1099 driver jobs in Chicago

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205 1099 driver job listings in United States. Find daily updated positions from leading job boards.


  • Chicago, Illinois, United States RidenRoll Full-time

    Your safety is our top priority!     Company Overview: RidenRoll offers SaaS and Employer Support Services. www.RidenRoll.com is a California-based, for-profit technology platform designed to connect users with ride-hauling drivers and delivery services at competitive prices. We are dedicated to delivering top-notch services, fostering a competitive...


  • Chicago, Illinois, United States Thedrivingdesk Full-time $2,200 - $2,400

    We're hiring experienced Class A CDL Drivers for over-the-road dry van and reefer positions covering all 48 contiguous states. This opportunity offers 100% no-touch freight, assigned late-model equipment, high CPM, and flexible home time based on your preferred schedule. Both solo drivers and established teams are welcome to apply. Pay & Compensation Solo...

  • CDL A Truck Driver

    3 days ago


    Chicago, Illinois, United States Riverside Transport Full-time

    Job DescriptionBefore applying for this role, please read the following information about this opportunity found below.Contracting CDL-A Truck DriversEARN TODAY. OWN TOMORROW - Up to $1,650 weekly take-homePAID TO GET STARTED - $5,000 sign-on bonus + $500 orientation payEASY FREIGHT. EASY WEEKS. - 100% no-touch dry van, 60% drop & hookWhy Drive for Riverside...

  • CDL A Team Drivers

    5 days ago


    Chicago, IL, Cook County, IL; Illinois, United States roadrunner Full-time

    Contracting CDL-A Teams HIGH GROSS. REAL FREEDOM - Up to $12K/week for teams* YOUR BUSINESS, YOUR WAY - Choose your own loads, routes, home time RUN WITH THE BEST - Join as an existing team or start your teams career here Contracting CDL A Team Drivers! Roadrunner is built differently. There are no company drivers, no competing for freight, and no...


  • Chicago, IL, IL, United States MDTV TRANSPORT LLC Full-time $75,000 - $150,000 Contract

    **Home Daily | Monday–Friday | Local & Regional Container Work** MDTV Transport is hiring experienced CDL-A 1099 Company Drivers and Owner-Operators for local and regional container/intermodal work. We run primarily throughout IL, WI, MI, IN and IA, with some OH loads. PAY **1099 Company Drivers** - $75,000–$125,000 per year - Direct deposit every...


  • Chicago, Illinois, United States Truck with Jed Logistics Full-time $2,400 - $2,700

    Are you ready for great OTR position?  Isn't it great to have home time, dry van, reefer, and possible truck selection?  Run Solo or we will even take a Premade Team if you have a partner ready to roll. We have 2024-2027 Volvo's and 2024-2027 Freightliners, loaded with APU, Fridge, Microwave, Inverter and Tablet!   Driver must have 6 months of...

  • CDL A Truck Driver

    5 days ago


    Chicago, IL, Cook County, IL; Illinois, United States riverside transport Full-time

    Contracting CDL-A Truck Drivers EARN TODAY. OWN TOMORROW - Up to $1,650 weekly take-home PAID TO GET STARTED - $5,000 sign-on bonus $500 orientation pay EASY FREIGHT. EASY WEEKS. - 100% no-touch dry van 60% drop & hook Why Drive for Riverside Transport? At Riverside Transport, drivers aren't just numbers on a board - they're part of the family. We...


  • Chicago, Illinois, United States American Logistics Authority Full-time

    OWNER-OPERATOR DRIVERS – ALL TRAILER TYPES (1099 Independent Contractor) Now Contracting Owner-Operators Nationwide We are actively contracting motivated Owner-Operator drivers with their own authority to run consistent freight across multiple trailer types. Our dispatch team brings 30+ years of real-world transportation and logistics experience across...


  • Chicago, Illinois, United States Trucking Talent Solutions Full-time

    SAP Drivers Needed for a 1099 OTR positions. If your on Step 6 we have a variety of positions available. OTR delivering loads throughout the US. These positions are dry van, drop and hook and no touch freight.PAY1099 POSITION Solo70 to 75 CPM Depending on experience2200 to 2500 a week pay3200 Miles plusMinimum 3 weeks out/3 off1099...


  • Chicago, IL, United States Mile 26 LLC Full-time

    CDL A Regional Reefer Truck Driver Job Summary: MILE 26 LLC is seeking hardworking, experienced CDL A Reefer Drivers for Regional routes in the Midwest. If you are willing to work hard, we make it worth your time with a minimum of 2,000 miles guaranteed weekly, great pay, and 99% no-touch freight! Compensation & Perks: $0.90 per mile (Minimum 2,000...

  • 1099 Field Adjuster

    10 hours ago


    Chicago, Illinois, United States CCMS & Associates Full-time

    Join CCMS & Associates!We are answering a call to action to expand our roster - join us as a 1099 Residential or Commercial Field Adjuster!Requirements:·       Minimum 1 year first-party commercial and/or residential property adjusting experience·       Maintain own current estimating software - Xactimate preferred (Cotality a...


  • Chicago, Illinois, United States C3 Trucking Full-time $30 Permanent

    Job Details!Class A Home Daily Drivers out of Elk Grove IL and you must live within 40 miles-NO EXCEPTIONS!THIS IS A 1099 ACCOUNTHome dailyHauling Dry Van$30/hr plus mileage payNo touch freight70% drop n hookRunning Within a 200-400 mile of Chicagoland area - Schedule: Monday to Saturday1200 miles weekly$1900 weekly average Requirements:6 months class a...


  • West Chicago, IL, United States Mile 26 LLC Full-time

    CDL A Regional Reefer Truck Driver Job Summary: MILE 26 LLC is seeking hardworking, experienced CDL A Reefer Drivers for Regional routes in the Midwest. If you are willing to work hard, we make it worth your time with a minimum of 2,000 miles guaranteed weekly, great pay, and 99% no-touch freight! Compensation & Perks: $0.90 per mile (Minimum 2,000...

  • Delivery Driver

    12 hours ago


    Chicago, Illinois, United States Cosi Part-time €30 - €50 Permanent

    Job Overview Così is a quick service restaurant concept delivering sandwiches, fresh salads, heart-warming soups, pizzas and hearty bowls. We’re looking for happy and hardworking people to help us bring our customers a unique Così experience, through the delivery. This is position is part-time typically from 10 am to 2 pm Monday to Friday, and can earn...

  • CDL Driver

    10 hours ago


    Chicago, Illinois, United States Lion Freight Systems Full-time $1,900 - $2,300

    CDL-A Driver Wanted.Pay & Details:Dry Van: 70cpm (all miles paid).On average 3,000+ miles per week.Paid detention, layover, and extra stops.Weekly direct deposit.24/7 dispatch support.1099 position.Based in Chicago, IL.Runs mainly Midwest, South, and Southeast, but we cover all 48 states.Equipment (2020-2027): Volvo, Freightliner, Kenworth, Peterbilt,...

  • CDL A Truck Drivers

    1 week ago


    Chicago, IL, United States Roadrunner Full-time

    Contracting CDL-A Truck Drivers HIGH GROSS. REAL FREEDOM - Up to $12K/week for teams; up to $4K/week solo* YOUR BUSINESS, YOUR WAY - Choose your own loads, routes, home time BETTER BENEFITS, LOWER COST - Health insurance plans available Run with the Best Roadrunner is built differently. There are no company drivers, no competing for freight, and no...


  • Chicago, Illinois, United States Medical Delivery Services Part-time $80 - $100 Contract

    Medical Delivery Driver (Independent Contractor – 1099) Medical Delivery Services is contracting Independent Drivers (1099) for medical delivery routes using your own vehicle. No delivery experience required. Fast onboarding and steady earnings. Compensation $400-$600+/week (based on route volume, miles & availability)Compensation is based on per mile and...

  • CDL A Team Drivers

    1 week ago


    Chicago, IL, United States Roadrunner Full-time

    Contracting CDL-A Teams HIGH GROSS. REAL FREEDOM - Up to $12K/week for teams* YOUR BUSINESS, YOUR WAY - Choose your own loads, routes, home time RUN WITH THE BEST - Join as an existing team or start your teams career here Contracting CDL A Team Drivers! Roadrunner is built differently. There are no company drivers, no competing for freight, and no...

  • Hazmat / Tanker Driver

    12 hours ago


    Chicago, Illinois, United States Lion Freight Systems Full-time $2,000 - $3,000

    $2,000-$3,000 | OTR Dry Van & Reefer CDL Drivers WantedJob details:Dry van & Reefer trailers.70-75cpm or 27% of the gross.New automatic trucks (2020-2027).1099 position with weekly direct deposit.2-3 weeks out.24/7 dispatch & driver support.Requirements:At least 2 years of CDL Class A experience.Valid Medical Card.Apply today - start tomorrow! Hiring...


  • Chicago, Illinois, United States RidenRoll Full-time

    Your safety is our top priority. www.ridenroll.com Let’s Roll Download the App and submit your documents to become a Driver through the app Grow with RidenRoll; Your Success is our Success!! Share the App with your Friends and Family   Apple Store: https://apps.apple.com/us/app/ridenroll/id6446574531 Google...