That Trundlin’ Town – Things You Will See Driving in Chicago

Although driving your used Dodge Durango in Chicago is not quite the same experience as trying to get a Ferrari through LA traffic, it has a character all its own. For example, you will have to deal with more pedestrians and jaywalkers. You won’t be able to make sense of the highways unless you know the names of famous Chicago politicians. The downtown streets are often gridlocked.

None of this is unique to Chicago, but when patched together as a quilt, is makes for an experience unlike any other. Here are just a few things you will see.

Strange People

Middle-aged men driving convertibles in cold weather with the top down and the windows rolled up.

Farmers selling watermelons on the side of the road out of a truck in August.

Pickups dangerously loaded with junk car parts pulling onto the freeway.

Some creepy guy with a comb-over flirting with women in other cars. This activity actually has a name: “pulling a Sloane.”

Eric & Kathy billboards everywhere. I mean EVERYWHERE!

Jaywalkers studiously not watching out for traffic. Apparently, this is a ruse to fool the oncoming drivers who would otherwise take the maneuver as a deliberate affront.

Strange Activities

Roman candles and bottle rockets being lit in the middle of the street on or about Independence Day.

Traffic backed up for a block by someone trying (mostly unsuccessfully) to parallel park. This is related to a maneuver called “the Chicago kiss” in which the driver oscillates into a tight parking slot by making gentle taps with the bumpers of the other cars in front and back of him.

That long line of vehicles may look like it’s being held up by a cautious parker, but it’s actually the queue for a car wash, another phenomenon not unique to Chicago, but pretty close.

In Chicago, get used to being constantly passed by bicyclists going faster than your car.

You will be approached by strangers so often, mistaking you for their Uber lift, you might want to consider becoming an Uber driver.

Aging cars with visible salt erosion miraculously still functioning. (Did I mention something earlier about used Dodge Durangos?)

Toll booth mania. It’s an actual psychiatric condition, I swear. People will swerve across three lanes at the last instant to get in the shortest toll booth line only to find themselves behind someone who stopped too far from the change basket that he has to open his door to reach it. Another manifestation is when a driver discovers his I-PASS is invalid and tries to back out of the automatic lane to get into the cash lane.

Vaguely familiar flags flown from cars on foreign holidays.

Strange Sensations

The infernal (in the Dante sense) sulfurous odor you encounter with Indiana via the Skyway. No, it’s not a hundred Denny’s restaurants frying eggs.

Vehicles in front of you swerving suddenly to avoid bone-jarring potholes.

Teeth-rattling bass coming from a car you cannot see, but hear and feel.