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

Chicago Illinois US
USD 8000 WEEK
Modena Freight

Modena Freight

Chicago, Illinois $6,500 - $10,000 a week Owner Operator Posted: January 15, 2025
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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Chicago Illinois US
USD 8000 WEEK
Laurelle Empire LLC

Laurelle Empire LLC

Chicago, Illinois $2,500 - $3,500 a week Owner Operator Posted: January 15, 2025
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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Chicago Illinois US
USD 8000 WEEK
Optimus Dispatching Services, LLC

Optimus Dispatching Services, LLC

Chicago, Illinois $5,000 - $10,000 a week Owner Operator Posted: January 15, 2025
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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Chicago Illinois US
USD 8000 WEEK
One star capital

One star capital

Chicago, Illinois $8,000 - $14,000 a week Owner Operator Posted: January 15, 2025
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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Chicago Illinois US
USD 8000 WEEK
Fleet Haven, LLC

Fleet Haven, LLC

Chicago, Illinois $4,000 - $6,500 a week Owner Operator Posted: January 15, 2025
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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Chicago Illinois US
USD 8000 WEEK
Beemac Trucking

Beemac Trucking

Chicago, Illinois $6,000 - $8,000 a week Owner Operator Posted: January 15, 2025
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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Chicago Illinois US
USD 8000 WEEK
JLE Industries

JLE Industries

Chicago, Illinois $6,000 - $8,000 a week Owner Operator Posted: January 15, 2025
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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Chicago Illinois US
USD 8000 WEEK
ALLSTATES EXPRESS INC

ALLSTATES EXPRESS INC

Chicago, Illinois $2,000 - $3,000 a week Owner Operator Posted: January 15, 2025
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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Chicago Illinois US
USD 8000 WEEK
Flex Transport inc

Flex Transport inc

Chicago, Illinois $5,899 - $6,990 a week Owner Operator Posted: January 15, 2025
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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Chicago Illinois US
USD 8000 WEEK
Dry Creek Logistics

Dry Creek Logistics

Chicago, Illinois $5,800 - $6,500 a week Owner Operator Posted: January 15, 2025
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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Chicago Illinois US
USD 8000 WEEK
Freight MVMT LLC

Freight MVMT LLC

Chicago, Illinois $5,000 - $6,000 a week Owner Operator Posted: January 15, 2025
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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Chicago Illinois US
USD 8000 WEEK
Wheel Trans Logistics

Wheel Trans Logistics

Chicago, Illinois $3,000 - $8,000 a week Owner Operator Posted: January 15, 2025
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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Chicago Illinois US
USD 8000 WEEK
C.H.O.A L.L.C

C.H.O.A L.L.C

Chicago, Illinois $6,200 - $12,000 a week Owner Operator Posted: January 15, 2025
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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Chicago Illinois US
USD 8000 WEEK
J&M Enterprises

J&M Enterprises

Chicago, Illinois $6,000 - $9,000 a week Owner Operator Posted: January 15, 2025
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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Owner Operator Job Locations in Chicago, Illinois

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

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