Truck Driving Stories About Chicago, IL

Truck driving jobs in Chicago, IL can be brutal, unless you absolutely love heavy traffic and terrible winter weather. A career as a truck driver wouldn't be complete without a lot of time sitting in traffic in the Windy City. Actually, I never felt getting around Chicago was all that bad. I grew up in Buffalo,NY and that city is more difficult to get around than Chicago. If I had to take a local trucking job, I would choose Chicago over Buffalo. Although I will admit there is a lot of people that would disagree with me in a big way.

Anyhow, Chicago is one of the largest trucking hubs in America. I have probably spent more time there than in any other city in the country. Fortunately, I kind of liked driving there. I felt comfortable for some reason. I haven't a clue why. It just seemed like a cool place to be.

So anyhow, one night I had to go right to the center of downtown to pick up a trailer off of one of the railroad yards. It was a Friday evening, around 6:00 or so. The traffic wasn't too horrible, surprisingly, because I came in on the tollway. That's the only way to go, believe me. So I get into downtown, sit in a bit of traffic, get off the interstate, and figured I had it made. I pick up the trailer, start cruisin out of the city, and get my delivery made the next day in Columbus, OH. And as always, right when you think you have it made, that's when it all went wrong.

truck driving stories chicago

There were two overpasses, one on either side of the entrance to the railyard. They were only about 300 feet apart. I went under the first one and began to make the left into the railyard. There was an incline going into the yard and the truck tried to downshift into 2nd gear - the truck was an automatic. Just then the engine revved and the truck came to a stop. I hit the gas - but nothing. I was halfway into the yard, blocking not only the entire roadway, but also the entrance into the yard. Traffic came to a stop in all directions.

OH MY GOD!

I had been driving for many years at that point so there was no panic, nor was there any surprise. Sh*t happens when you least expect it. Well, my company called a tow truck but that was gonna take a half an hour or so. Turns out there were two city buses full of people that were blocked in, along with about 150 cars and trucks.

Unbelievable.

driving a big rig down the highway

So the Chicago Public Transportation Supervisor had to come down to see what was going on because of the buses. The railway supervisor had to come down because I was blocking the entrance to the railyard. The police had to come down because of all of the traffic being blocked. So after talking with all of the authorities on the matter, I did what any other driver would have done when blocking many hundreds of people from getting where they were going - I locked the doors to the truck and walked around, blending into the crowd like I was just another bystander wondering what was going on!

"What happened?" one person asked. "I guess something went out in the driveline I heard" was my reply - clearly implying I had no real way of knowing - and certainly not disclosing that is was my truck! Whose truck? My truck? No my truck!

Well, it all ended well anyhow. They towed the truck out of the way, and the tow truck driver figured out that an air line had let loose to the transmission and he was able to fix it on the spot. Lucky me.

The moral of the story? For one - don't hit anything. No matter what happens, dont run into anything. Eventually any situation will go away like it never happened. And secondly - lie. Don't ever tell anyone other than the authorities that you are the one clogging up downtown at rush hour and everything will be fine! :-)

Until next time - here's more resources for ya:

red peterbuilt ask a truck driving question

For questions about becoming a truck driver, we highly recommend:

Find truck driving jobs and schools
TruckingTruth and BigRigDriving are owned by Brett Aquila, a 15 year truck driving veteran with 1.5 million miles covering all 48 continental states and a large portion of Canada

BigRigDriving is for those interested in research, debates, and discussion of topics within the trucking industry

TruckingTruth is dedicated to those considering becoming a truck driver or are new to the trucking industry

Becoming a truck driver book, truck driving book

Becoming A Truck Driver: The Raw Truth About Truck Driving

- By Brett Aquila

If you're considering becoming a truck driver, this is the book for you!

Becoming A Truck Driver

Our Guide To Becoming A Truck Driver will help get you started in the trucking industry

Choosing A CDL School

We have a series of articles that will help you understand how to choose the right truck driving school

Company-Sponsored School

We have a ton of information on the company-sponsored CDL training programs.

Truck Driving Schools

Here you'll find our directory of truck driving schools by state.

Truck Driving Jobs

We have a fantastic listing of truck driving jobs. Fill out all the apps you like!.

Truckers Forum

We have the friendliest and most helpful trucker's forum you'll find anywhere.

CDL Practice Tests

Test your knowledge and prepare for the CDL exams with free online CDL practice tests.

Truck Driving Blogs

Over 300 articles from more than 30 authors in our truck driving blogs..

Pre-Trip Study Guide

Get ready for the pre-trip inspection CDL exam with our free online pre-trip inspection study guide.

Our Most Recent Trucking Blogs

Reaching 300,000 Miles In A Big Rig

Posted on 26 January 2012

I had never planned on driving a big rig so you can imagine how exciting it was for me to reach the 300,000 mile barrier! Continue reading

Factors Affecting Job Placement In The Trucking Industry

Posted on 29 December 2011

There are a lot of factors that will affect your ability to find job placement in the trucking industry. Not only the obvious ones like employment history, criminal history, and driving record, but also things like your physical health and credit scores. Let's take a look at em.... Continue reading

4 Mistakes That Cause Students To Fail CDL Training & How They Can Be Prevented

Posted on 28 December 2011

While the majority of students have success during their time at CDL training, there are others who come up short in their quest to become a professional truck driver. So, why do they fail? And how can it be prevented? Let's take a look at the four most common mistakes and how to prevent them. Continue reading

Understanding Pre-Hire Letters: The What, Why, And How Of This Important Step

Posted on 21 December 2011

Getting pre-hires is an important step when beginning your truck driving career. They can verify that companies are willing to hire you, and give you numerous choices when it comes to choosing the company you'd like to work for. Here we'll go into detail about what a pre-hire is, and how to go about getting them. Continue reading

The Sleep Apnea Witch Hunt

Posted on 15 December 2011

Sleep apnea is the biggest buzz in the trucking industry right now. But is this justified? Or is it yet another money-making scheme for the insurance companies and medical industry? The statistics are fuzzy. Continue reading

5 Advantages of Company Sponsored CDL Programs vs. Private Truck Driving Schools

Posted on 13 December 2011

There are a number of advantages to company-sponsored CDL training over private truck driving schools. Here we'll talk a little bit about the differences between the two, and why you may find that company-sponsored training is the better way to go. Continue reading

The Next Chapter In My Trucking Journey

Posted on 14 November 2011

I've seen more of this country in just a few short years than most people see in their entire lifetimes. But most things eventually come to an end. In this case, my trucking career has ended as I move on to other things. I'd like to summarize why I left the industry, and where I'm headed now. Continue reading

A Driver Trainer’s Perspective: Some Helpful Tips And Observations For Student Drivers

Posted on 14 November 2011

Being a CDL instructor or a driver trainer is a very unique experience. I learned more about truck driving over the past 4 weeks than I have in the previous three years combined. It was an amazing learning experience for me. Here are some of the highlights I learned along the way. Continue reading

CDL Testing Day From A Trainers Perspective

Posted on 9 November 2011

After four weeks on the road training my student, it was time to sit back nervously and watch as he attempted to take the CDL exam to get his license. My student and I were extremely nervous, and it didn't go quite as well as we had hoped. Continue reading

OTR Training- Week 1: Patience and Perseverance

Posted on 25 October 2011

Becoming a solo truck driver is one of the hardest things I have ever done in my life, and I have done some hard things. CDL training will test you in so many ways, and it will go far beyond your ability to drive a truck. Continue reading

(click to show more blogs)