The Chicago Roll is a driving technique used to merge into or pass through heavy cross traffic at an intersection. While this style of vehicular suicide may not be endemic to the city of Chicago, it was the first place I never noticed it done on a regular basis.
Let's say that you're at an intersection, and you want to turn left. The road that you are currently on is a side road that has such low-traffic that it necessitates only a stop sign, and not a traffic light. The cross street is a four-lane, high traffic artery. The traffic on this street is so heavy that the traffic never actually relents to the point where you can get across safely. So, you'll be sitting here until the end of time as traffic rushes by.
Fear not! The Chicago Roll will help you avoid the need to be patient. It's also a great way to completely disregard the rules of the road!
The basic Chicago Roll is achieved by simply taking your foot off the brake, and gently applying the gas pedal. Your car will begin rolling into oncoming traffic. This forces the oncoming traffic to come to a screeching stop, lay on their horn, and let you cross their lane. Just continue rolling across all the lanes of traffic, sending oncoming traffic into a snarl of near miss accidents and blue language, until you have crossed the artery.
Congratulations, you have defied death and completed a Chicago Roll! You are also, coincidentally, a gigantic asshole.
Once you have mastered the basic Chicago Roll, now you can start to add finesse to your law-breaking ways. There's such a wide variety in styles, that you are bound to find one that suits you.
The Studder-Step (aka The Psychotic Bastard, The Juke): Instead of simply rolling out into the middle of the street, hit the brake every once in a while, like you are reconsidering your stupid decision to play in traffic. This will keep the oncoming traffic on their toes, as they are not truly sure if you're going to spontaneously throw your vehicle into reverse. There is also a Modified Studder-Step, where the break pedal and gas pedal are alternated to create a rhythmic dance of doom.
The Lunger (aka The Brazen Prick, The Cannonball, The Speedy Death): If you're going to perform a moving violation by doing a Chicago Roll, why not ignore that stop sign as well? As you approach the stop sign, don't bother looking to see if there is any oncoming traffic, and just floor it instead. Oncoming traffic will be paralyzed with fear as your car comes hurtling out of the side street with breakneck speed! This technique also works when coming out of alleys, parking lots, and sidewalks!
The Piggy-Back (aka It's Amateur Night!, Group Solidarity): Say there is someone in front of you at the stop sign. You're pretty sure that they're going to do a roll. What can you do to expedite your progress across the street? Pull up right beside them (preferably on the side away from oncoming traffic), and both of you can cross to the median at the same time. For crossing further lanes, the vehicle next you now becomes the passenger, and you are the one giving the piggy-back. After all, if you're going to break the law, you might as well get as many accomplices as you possibly can.
The Domino Effect (aka The Psych-Out, The Pinch, The Funnel): Instead of gently rolling into oncoming traffic, try to edge your car out just enough that you're slightly in the oncoming lane, and then stop. Oncoming traffic, expecting you to gently stroll into their lane will be stupefied as you maintain your position. This will make them antsy enough that they will begin swerving ever so slightly into the next lane to avoid you, which causes the traffic in that lane to ever so slightly veer into the neighboring lane, which contains head-on traffic. Two things will happen: traffic will become condensed, so that you're only really crossing two lanes of traffic (much easier), or a vicious accident will occur in the middle of the street, bringing traffic to a stop and therefore allowing you to pass safely.
Waiting For the Bus (aka The Human Shield, Your Tax Dollars At Work): This one is an advanced technique, recommended only for the truly suicidal. If the corner to the left has a bus stop, wait for a bus to arrive. Immediately pull out in front of the bus. The bus will then attempt to merge into the neighboring lane, causing the traffic there to stop. Immediately pull out in front of the bus again, causing the bus to block both oncoming lanes, and granting you safe passage to the median, where you can proceed with your roll. The only downside occurs if the bus doesn't actually stop at the bus stop, in which case you will get a great opportunity to investigate your innards as they a crushed into a damp puddle under the bus. But, hey, you'll get on the local news!
Why The Chicago Roll Works
The reason that the Chicago Roll works so successfully is two-fold. First, oncoming traffic will try very, very hard not to hit you. They are not critically insane accident lovers like you are. Theirs is a world of flowers and bunnies and balloons. The last thing they would want to do is cause any damage to personal property, or even kill someone by not taking every precaution available. I have not seen, but would not be surprised to hear about a car driving up onto the sidewalk and through a store window in order to avoid another car performing a roll.
Secondly, traffic laws in most areas (including Chicago) almost always give fault in a car accident to the vehicle that caused the impact. In this case, if an oncoming vehicle t-bones your car, they are at fault. Their insurance will cover the damage to the car, and you can sue sue sue to your heart's content. Oh, happy day!