Chicago is a major economic center with strong demand across finance, logistics, tech, and healthcare. Companies such as United Airlines, Boeing, McDonald’s, and Stripe have deep roots in the city. Jobs in Chicago benefit from a lower cost of living than coastal hubs while still offering access to world-class employers.
826 jobs for The Gainey Agency in Chicago
Illinois has OTR CDL A flatbed driver jobs-1 yr. experience required
NewPosted 21 May 2026Hunt TransportationTRUCK DRIVING JOBS: WE ARE HIRING DRIVERS! We're a Certified Top Pay Carrier and the top 50 percent of our drivers average $93,347 per year. NOW HIRING: Job Description:Drivers who want to see the country are a perfect fit for the Hunt Transportation national OTR fleets. These are our highest mileage fleets and home to our top-earning dr...
Flatbed OTR Class A CDL Driver - $1,094.00 - $2,103.53 per week. Full Benefits
Posted 11 May 2026System TransportJob Description:CDL A OTR Flatbed Driver: $1,094.00 - $2,103.53 per week. Full BenefitsAMERICA PROUD. FLATBED STRONG. DRIVE SYSTEM TRANSPORT!Looking for an exciting driving opportunity in the western region of America? System Transport is hiring experienced CDL-A flatbed truck drivers for regional and OTR routes. As a driver, you will be transporti...
Flatbed OTR Class A CDL Driver - $1,094.00 - $2,103.53 per week. Full Benefits
NewPosted 21 May 2026System TransportJob Description:CDL A OTR Flatbed Driver: $1,094.00 - $2,103.53 per week. Full BenefitsAMERICA PROUD. FLATBED STRONG. DRIVE SYSTEM TRANSPORT!Looking for an exciting driving opportunity in the western region of America? System Transport is hiring experienced CDL-A flatbed truck drivers for regional and OTR routes. As a driver, you will be transporti...
OTR CDL A Driver Home Every Weekend, Dedicated Lanes
Posted 11 May 2026Green Lines Transportation, Inc.Job Description: OTR CDL A Driver Home Every Weekend, Dedicated LanesCall ex. 218 Immediately! These opportunities won t last long! Green Lines Transportation is looking for CDL A Flatbed Drivers. We are busy. We have been Family Owned and Operated for over 30 years. We are one of the top paying carriers in the Industry while maintaining excellen...
Call Smith Today at Job Description: CDL-A OTR TRUCK DRIVER JOBS Must have at least 1 year recent CDL-A OTR Experience Home Weekly on Week Days 48 Hours - Off Either Tuesday & Wednesday or Wednesday & Thursday Come see what it means to have it all at Smith Transport - the best company driver equipment, steady dedicated freight, predictable ...
Job Description: Class A CDL Driver OTR Freight Up To $200,000+ About the Company: Founded in 2008 by Ross Sapir, Roadway Moving is built on the core principles of accountability, kindness, generosity, and dedication. These values drive a culture of excellence, where our people not just our trucks set us apart in a crowded industry. We believe...
12 Days Out CDL A Driver Job -Top 50% average $92,163 / $.61 to $.64 cpm
Posted 11 May 2026Crete Carrier Corporation> TRUCK DRIVING JOBS: WE ARE HIRING DRIVERS! INCREASED DRIVER STARTING PAY AT CRETE CARRIER, INDUSTRY LEADING PAY IS JUST THE BEGINNING Yes, you read that right: with a $0.03 per mile raise for our OTR fleet, with the top 50% of our OTR drivers averaging over $101,000 annually. Need to get through the house more often? We ve raised pay on AL...
12 Days Out CDL A Driver Job -Top 50% average $92,163 / $.61 to $.64 cpm
NewPosted 21 May 2026Crete Carrier Corporation> TRUCK DRIVING JOBS: WE ARE HIRING DRIVERS! INCREASED DRIVER STARTING PAY AT CRETE CARRIER, INDUSTRY LEADING PAY IS JUST THE BEGINNING Yes, you read that right: with a $0.03 per mile raise for our OTR fleet, with the top 50% of our OTR drivers averaging over $101,000 annually. Need to get through the house more often? We ve raised pay on AL...
Hiring CDL-A Truck Drivers PAY THAT DELIVERS - Earn up to $120,000 per year SPECIALIZED FREIGHT, STRONG START - Drivers get a $2,500 sign on bonus PERKS THAT STACK - 100% paid medical premium, paid holidays, bonuses & more Why Drive for E.W. Wylie? Choosing the right carrier is about more than miles and money-it's about respect, support, and lo...
Job Description: CDL A Lease Purchase Driver Apply today or call us at Pay: $2,000.00 - $3,000.00 per week Job description: Join our team based out of our main yard in Chicago, Illinois, and take advantage of this incredible lease-to-own opportunity! With our transparent pay structure and premium trucks, you can focus on your driving career ...
Jobs in Chicago center on finance, manufacturing, food processing, and a rapidly growing tech sector. Boeing, United Airlines, Abbott Laboratories, JPMorgan Chase, and Northwestern Medicine are major employers. Salaries are competitive nationally while the cost of living sits well below New York or San Francisco, making it an attractive market for professionals. The CTA "L" train and Metra commuter rail form one of the country's best public transit networks. Key employment districts include the Loop, River North, Fulton Market, and the growing West Loop tech hub. Chicago is also a major logistics center thanks to O'Hare Airport and its central rail connections.