CDL Jobs in Chicago, Illinois
Find truck driving opportunities in Chicago – Local, Regional, OTR & Owner Operator positions available.
150+
Active CDL Jobs
$70K+
Average Driver Salary
25+
Local Trucking Companies
$200K+
Owner Operator Potential
Chicago offers exceptional opportunities for CDL drivers as the transportation hub of the Midwest and one of America's largest freight centers. Located at the intersection of major interstate highways including I-94, I-90, and I-55, Chicago provides unparalleled access to shipping routes connecting the East and West coasts. The city's extensive transportation network creates massive demand for local, regional, and long-haul drivers serving O'Hare International Airport, the Port of Chicago, and countless distribution facilities. Chicago CDL drivers benefit from competitive wages, with average salaries ranging from $68,000 to $100,000 annually, plus comprehensive benefits packages. The city's diverse economy supports various freight types, from manufacturing goods to agricultural products and e-commerce deliveries, ensuring consistent job availability year-round. With major distribution centers for Amazon, UPS, FedEx, and countless other companies, Chicago remains the premier destination for professional truck drivers seeking stable, high-paying careers.
CDL Job Types in Chicago, Illinois
-
Local CDL Jobs in Chicago
Home daily local routes. Predictable schedules.
- Home every night
- Predictable schedules
- Typical pay: $55k–$75k
- Local delivery routes
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Regional CDL Jobs in Chicago
Multi-state routes; home weekly with solid benefits.
- Home weekly
- Regional lanes
- Typical pay: $65k–$85k
- Consistent freight
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OTR CDL Jobs in Chicago
Long-haul opportunities with mileage pay.
- Nationwide routes
- High mileage
- Typical pay: $75k–$95k
- Travel the country
-
Owner Operator Jobs in Chicago
Be your own boss with strong earning potential.
- Business ownership
- Flexible schedules
- $90k+ potential
- Lease-purchase options
Latest CDL Job Listings in Chicago,Illinois
Explore Regional, OTR, Owner Operator & Local Jobs in Chicago,Illinois
Regional Class A-Truck Driver
The Sherwin-Williams Company
Start on a rewarding career as a Regional Driver with Sherwin-Williams in Chicago, IL. Enjoy job security, competitive benefits, and a supportive work environment.
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CDL-A Truck Driver - Regional OTR - No Touch Freight
G&D Integrated
Drive for G&D Integrated in Joliet, IL, with weekly home time, choice of pay structure, and a supportive team environment. Earn up to $100,000 yearly with full benefits and advancement opportunities.
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CDL-A Truck Driver, Regional
Online Transport
Online Transport is hiring CDL-A Truck Drivers in multiple regions, offering competitive pay, benefits, and a supportive work environment. Join us for a fulfilling career on the road.
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CDL A Truck Driver, Home Weekly Regional
HMD Trucking Inc
Become a core part of HMD's fleet, operating Peterbilt 579 trucks with competitive pay, home time, and benefits. Join us to drive your career forward.
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CL A Dedicated Regional Home Weekly- Riders & Pets Welcome Full Benefits
The Wick Transport
Hiring Class A drivers for a regional role with dedicated tractor, competitive pay, and comprehensive benefits package. Home weekly in multiple states.
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Regional Class A CDL Intermodal Company Solo Driver - Home Daily
DriveLine Solutions
Exciting regional opportunity for Class A CDL solo drivers. Earn $1,200 - $1,500 weekly with no-touch freight. Must have 2 years experience and live near Chicago.
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Regional Tanker and Van Truck Driver
Pullman Logistics LLC
Pullman Logistics seeks local tanker and van drivers in Chicago. Earn up to $80,000 annually with family-owned values, diverse workforce, and strong benefits package.
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Class A CDL Drivers Needed - Regional Dedicated | Home Weekly | No Touch
Trucking Pro
Become a Local Intermodal driver in Chicago, IL, with consistent home time, $1,500 weekly pay, and growth opportunities. Apply today for immediate start!
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Regional CDL Class A Truck Driver
JRayl Transport Inc
Embark on a fulfilling career as a Regional/OTR CDL Class A Truck Driver at JRayl Transport. Competitive pay, benefits, and diverse trucking routes for experienced drivers.
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Class A-CDL Regional Driver
Trucker Time Xpress LLC
Join our team as a regional truck driver operating in Iowa, Wisconsin, and Indiana. Enjoy $1400-$1600 weekly pay, home time, and newer trucks. Must reside within 50 miles of Chicago.
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OWNER OPERATOR - $6,000-$9,000
Modena Freight
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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Class A CDL Owner Operator
Laurelle Empire LLC
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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CDL Class A Owner Operator
Optimus Dispatching Services, LLC
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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HIRING CDL A OWNER OPERATORS 88% OF GROSS/*FREE TRAILER*
One star capital
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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CDL Class A Owner Operator - OTR/Regional $4,000 - $6,500
Fleet Haven, LLC
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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CDL A Flatbed Owner Operator
Beemac Trucking
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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CDL A Truck Driver - Owner Operator - Flatbed Steel Coil
JLE Industries
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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Owner Operator
ALLSTATES EXPRESS INC
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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Owner Operator Truck Driver
Flex Transport inc
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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Class A Owner Operator Truck Driver for Dedicated Dry Van to Chicago
Dry Creek Logistics
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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Class A Owner Operator Truck Driver for Consistent Dry Van out of Chicago
Freight MVMT LLC
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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OWNER OPERATORS WITH MULTIPLE TRUCKS (REGIONAL AND OTR ONLY): 6% DISPATCH FEE!
Wheel Trans Logistics
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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Dispatch Company for Qualified OTR Dry Van Flatbed Reefer Owner Operator(Check Out Description!!)
C.H.O.A L.L.C
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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OWNER OPERATOR - $6,000 - $9,000
J&M Enterprises
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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Rands Trucking is Hiring OTR Owner Operators, Top Earners Average $223,000 Annually
RANDS TRUCKING
Launch your future in Chicago with RANDS TRUCKING! Enjoy an impressive salary of $225,000/year while tapping into a vibrant contractor community that thrives in this market. Benefit from a generous package designed for owner-operators, providing access to invaluable business resources and diverse freight opportunities. Build your independent business locally and take advantage of the unique advantages this area offers. Your journey toward success begins here!
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Seeking CDL Class A Owner Operators
Fox Freight, Inc.
Your career starts in Chicago, where owner operators can thrive with Fox Freight, Inc. In this bustling market, enjoy the advantages of a vibrant contractor community and endless freight opportunities. Earning up to $8,000.00 per week, you’ll also benefit from a generous package that supports your independent business. The resources available locally empower you to take charge of your career while connecting with a network dedicated to your success.
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Owner/Operator
Merx Global
Build your career from Melrose Park with Merx Global, where owner-operators can earn up to $6,500 per week. This market offers a vibrant contractor community, providing unparalleled resources for independent businesses. Enjoy a generous package designed to support your success, along with a complete benefits suite that empowers you to thrive. With various freight opportunities available in the area, you’re positioned to build a rewarding future in the heart of Illinois.
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CDL class A Owner Operators for Amazon Loads Drop and hook, !!! Get started in 1 day, $8-10k gross
Reserve Truck Lines LTD
Excel in the Chicago market by partnering with Reserve Truck Lines LTD. This area is teeming with freight opportunities, making it an ideal place to build your independent business. Owner-operators can enjoy a superior compensation package that averages around $6,000.00 per week, alongside essential medical benefits. With a robust contractor community and access to invaluable business resources, this market offers the perfect environment for success in the trucking industry.
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Owner/Operator/Fleet Owner
Kerr Relocation LLC
Build your career from Chicago with Kerr Relocation LLC, where local drivers earn an impressive $12,000.00 per week. Enjoy routes that allow you to serve businesses in the area while being home every night, fostering community connections. The generous package includes health insurance, dental, and vision coverage, ensuring you and your family are well taken care of. Embrace the opportunity to thrive locally while navigating familiar roads and building lasting relationships.
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CDL A Owner Operator – Keep 90% of Load Pay
Victory Truck & Trailer Repair
Excel in the Chicago market while driving your career with Victory Truck & Trailer Repair. Locally, owner operators find exceptional opportunities with a generous package that includes a competitive salary of $3,500.00 per week. Leverage the area’s thriving contractor community and abundant freight opportunities to build a successful independent business. Enjoy a complete benefits suite designed to support your goals while enjoying the unique advantages of this vibrant market.
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Owner-Operator Box Truck Driver
Ambufreight
Drive success from Chicago with Ambufreight, where owner-operator CDL positions offer unparalleled opportunities in this vibrant market. Enjoy an impressive salary of $3,000.00 per week while tapping into vital routes and resources that only a metropolitan hub can provide. Build your independent business within a thriving contractor community, all backed by a generous package that supports your entrepreneurial journey. Take advantage of the countless freight opportunities this area has to offer.
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Intermodal Owner Operator - Redbird Carriers
Redbird Carriers
Discover advantages in La Grange for owner operator CDL positions with Redbird Carriers. This area boasts a vibrant contractor community and a strategic location, offering excellent freight opportunities. Enjoy a generous package with an impressive salary of $3,500 per week, complemented by a complete benefits suite designed for your success. Here, you’ll find the resources necessary to build and thrive as an independent business owner.
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STRAIGHT TRUCK OWNER OPERATOR
Bullet Express Freight
Excel in the Elk Grove Village market with Bullet Express Freight, where owner-operators are valued for their independence and expertise. Benefit from competitive pay at $50.00 per hour while enjoying a generous package designed to support your business growth. The city offers a vibrant contractor community and robust freight opportunities, allowing you to thrive in a supportive environment. This area is ideal for those committed to building a successful independent business.
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Owner Operator - Tanker Driver
Altom Transport, Inc.
Experience opportunity in Chicago with Altom Transport, Inc. As an owner-operator in this area, you’ll benefit from a thriving contractor community and extensive freight opportunities that support your independent business. Enjoy competitive compensation along with a generous package that includes a comprehensive benefits suite designed to enhance your operations. With robust resources and support locally, you’ll be positioned to thrive in this dynamic market. Embrace the potential that awaits you in Illinois.
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Owner Operator CDL A OTR
FREIGHTX LLC
Choose FREIGHTX LLC in Chicago, where booming local demand and a dense network of routes facilitate efficient transportation for Owner Operator CDL A OTR professionals. This prime location ensures continuous freight availability, optimizing both loading and unloading operations. Enjoy home-time advantages while earning $6,000 - $9,000 weekly. Benefit from our competitive fuel card and discounts, all while leveraging proximity to major highways, enhancing your transport efficiency and profitability.
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Class A OTR Owner Operator - Chicago
US Expediting & Logistics LLC
Chicago's dynamic logistics hub provides Class A OTR Owner Operators at US Expediting & Logistics LLC with unparalleled opportunities, thanks to its proximity to key interstate highways and thriving freight corridors. Operating here means efficient route density and consistent demand, enhancing profitability with competitive compensation at $1.20 per mile. The location facilitates frequent returns, balancing work and home life, with added advantages like fuel discounts boosting overall earnings. A compelling base for success in the Midwest and beyond.
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TRUCK DRIVER / OTR / DEDICATED LANES
Road Runners America Logistics LLC
Drive with Road Runners America Logistics LLC in Chicago for competitive weekly earnings of $2,200 to $3,500. Chicago's bustling transportation hub ensures consistent freight loads and optimal route density, enhancing your efficiency and profitability. Enjoy strategic proximity to major interstates, which provides seamless access and improved time management on dedicated lanes. Benefit from our fuel card and referral program, tailored to support owner operators who seek stability in a thriving market.
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Maximize Your Income: CDL A Owner Operators Keep 90% Gross!
Victory Truck & Trailer Repair
Thriving in Chicago with Victory Truck & Trailer Repair means accessing dense freight corridors that enhance route efficiency and maximize earnings, with owner operators earning $2,500 - $3,500 weekly. Situated at the crux of major expressways, Chicago provides streamlined access to lucrative hauls, ensuring swift turnover and minimized downtime. Beyond top pay, benefit from amenities like our passenger ride-along and pet program, blending lucrative work with comfort and flexibility right in the heart of the Midwest logistics hub.
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Owner-Operator Box Truck
P & J CARRIERS INC
Start your journey as an Owner-Operator Box Truck driver with P & J CARRIERS INC in Chicago, where the bustling transportation hub offers unparalleled opportunities. With significant freight availability due to its strategic location near major interstates, Chicago ensures dense routes for optimized earnings. Enhance your career with a competitive salary range of $5,500 - $7,500 weekly while benefiting from a fuel card perk. The city's vibrant logistics network supports your success and maximizes efficiency.
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Owner Operators with 24-26' Box Trucks
Hurdle 2 Success
Strategically positioned in Chicago, Hurdle 2 Success offers owner operators with 24-26' box trucks competitive weekly earnings of $3,400 - $4,700. The city’s extensive network of highways, such as I-90 and I-94, facilitates efficient freight movements and ensures ample opportunities thanks to high local demand. Enjoy the advantage of dense route availability while maintaining better home-time balance, making it an ideal location for committed professionals seeking growth in the logistics sector.
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CDL Class A OWNER OPERATOR Flatbed | 80% PAID TO YOU
KK Transport
Drive your success with KK Transport in Chicago, where the strategic advantage of being a major freight hub significantly boosts earnings. Command a lucrative salary between $286,000 and $390,000 annually as you leverage the ample freight availability and dense route networks in this bustling city. Enjoy the perks of efficient route planning, ensuring more home time and operational efficiency, while our comprehensive benefits, including a passenger ride-along program and health insurance, support your professional journey.
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CDL Truck Driver
Harmony logistics llc
Embrace the thriving logistics scene as a CDL Truck Driver with Harmony logistics llc in Chicago, IL 60607, where local demand fuels steady freight availability. The city’s strategic location offers access to major interstate systems, ensuring efficient route density for optimal operations. Benefit from competitive earnings of $5,700 - $6,500 weekly, alongside perks like a fuel card and comprehensive insurance options. Join a network designed for success, maximizing both your work and home-life balance.
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Box Truck Owner Operator
H8 Trucking
Join H8 Trucking as a Box Truck Owner Operator in the bustling city of Chicago, IL 60618, where strategic location meets high freight demand. This role benefits from the city's extensive network of major highways and terminals, ensuring efficient routes and frequent assignments. With earnings of $4,000 to $5,500 weekly, drivers enjoy the lucrative opportunities provided by Chicago's vibrant economy. Enjoy favorable home-time thanks to dense commercial routes within the region, enhancing both professional and personal life.
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Sleeper Owner Operators | Drop & Hook | Fast Start
Priority Freight LLC
Thrive with Priority Freight LLC in Chicago, where owner operators benefit from the city's robust logistics network and immediate access to major interstates like I-90 and I-94. With competitive earnings ranging from $8,000 to $12,000 weekly, drivers encounter optimal route density enhancing efficiency. The combination of drop and hook convenience and Priority Freight's strategic terminal locations ensures reduced downtime. Enjoy perks including a passenger ride along program, fuel card, and substantial fuel discounts, setting the stage for success.
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Local Class A drivers needed
Semi Fleet Inc
Join our local CDL driving team and enjoy being home daily while earning $1,200-$1,800 weekly. We're seeking experienced CDL Class A drivers for local routes within 350 miles, with opportunities for multiple daily runs. Perfect for drivers who want consistent local work with full-time employment, on-site mechanical support, and 24-hour dispatch assistance. Clean driving record required with weekend availability.
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