The Benefits of Truck Driving Jobs in Chicago


Being a truck driver comes with several enticing advantages. A truck driver, for example, gets to travel as part of their profession, while others have to schedule out time to travel. If you’re considering or continuing a career as a truck driver, you should be aware of the advantages that, specifically, come with working in the state of Illinois and even better, Chicago. In this post, we’ll cover the top three benefits of truck driving jobs in Chicago.

Great Pay

We started with the most important and appealing reason. Truck drivers in Illinois get top pay! According to, if you live or work in “the prairie state”, you already live in a higher-paid state for truck driving jobs as you can see on the map below. More specifically in 2021, truck driving jobs in Chicago paid an average salary of $56,840. At K&B Transportation, we are proud to pay our drivers a salary way above average! K&B road warrior drivers in Chicago can earn up to $90,000+ annually. Next, we’ll explain your job options and the awesome pay for each.

Truck Driver Job Options in Chicago

With Illinois being in a prime location in the U.S. and with Chicago being a major import and export hub, you have some options. K&B Transportation has four different job options for you; a dedicated driver, a dedicated driver with home weekends, a traditional OTR driver, and a road warrior driver. Here are the differences:

  1. Dedicated Drivers – Starting pay up to $1,575 Weekly – Stop worrying about miles with a salaried position that gives you top pay regardless of miles. Also, enjoy the steady workload that a dedicated shipper offers!  
  2. Dedicated Drivers with Home Weekends Starting pay at $1,125-$1,237 Weekly. If you want to forgo your home weekends, you’ll get an increase in pay for running over the weekend!      
  3. Traditional OTR Driver – Starting pay at .60 CPM with .01 CPM raises at 6 months, 1 year, 2 years, and 4 years. Drivers are guaranteed $1,500 per week minimum, but can earn up to $1,800 on top weeks!
  4. Road Warrior Driver –  Earn up to .70 CPM with a $1,625 minimum guarantee! Drivers who choose this option must be willing to stay out 2 months at a time and then go home for ten days. 

All of our drivers also enjoy; 2020 and Newer Freightliner Cascadias with APUs, Refrigerators, and 100% Automatic;
excellent health, life, and dental insurance; safety, clean inspection, and referral bonuses, as well as a flight to your orientation. 

If you’re still not convinced about truck driving jobs in Chicago, let’s talk about what the windy city has to offer when you’re off the clock.

Things to See in Chicago

As with most of our great 50 states, Chicago has plenty to offer for food, sightseeing, and entertainment. Although there is a long list of fun destinations in Chicago, we choose the top three options that we liked the best. 

  1. Chicago Pizza Tours – Original Chicago Pizza Tour
    Pizza tours in Chicago are a fun way to learn about the city’s most famous culinary export. In 2020, the excursions were upgraded to incorporate a bit more luxury. There are four different tour options; The Original Chicago Pizza Tour, Chicago Pizza & Cocktail Tour, The Big Shoulders Downtown Tour as well as Private Tours. The Original Chicago Pizza Tour is the most popular. It includes stops at four pizzerias to sample more than six pizza slices. You’ll learn about the history, ingredients, and physics of making the best pizzas. And, you get to explore the taste and history of four different Chicago neighborhoods.

  2. CUBs Baseball Game at Wrigley Field
    Get the full Chicago experience at Wrigley Field. With a hot dog, a beer (for those over 21), and some peanuts, you can’t go wrong watching one of the founding teams of the National League. The Cubs, first known as the White Stockings, became the Chicago Cubs in 1903. As long as you can find a game that fits your truck driving schedule, this is definitely an entertaining way to spend an afternoon or evening.

  3. Chicago Gangsters and Ghosts Walking Tour
    One of the best ways to get to know the infamous city of Chicago is to enjoy a guided Chicago Gangster Tour or Ghost Tour, which details the crimes, transactions, and charm that helped shape the city into what it is today. They provide a two-for-one deal by providing historically-based guided tours of Chicago’s gangsters as well as ghost stories, all from the heart of the Chicago Loop Vice District. You’ll have a rare chance to tour these infamous haunting locales and historic crime scenes where it all happened 100 years ago.

Now that we’ve told you about the great pay, job options, and things to do in Chicago, we know you want to be on the K&B team! If you have a Class A CDL and 1 year of OTR experience, you’re the perfect fit. Start your application below and we’ll give you a call! 

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The History of K&B Transportation

With more than 35 years of expertise, the owners and executives at K&B Transportation know how to support their drivers, keep their fleet operating smoothly, and foster a culture of hard work so their drivers can succeed.