home. Thus began my first adventure in a city where I knew no one. My modern expedition if you will, of the town they call Chi.
Now, as I sit drinking oolong tea on an island off the coast of Panama, I put pen to paper to start my very first city guide. Let’s hope it goes well.
I’m not going to give you a fluffy-ass Lonely Planet guide, where I tell you about the typical shit that everyone does. I’m going to hit you with some knowledge that I wish I had known. So let’s get amongst it, and start off with a hugely important topic:
Pizza
So I’m starting with what Chicago is known for, but I don’t buy into this deep-dish bullshit. I’m talking about normal pizza. You need to hit up Pequod’s on Clybourn, it’s a classic spot. They do a caramelised crust for my deep-dish lovers – but the thin crust would stand toe-to-toe with any big dogs of NYC. Next, you’ll want to head over to Logan Square and holla at my homies from The Boiler Room. Situated right under the California stop on the Blue Line, it’s a must. For $8.50, you’ll get a slice, a tall PBR can, and a chilled shot of Jameson – they call it a PB&J. I asked my man Alex why they put cornmeal on the base and he said, “Because it’s awesome!” That’s a good enough reason for me.
Burritos
Now let’s keep this food coma going with some Mexican love. Hit up Picante on Division in Wicker Park for some killer, super fast "white boy" burritos (a term I use to describe the super simple tomato, lettuce, cheese, beans, and rice combo). Also, in Logan Square, you’ve got El Charro and Puebla, which are both mean.
Homie Tip – get your burrito turned into a suiza at Puebla for an even cheesier feed.
All three are open super late as well. I’ve surprisingly had burritos all over the city, but the north-west side just had it down. But, if you are on the south side or are in the mood for more of a restaurant vibe, hit up La Cantina on Michigan – straight dope!
Graffiti
Now one thing that the south side does have over the north is graff. Hit up Little Village area - on Kedzie - between 24th and 30th. You could also head over to Pilsen - to kick it with the Polish homies – I’m looking at you, Jess! Just jump on the Pink Line and get off at the 18th Street stop, and you’ll find tonnes of stuff.
Fun Fact – I was stranded in Pilsen at around 1 a.m. and tried to walk to Wicker Park. After I’d walked ten blocks in the wrong direction, I found a taxi whose driver asked, “What the hell are you doing here at this time?” I ended up sleeping on a hardwood floor with no pillow or blanket that night.
Coffee
There’s also some paintings up in Logan Square, near the train line, and while you’re over there, head to Fullerton and Milwaukee to grab a coffee at Gaslight. Super chill spot, with friendly staff – probably too friendly when it comes to Aussie standards.
Fun Fact – One time, as I handed back my coffee cup and said “Thanks,” the barista replied, “No, thank you!” to which I thought, “Fuck you, buddy – you ruined it!”
The other caffeine spot that I frequented was La Colombe in Wicker. These guys had it down, always on point, remembered my order, and were great to have a chat with.
Homie Tip – head around the corner to Myopic Books on Milwaukee to pick up a secondhand read for when you’re drinking your coffee.
Fun Fact – the day after I bought a book on Sugar Ray Robinson, my bag was stolen out of my mate Demon’s car – never even read a page.
Veg Food
Now for my favourite vego spots. For sandwiches (and I don’t mean normal sandwiches, I mean out-of-this-FUCKING-world sandwiches) – hit up Ground Control on Armitage and have a Jibarito – shit son! Think of a burrito, but in-between two big patacones that act as bread.
For a variety of veg food, check out Chicago Diner – there’s one in Logan Square and one in Boystown. For a small bar vibe or maybe even a possible date spot, go to Handlebar on North. They also cater to pescatarians. Some great food was eaten there on my first night out in Chi. Asian vego fans must head over to Dragon Lady Lounge in Avondale – which is just north of Logan.
Now, onto a couple of spots that although aren’t all veg, but are at least veg-friendly. Five Star Bar in Noble Square has a pretty good veggie burger if you want a rock’n’roll pub setting while you watch a Blackhawks game. Going back to my Asian fusion homies, check out Rodan in Wicker.
Fun Fact – I went to Rodan on a blind-double-date with Demon and two girls, one French, one German. After chilling a while, listening to some sweet rap music and mingling with the local hip-hop/graff crew, the German must have been over the awkward conversation. Either that, or she was more annoyed by Demon trying to compliment her (by saying that she had a "fat ass") than she let on, and finally asked, “Could we go somewhere that plays ‘real hip-hop’, like Drake or Lil’ Wayne?”. Realising that she was clearly a moron, we all went back to Demon’s place, where his big move was saying, “Come on, girl, you know I like that big ol’ booty.” About ten minutes later, we dropped them at the train station and went out for burritos.
Skateboarding
The skate-ability of Chi is less than I thought it would be. Of course there are parks, but most of the footpaths and roads I encountered were super fucked up from the winter, but do check out Uprise Skateboards, a well-roundedskate shop – the boys there are top lads as well.
Public Transport
The transit system is super easy. Buses run on the grid, and trains are colour-coded. Just pick up a Ventra card for $5 and load it with some money to use as credit for your fares. The train system is known as the "L", since it's elevated for a huge portion of it. A lot of the names of stops are simply the street names, so make sure you're on the right line (simply which colour it is), as there is more than one Western stop, etc.
Homie Tip – register your card online to get the $5 you spent on it credited to your account. You can also pay bills and what-not with your card.
Weather
The weather is lovely in the middle half of the year (and that’s pushing it), but I wouldn’t recommend going at other times as it can drop to as low as -40 degrees.
Sights
I didn’t do too much touristy sight-seeing (which, as Alan Watts also says, is a stupid phrase), but The Art Institute of Chicago is great, and free on Thursdays from 5 p.m. - 8 p.m., but you’ll need more than just one night to see it all. Lincoln Park Zoo is also free, and you might as well go and take a typical reflection shot from The Bean in Millennium Park. Also, you could just stroll around the Lakefront Trail (which is an 18 mile stretch), or maybe even Hyde Park (which is on the south side). Demon also painted a piece in an alley next to a pizza shop down there. Why not check out the Chicago Water Tower, which is one of the oldest structures in Chicago (since it’s one of the few that survived the Great Chicago Fire in 1871)? Also, you might as well see a Bulls game at United Centre.
Chicago is one of my favourite cities in the world, and my top pick when it comes to North America. Check it out, and tell me some joints that I should check out next time I’m there. I know that my guide is fairly north-west-side-based, but I promise to explore other spots next time.
I lastly want to thank you everyone who made my time in Chicago a great one. The guys from The Boiler Room, especially Alex and Bobbi. My homies at Chicago’s Best Barbershop, for helping me out with some trims. Jason, Disco, Ceno and Demon, who were my first friends there, and most importantly, Nanette and Andre, who put me up for what was originally supposed to be 1-3 weeks.
I’ll miss you, 111th Street.
