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How to Bicycle Like a Real Chicagoan: A FAQ

How to Bicycle Like a Real Chicagoan: A FAQ

It’s a given that Chicago is a very ideal bicycling destination. The flat terrain makes it easier to cycle there than it does in a lot of other cities, lots of nice bicycles lanes make it convenient, and the constant traffic congestion means it will be easier to get where you’re going on a bicycle than in a car. But what, you ask, is the story with bicycling in Chicago? What should you look out for and expect? How can you make the most of a real Chicago bicycling experience? I’m glad you asked, because here I am to give you the best advice you’ll ever hear about cycling in Chicago!

I don’t actually want to bicycle in Chicago. It’s windy, cold, and the sky always looks like a harbinger of doom.

Wuss.

But I didn’t bring my bicycle with me!

That’s not an excuse. There are many bicycle share and bicycle rental programs floating around in Chicago, many of which will lend you a perfectly good bike for half a day or a day for a reasonable price. Dish out the cash, then you’re free to use your bicycle any way you want! Ride in Critical Mass with your rental!

How do I deal with the cold?

Dress for it! Gloves and something to cover your ears with are both a big help. Wear nylon pants to keep the wind and any rain or snow off. Don’t skimp on the socks.

Oh no, my bicycle was stolen! How?

You locked it up with a cable lock, didn’t you? Yeah, they’ll cut through those things like hot butter. You need a good padlock, save the cables for making sure the seats don’t get stolen.

Why did you just smash that car’s rearview?

What, did you miss the part where he cut me off, braked right in front of me, then sent a whole red light screaming at me and honking his horn despite the fact that he couldn’t actually go anywhere at the time? Or the fact that he went around the block to tailgate me, or that he drove the wrong way up a one-way street? Well, rearview-smashing is our way of getting even. Motorists don’t care if they kill anyone, but hit them in the wallet, and they’ll think harder next time. Maybe. Hopefully. They’re motorists, so you can never be sure.

Where is the best place to begin a good bike ride in Chicago?

You’ll want to get on the Lake Shore Trail somewhere around the Shedd Aquarium or Soldier Field. Head north from there. When you get up to about Grand Avenue, head west until you get to Milwaukee Avenue, then ride up Milwaukee. That’s a nice way to begin. Or if you’re setting out on the last Friday of the month, go to Daley Plaza at 5 PM and ride in Critical Mass.

What about my plans to see the Magnificent Mile and Willis Tow-ow! OW! Why did you just stab me?!

So, are you really visiting Chicago just to see the national retail chains? Tourists visit the Mag Mile, and the drivers there all want you dead. You’re insane to try cycling up the Mag Mile. The cars swerve in every last direction without warning. And the Sears Tower is the tallest building in the city, and you can see it easily enough from the Lake Shore Trail. And I stabbed you because it’s called the Sears Tower, not Willis Tower, no matter what the popular news and travel outlets and insurances companies try to cram down your throat! You want to throw away money, do it in the small, local, and, you know, unique boutiques and quirky places along the Milwaukee strip in Bucktown. Or for god’s sake, at least Clark Street if your tastes are really that mainstream.

Is there a good place to get a Chicago-style hot dog on the way? And… Crap, I can never remember all the proper ingredients!

Dogs in this city are a dime a dozen. Surely you can find them easily enough along Milwaukee, or back down Clark, where I’m also going to send you. And don’t worry about remembering what’s on top of one. The guys making the dog will remember, which makes them a step up from any of the people who don’t work for hot dog joints. No one remembers all the toppings on a Chicago dog. If you’re getting a dog and can’t remember what the topping are, just use ketchup. I don’t care what those ridiculous cultists who are all opposed to ketchup on hot dogs say. Frankly, I can’t stand mustard, and among those cultists you’ll be hard-pressed to find anyone who actually has celery salt in their pantry. Don’t worry about the Chicago dogs. Worry about a proper Chicago-style deep dish pizza.

So, back to Milwaukee, where do I go after going up that street?

You’re free to hang east at Belmont, but if you want to see some of the most interesting neighborhoods in the city, wait until Lawrence. No matter which one you choose, you’re heading back to Clark.

Oh god, there are hipsters in Bucktown!

Yep. They may be annoying, but look at the bright side: They’re not trying to kill you.

What’s so special about this route, anyway?

Good, wide bicycle zones, considerate drivers, and good asphalt. Be picky about your favorite streets because some look like they’ve been through a war. Parts of Lake Street were capable of ripping the treads off a Sherman when I was living here. On the subject, LaSalle is also highly reccomended. Franklin used to be really awesome until they made it two-way. Now it’s merely awesome. Damen is a wonderful ride as well. On the South Side, be sure to visit Bridgeport and Bronzeville.

What about Hyde Park? That’s President Obama’s neighborhood!

Yes, I’ve had that Obama factoid drilled into my head. No, I don’t know where his house is. Anyway, what are you, rich? Go to some real neighborhoods. Live a little.

Hey, it’s Wrigley Field!

You don’t need to be at Wrigley Field to experience the ambience of a Cubs game. Go see a White Sox game. Watch actual baseball.

Wow, this is a big city! I’m starting to hurt!

It happens.

Why are you stopping at this bar?

I need a drink.

What, now?

Hey, you said you wanted to bike like a Chicagoan. Drinking before, after, and during a good bicycle ride is a proud Chicago tradition! If you’re in Critical Mass, it’s practically required!

What’s this Critical Mass thing you keep talking about?

A giant bicycle ride on the last Friday of every month where cyclists dress up in their peacock best and join together for a long bicycle ride! In good months, there are usually several hundred participants. Great way to see cycling as a subculture!

Who are those nutcases with the bags who keep zooming around The Loop?

Bike Messengers. Don’t mind them. They have work to do. Good folks. I did that myself for awhile.

Christ, didn’t you ever get hurt?

Thousands of times! Several doors, several cars, angry pedestrians, and the times when I was just carrying something big and lost my balance. That movie Premium Rush is more accurate than you would ever believe.

How long did it take to recover from all those accidents?

In the most severe cases, a day. That’s how long it took me to get back to work. I couldn’t go to the hospital most of the time.

What are you, crazy?

That’s what everyone keeps telling me.

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About Nicholas Croston

I like to think. A lot. I like to question, challenge, and totally shock and unnerve people. I am a contrarian - whatever you stand for, I'm against.

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