Thinking about taking control of your trucking career and hitting the road on your own terms? You’re not alone. Owner operator jobs in Chicago are booming, and for good reason. With its central location, massive freight traffic, and endless routes in and out of the city, Chicago has become a hotspot for truck drivers who want more freedom—and bigger paychecks.
Whether you’re already behind the wheel or just exploring your options, this guide will walk you through everything you need to know about becoming an owner operator in the Windy City. We’ll break down earning potential, local vs long-haul opportunities, the best companies to work with, and what it really takes to run your own rig.
If you’re ready to move beyond the standard company route and build something of your own, this post is for you.
Why Chicago Is a Prime Spot for Truck Driving Jobs
If you’re looking for steady freight, competitive pay, and access to some of the busiest shipping lanes in the country, Chicago should be at the top of your list. It’s not just the deep-dish pizza and skyline that make this city famous — it’s also one of the most important logistics hubs in North America.
Located at the crossroads of several major interstates (I-55, I-90, I-94, and more), Chicago connects the East and West Coasts, the Great Lakes, and the entire Midwest. That means goods are constantly moving in and out of the area, and the demand for truck driving jobs remains consistently high — especially for skilled drivers who are ready to take on more responsibility.
But it’s not just about long hauls. There’s been a noticeable rise in local owner operator jobs around the city as well. Suburbs like Joliet, Cicero, and Elk Grove Village are home to large distribution centers, rail yards, and warehouses that need dependable drivers for local and regional routes. These types of positions are ideal for drivers who want to stay closer to home while still earning a solid income.
Whether you’re aiming for cross-country routes or short-haul deliveries within Illinois, Chicago offers a mix of opportunities that few cities can match. And for those ready to transition into owner operator jobs, that constant freight flow means there’s no shortage of loads to keep your wheels turning.
In short? If you’re a truck driver looking for your next move, Chicago might just be the opportunity-packed hub you’ve been waiting for.
What It Means to Be an Owner Operator in Today’s Trucking World
So, what exactly is an owner operator, and why are so many drivers making the switch?
Put simply, an owner operator is a truck driver who owns (or leases) their own rig and runs their business independently—either by contracting with carriers or finding their own loads. Unlike company drivers who are assigned routes and operate company trucks, owner operators get more control over when they drive, where they go, and how much they earn.
But with that freedom comes responsibility.
Being an owner operator means you’re not just a driver—you’re also a business owner. You’re in charge of everything from maintenance and fuel management to bookkeeping and taxes. It’s a big step, but for many drivers, the benefits far outweigh the challenges. You’re building something for yourself, not just punching the clock for someone else.
In a market like Chicago, that independence can really pay off. With so many freight opportunities running through the area, owner operators have a huge advantage when it comes to choosing profitable loads. Whether you want to stay local or go long haul, there’s no shortage of options.
And let’s not forget: when you’re an owner operator, you’re no longer waiting on dispatch to hand you a load. You choose the work that fits your lifestyle—whether that’s maximizing miles and income or carving out more home time.
Is it for everyone? Not necessarily. But if you’re the kind of driver who wants more control, more flexibility, and the chance to grow your own business, becoming an owner operator might be your next smart move.
How Much Can You Make? Owner Operator Pay & Profit Potential
One of the biggest reasons drivers consider owner operator jobs is the potential to earn more—and in a busy freight market like Chicago, that potential is real.
While earnings can vary depending on the type of freight, distance, and whether you’re leased on or operating under your own authority, here’s what many owner operators in the Chicago area can expect.
Typical Owner Operator Earnings
- Gross Weekly Revenue: $5,000 – $8,000
- Monthly Net Income (after expenses): $8,000 – $15,000
- Annual Take-Home: $100,000 – $200,000+
These numbers depend heavily on how efficiently you manage your truck and business. With high freight volume in and around Chicago, many drivers find consistent, profitable loads—but smart planning makes all the difference.
Common Expenses to Expect
- Fuel
- Truck payments (if financing or leasing)
- Insurance (liability, cargo, physical damage)
- Maintenance and repairs
- Permits and registration (IFTA, IRP, DOT)
- Taxes and accounting services
These expenses can take up to 40–50% of your gross revenue. Understanding your break-even point is key.
How to Increase Your Profit
- Focus on high-paying lanes out of Chicago
- Avoid deadhead miles
- Choose reliable freight partners
- Track every expense and adjust your rates accordingly
Owner operator jobs offer the freedom to choose your loads and schedule, but profitability depends on how well you run your operation. Chicago’s busy freight network gives you the opportunity—what you do with it is up to you.
What You Need to Get Started as an Owner Operator in Chicago
Making the move into owner operator jobs is a big step—but it’s one that can open up serious opportunities, especially in a freight-heavy market like Chicago. That said, before you can hit the road under your own name, there are a few key things you’ll need to have in place.
The first and most obvious requirement is a valid Class A CDL. Most trucking companies and brokers working with owner operators prefer drivers with at least a year or two of recent experience, along with a clean driving record. If you’ve already been driving for a while, you’re off to a good start.
Next comes the business side. Becoming an owner operator means you’re not just a driver anymore—you’re a small business owner. That means you’ll need to set up your trucking business legally and obtain the proper operating authority if you plan to run independently. This includes things like a DOT number, motor carrier authority, and filing the appropriate paperwork with both state and federal agencies.
Insurance is another big part of the puzzle. From primary liability to cargo and physical damage coverage, you’ll be responsible for carrying the policies that protect both you and your loads. Some drivers choose to lease onto a carrier to simplify this step, especially when starting out.
Finally, you’ll need to stay compliant with regulations, handle your own bookkeeping, and maintain your truck to pass inspections. It’s more responsibility than driving for a company, but many say the freedom and earning potential are well worth it.
If you’re ready to take ownership of your career, owner operator jobs in Chicago offer a solid path forward—once you’re set up properly.
Also Read: The Truck Driver Shortage: Problems and Solutions
Drive with XXII Century: Opportunities for Owner Operators and Company Drivers
If you’re searching for owner operator jobs in Chicago, XXII Century isn’t just another name in the trucking world—it’s a company that’s built around driver success. Whether you’re an experienced owner operator looking for freedom and flexibility, or a skilled driver ready to join a dependable fleet, XXII Century offers real opportunities on the road.
For owner operators, this is more than just a freight connection—it’s a partnership. XXII Century gives you the independence to run your business your way, backed by support that helps you stay profitable. With access to steady freight, competitive rates, and optional fuel and maintenance programs, you’ll spend less time worrying about overhead and more time earning. Unlike some carriers, they respect that you’re running your own operation—and they treat you like a business partner, not just a number.
The company also hires qualified company drivers looking for reliable truck driving jobs with consistent routes, modern equipment, and a strong team culture. If you’re not quite ready to become an owner operator yet, this is a solid path to gain experience and earn a competitive income.
XXII Century serves the greater Chicago area and surrounding regions, which means there are plenty of local trucking jobs available as well. Whether you prefer staying close to home or hitting long-haul lanes, there’s flexibility here to match your lifestyle.
If you’re ready to level up your career—on your terms—take a closer look at XXII Century. They’re always looking for motivated drivers to join the team, especially those ready to take ownership of their future.
Your Next Move Starts Here
Chicago isn’t just a transportation hub—it’s a city full of opportunity for drivers who are ready to take the next step. Whether you’re exploring owner operator jobs to gain more control over your schedule and earnings, or you’re looking for solid company driving work with a reliable carrier, there’s no shortage of options in this market.
We’ve covered the benefits of running your own rig, what it takes to get started, how much you can earn, and why companies like XXII Century are making it easier than ever for drivers to succeed. From local routes to long hauls, and from new business owners to seasoned pros, there’s a lane for every kind of driver in Chicago.
If you’re serious about growing your trucking career and want to be part of a company that values your work and respects your independence, now’s the time to act.