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.
835 jobs for The Gainey Agency in Chicago
Driver Contractors With or Without Own Tow Vehicle Local Regional OTR and Next Day Pay
Posted 14 May 2026TruckMoversJob Description: Driver Contractors With or W/O Own Tow Vehicle Great Pay - Next Day! Local, Regional & OTR Class A or B! Be your own boss! Company Profile: TruckMovers drivers are independent contractors and have the freedom to operate on their own schedule. You choose the types of loads you deliver. Your investment in equipment is minimal a...
Overview: Imagine a career that truly takes you places, where you get to travel and meet new people every day along the journey. For 100 years, our Greyhound Drivers have been the heart and soul of our company, serving the transportation needs of communities across the nation. Do you enjoy meeting new people and have a passion for safety and the c...
Illinois has OTR CDL A flatbed driver jobs-1 yr. experience required
Posted 11 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...
CDL-A OTR Company Driver - Affordable Benefits Package + $98,280 Per Year Per Driver
Posted 11 May 2026ForwardJob Description:Searching for a company that values team drivers and rewards your miles? Forward is actively hiring team Class A OTR Company Drivers in your area! When driving with Forward, you can expect consistent miles, industry-leading benefits and a competitive per-mile rate - paid to you based on your team's total miles. What makes this oppo...
APPLY ONLINE BELOW OR CALL TO IMMEDIATELY SPEAK WITH OUR TEAM Job Description:Sorry, Visa / sponsorship not available.Company Drivers $1,500 Weekly Guarantee / Potential to make MORE! - $5,000 Sign On Bonus - Most runs will have you home daily - $2,500 Driver Retention Bonus / Paid Quarterly - Most runs within 300 miles of the terminal - Insura...
CDL A Driver: Earn $101,176 yr with 1 yr or more driving experience!
NewPosted 16 May 2026Crete CarrierJob Description: 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...
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...
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.