OTR Trucking Jobs In Chicago,Illinois

Chicago
OTR CDL jobs in Chicago

Chicago, Illinois stands as one of the most important OTR trucking hubs in the United States. Known as the crossroads of America’s freight network, OTR truck driving jobs in Chicago provide unmatched opportunities for steady miles, premium freight rates, and reliable long-haul routes connecting every major region of the country.

Carriers based in the Chicago area offer consistent coast-to-coast runs, competitive pay packages, and comprehensive benefits for Class A CDL drivers. With major interstates like I-55, I-80, and I-90 intersecting here, OTR drivers can count on efficient routing and continuous demand from national shippers and logistics companies.

OTR truck drivers in Chicago enjoy the perfect balance of top earnings, dependable freight, and professional growth. Join one of the many trusted fleets headquartered in Illinois and take your trucking career to the next level with high-mileage opportunities that keep America moving.

Featured Opportunities

⭐ FEATURED

Empire National

Based in Chicago, IL

26FT Box Truck Owners
$4,000 - $8,000 a week Owner Operator
✓ Regional & OTR Routes ✓ Fuel discount ✓ No Forced Dispatch ✓ Weekly Settlements
Apply now →
⭐ FEATURED

TRANSGEORGIA LLC

Based in Chicago, IL

Owner Operators Needed – Cargo vans, sprinters & Large Box Trucks
$5,811 - $6,405 a week Owner Operator
✓ Consistent Work Next-Day Pay ✓ No Forced Dispatch ✓ Referral program Apply now →

Available OTR Jobs in Chicago, Illinois

Search by company name, benefits, or job features

OTR flatbed Conestoga driver up to 75 CPM

Benchmark Transportation Inc

Chicago, Illinois $2,000 - $3,000 a week OTR – Long Haul
Excel in the Westchester market with Benchmark Transportation Inc, where empowering owner-operators is a priority. This area offers a robust contractor community and abundant freight opportunities, allowing you to thrive and build your independent business. Enjoy competitive compensation alongside a generous package that includes paid vacation and medical coverage. With resources tailored to support your success, this market is ideal for those looking to make their mark locally.
View Job Details

OTR Truck Driver Class A

TRX EXPRESS INC

Chicago, Illinois $2,000 - $3,000 a week OTR – Long Haul
Your career starts in Crest Hill, where TRX EXPRESS INC is seeking dedicated CDL drivers. As a major transportation hub with excellent highway access, this area provides an ideal home base for your routes. Enjoy competitive compensation along with a generous package designed to support you on and off the road. Embrace the opportunity to thrive in a community that values its drivers and offers a welcoming environment for professional growth.
View Job Details

Owner-operator independent truck driver

Tiger Trans Group LLC

Chicago, Illinois $2,000 - $3,000 a week OTR – Long Haul
Drive success from Chicago with Tiger Trans Group LLC! Enjoy an exceptional earning potential of $3,000.00 per week while tapping into a thriving market rich with freight opportunities. Our contractor community is designed to support your independent business, providing the resources you need to thrive. Enjoy a generous package that ensures you have the tools necessary for long-term success in this dynamic area. Embrace the possibilities and drive your future forward!
View Job Details

CDL A Truck Driver - $1250 orientation pay

Central Oregon Truck Company

Chicago, Illinois Up to $127,000 a year OTR – Long Haul
Join the team in South Holland with Central Oregon Truck Company, where your driving career can thrive! This area serves as a strategic transportation hub, offering excellent highway access that facilitates efficient routes across the region. With an impressive salary of $127,000 per year, drivers enjoy a generous package that includes health, dental, and vision insurance. Locally, you'll find a supportive community that values the contributions of hardworking professionals in the trucking industry.
View Job Details

OTR Truck Driving Jobs Locations in Chicago, Illinois

Discover OTR CDL jobs in Chicago, Illinois and across nationwide routes.

OTR Truck Driving Jobs in Other Illinois Cities

Other Trucking Job Types in Chicago, Illinois

Local (Home-Daily) Jobs in Chicago Explore ALL CDL Jobs in Illinois Regional Jobs in Chicago Owner Operator Jobs in Chicago

OTR Truck Driving Jobs by State

OTR Jobs in Texas OTR Jobs in California OTR Jobs in Florida OTR Jobs in Ohio OTR Jobs in Pennsylvania OTR Jobs in Georgia OTR Jobs in Illinois OTR Jobs in North Carolina OTR Jobs in Tennessee OTR Jobs in Michigan

Browse More OTR Truck Driving Jobs

Looking for your next long-haul opportunity? Explore hundreds of verified OTR truck driving positions nationwide and find your ideal route today.

View All OTR Jobs