Owner Operator Jobs In Chicago, Illinois
Chicago
Chicago's strategic location as America's transportation hub makes it one of the most lucrative markets for owner operators. With access to major interstates I-80, I-90, I-94, and I-55, plus proximity to countless distribution centers and manufacturing facilities, Chicago offers consistent freight opportunities year-round.
The Windy City's diverse economy drives steady demand for trucking services across industries - from automotive parts to food distribution. Owner operators in Chicago benefit from short haul opportunities to Milwaukee, Indianapolis, and Detroit, as well as long-haul routes to both coasts.
With O'Hare International Airport and multiple rail yards creating constant freight movement, Chicago owner operators enjoy minimal deadhead miles and maximum earning potential. The city's truck-friendly infrastructure and numerous truck stops make it an ideal base for independent contractors looking to maximize their weekly revenue.
Job Listings
OWNER OPERATOR - $6,000-$9,000
Modena Freight
Expanding trucking company seeks owner operators for regional routes. Earn $6,000-$10,000 weekly gross income with steady loads, no waiting, and benefits including fuel card and trailer programs.
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Class A CDL Owner Operator
Laurelle Empire LLC
Laurelle Empire, a reputable and inclusive employer, offers a chance to grow professionally with opportunities to become a driver trainer after one year of service.
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CDL Class A Owner Operator
Optimus Dispatching Services, LLC
Optimus Dispatching is known for its commitment to simplifying trucking business operations and ensuring client satisfaction. Join us for career growth opportunities, a stellar company reputation, and professional development.
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HIRING CDL A OWNER OPERATORS 88% OF GROSS/*FREE TRAILER*
One star capital
Our company in Naperville, IL offers 24/7 support, career growth opportunities, and a strong reputation in the industry. With a referral program and safety equipment provided, you can thrive in a professional environment.
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CDL Class A Owner Operator - OTR/Regional $4,000 - $6,500
Fleet Haven, LLC
Become part of a prominent dispatch service known for providing superior service and competitive rates. Take advantage of career growth opportunities, professional development, and a strong company reputation.
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CDL A Flatbed Owner Operator
Beemac Trucking
Beemac Trucking, a top 20 Flatbed Carrier in the US, is seeking Owner Operators. With a 40-year history, employee ownership, and 24/7 support, drivers can grow their careers with a reputable company.
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CDL A Truck Driver - Owner Operator - Flatbed Steel Coil
JLE Industries
Join our established transportation company as Class A commercial driver with competitive salary, comprehensive benefits package, consistent regional routes, and opportunities for career advancement and professional growth.
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Owner Operator
ALLSTATES EXPRESS INC
Allstates Express is known for its dedication to owner-operators' success, offering opportunities for career growth, professional development, and a strong company reputation in the transportation industry.
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Owner Operator Truck Driver
Flex Transport inc
Join a reputable company offering career growth and professional opportunities. Rent a semi-truck for $1000 weekly and earn up to $9,000 in gross. Perfect for owner-operators, solo, or team drivers.
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Class A Owner Operator Truck Driver for Dedicated Dry Van to Chicago
Dry Creek Logistics
Experience career growth and professional opportunities with our reputable company. Benefit from a fuel card, pet rider program, and various supplemental pay options. Join our team and thrive in the transportation industry.
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Class A Owner Operator Truck Driver for Consistent Dry Van out of Chicago
Freight MVMT LLC
Join a reputable company in Chicago, IL offering career growth opportunities for Class A CDL Owner Operators. Enjoy flexible schedules, national fuel discounts, and a supportive work environment.
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OWNER OPERATORS WITH MULTIPLE TRUCKS (REGIONAL AND OTR ONLY): 6% DISPATCH FEE!
Wheel Trans Logistics
Wheel Trans Logistics offers a chance for career growth and professional development. With dedicated routes and various job types, drivers can maximize their earnings and reputation in the industry.
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Dispatch Company for Qualified OTR Dry Van Flatbed Reefer Owner Operator(Check Out Description!!)
C.H.O.A L.L.C
CHOA Global Inc. in NYC offers a chance to partner with a reputable company focused on driver success. Grow your career with a team dedicated to rejecting industry failure rates.
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OWNER OPERATOR - $6,000 - $9,000
J&M Enterprises
Our company has a strong reputation for providing regional and OTR operations without idle time. With the opportunity for career growth and professional development, you can count on support from Jordan at 601-270-6530.
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Rands Trucking is Hiring OTR Owner Operators, Top Earners Average $223,000 Annually
RANDS TRUCKING
Launch your future in Chicago with RANDS TRUCKING! Enjoy an impressive salary of $225,000/year while tapping into a vibrant contractor community that thrives in this market. Benefit from a generous package designed for owner-operators, providing access to invaluable business resources and diverse freight opportunities. Build your independent business locally and take advantage of the unique advantages this area offers. Your journey toward success begins here!
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Seeking CDL Class A Owner Operators
Fox Freight, Inc.
Your career starts in Chicago, where owner operators can thrive with Fox Freight, Inc. In this bustling market, enjoy the advantages of a vibrant contractor community and endless freight opportunities. Earning up to $8,000.00 per week, you’ll also benefit from a generous package that supports your independent business. The resources available locally empower you to take charge of your career while connecting with a network dedicated to your success.
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Owner/Operator
Merx Global
Build your career from Melrose Park with Merx Global, where owner-operators can earn up to $6,500 per week. This market offers a vibrant contractor community, providing unparalleled resources for independent businesses. Enjoy a generous package designed to support your success, along with a complete benefits suite that empowers you to thrive. With various freight opportunities available in the area, you’re positioned to build a rewarding future in the heart of Illinois.
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CDL class A Owner Operators for Amazon Loads Drop and hook, !!! Get started in 1 day, $8-10k gross
Reserve Truck Lines LTD
Excel in the Chicago market by partnering with Reserve Truck Lines LTD. This area is teeming with freight opportunities, making it an ideal place to build your independent business. Owner-operators can enjoy a superior compensation package that averages around $6,000.00 per week, alongside essential medical benefits. With a robust contractor community and access to invaluable business resources, this market offers the perfect environment for success in the trucking industry.
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Owner/Operator/Fleet Owner
Kerr Relocation LLC
Build your career from Chicago with Kerr Relocation LLC, where local drivers earn an impressive $12,000.00 per week. Enjoy routes that allow you to serve businesses in the area while being home every night, fostering community connections. The generous package includes health insurance, dental, and vision coverage, ensuring you and your family are well taken care of. Embrace the opportunity to thrive locally while navigating familiar roads and building lasting relationships.
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CDL A Owner Operator – Keep 90% of Load Pay
Victory Truck & Trailer Repair
Excel in the Chicago market while driving your career with Victory Truck & Trailer Repair. Locally, owner operators find exceptional opportunities with a generous package that includes a competitive salary of $3,500.00 per week. Leverage the area’s thriving contractor community and abundant freight opportunities to build a successful independent business. Enjoy a complete benefits suite designed to support your goals while enjoying the unique advantages of this vibrant market.
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Owner-Operator Box Truck Driver
Ambufreight
Drive success from Chicago with Ambufreight, where owner-operator CDL positions offer unparalleled opportunities in this vibrant market. Enjoy an impressive salary of $3,000.00 per week while tapping into vital routes and resources that only a metropolitan hub can provide. Build your independent business within a thriving contractor community, all backed by a generous package that supports your entrepreneurial journey. Take advantage of the countless freight opportunities this area has to offer.
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Intermodal Owner Operator - Redbird Carriers
Redbird Carriers
Discover advantages in La Grange for owner operator CDL positions with Redbird Carriers. This area boasts a vibrant contractor community and a strategic location, offering excellent freight opportunities. Enjoy a generous package with an impressive salary of $3,500 per week, complemented by a complete benefits suite designed for your success. Here, you’ll find the resources necessary to build and thrive as an independent business owner.
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STRAIGHT TRUCK OWNER OPERATOR
Bullet Express Freight
Excel in the Elk Grove Village market with Bullet Express Freight, where owner-operators are valued for their independence and expertise. Benefit from competitive pay at $50.00 per hour while enjoying a generous package designed to support your business growth. The city offers a vibrant contractor community and robust freight opportunities, allowing you to thrive in a supportive environment. This area is ideal for those committed to building a successful independent business.
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Owner Operator - Tanker Driver
Altom Transport, Inc.
Experience opportunity in Chicago with Altom Transport, Inc. As an owner-operator in this area, you’ll benefit from a thriving contractor community and extensive freight opportunities that support your independent business. Enjoy competitive compensation along with a generous package that includes a comprehensive benefits suite designed to enhance your operations. With robust resources and support locally, you’ll be positioned to thrive in this dynamic market. Embrace the potential that awaits you in Illinois.
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Owner Operator Job Locations in Chicago, Illinois
Discover owner operator opportunities throughout the Chicago metropolitan area and surrounding regions.