Owner Operator Jobs in Chicago

Chicago
Owner operator job opportunities in Chicago - Professional CDL driver with semi-trucks

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.

Available Owner Operator Jobs in Chicago, Illinois

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Owner Operator - $6,000-$9,000 - Modena Freight

Chicago, Illinois $6,500 - $10,000 a week Owner Operator
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

Chicago, Illinois $2,500 - $3,500 a week Owner Operator
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

Chicago, Illinois $5,000 - $10,000 a week Owner Operator
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

Chicago, Illinois $8,000 - $14,000 a week Owner Operator
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

Chicago, Illinois $4,000 - $6,500 a week Owner Operator
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

Chicago, Illinois $6,000 - $8,000 a week Owner Operator
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

Chicago, Illinois $6,000 - $8,000 a week Owner Operator
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

Chicago, Illinois $2,000 - $3,000 a week Owner Operator
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 Job Locations in Chicago, Illinois

Discover owner operator opportunities throughout the Chicago metropolitan area and surrounding regions.

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