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Flex Driver Jobs in Chicago, IL (NOW HIRING)

Tucker Freight Lines

CDL-A Truck Driver

Chicago, IL · On-site

$1.6K/wk

Up to $1,650 per Week* - Local & Flex Routes Comprehensive Benefits Available What's In It For You? * Drivers average $1,200-$1,650 per week* * Local Base Pay: Earn $25 per hour * Local Flex Pay:

Tucker Freight Lines

CDL-A Truck Driver

Streamwood, IL · On-site

$1.6K/wk

Up to $1,650 per Week* - Local & Flex Routes Comprehensive Benefits Available What's In It For You? * Drivers average $1,200-$1,650 per week* * Local Base Pay: Earn $25 per hour * Local Flex Pay:

Tucker Freight Lines

CDL-A Truck Driver

Chicago, IL · On-site

$1.6K/wk

Up to $1,650 per Week* - Local & Flex Routes Comprehensive Benefits Available What's In It For You? * Drivers average $1,200-$1,650 per week* * Local Base Pay: Earn $25 per hour * Local Flex Pay:

Tucker Freight Lines

CDL-A Truck Driver

Chicago, IL · On-site

$1.6K/wk

Up to $1,650 per Week* - Local & Flex Routes Comprehensive Benefits Available What's In It For You? * Drivers average $1,200-$1,650 per week* * Local Base Pay: Earn $25 per hour * Local Flex Pay:

Tucker Freight Lines

CDL-A Truck Driver

Orland Park, IL · On-site

$1.6K/wk

Up to $1,650 per Week* - Local & Flex Routes Comprehensive Benefits Available What's In It For You? * Drivers average $1,200-$1,650 per week* * Local Base Pay: Earn $25 per hour * Local Flex Pay:

Tucker Freight Lines

CDL-A Truck Driver

Evanston, IL · On-site

$1.6K/wk

Up to $1,650 per Week* - Local & Flex Routes Comprehensive Benefits Available What's In It For You? * Drivers average $1,200-$1,650 per week* * Local Base Pay: Earn $25 per hour * Local Flex Pay:

Tucker Freight Lines

CDL-A Truck Driver

Frankfort, IL · On-site

$1.6K/wk

Up to $1,650 per Week* - Local & Flex Routes Comprehensive Benefits Available What's In It For You? * Drivers average $1,200-$1,650 per week* * Local Base Pay: Earn $25 per hour * Local Flex Pay:

Tucker Freight Lines

CDL-A Truck Driver

Chicago, IL · On-site

$1.6K/wk

Up to $1,650 per Week* - Local & Flex Routes Comprehensive Benefits Available What's In It For You? * Drivers average $1,200-$1,650 per week* * Local Base Pay: Earn $25 per hour * Local Flex Pay:

Tucker Freight Lines

CDL-A Truck Driver

Hammond, IN · On-site

$1.6K/wk

Up to $1,650 per Week* - Local & Flex Routes Comprehensive Benefits Available What's In It For You? * Drivers average $1,200-$1,650 per week* * Local Base Pay: Earn $25 per hour * Local Flex Pay:

Tucker Freight Lines

CDL-A Truck Driver

Chicago, IL · On-site

$1.6K/wk

Up to $1,650 per Week* - Local & Flex Routes Comprehensive Benefits Available What's In It For You? * Drivers average $1,200-$1,650 per week* * Local Base Pay: Earn $25 per hour * Local Flex Pay:

Tucker Freight Lines

CDL-A Truck Driver

Chicago, IL · On-site

$1.6K/wk

Up to $1,650 per Week* - Local & Flex Routes Comprehensive Benefits Available What's In It For You? * Drivers average $1,200-$1,650 per week* * Local Base Pay: Earn $25 per hour * Local Flex Pay:

Tucker Freight Lines

CDL-A Truck Driver

Chicago, IL · On-site

$1.6K/wk

Up to $1,650 per Week* - Local & Flex Routes Comprehensive Benefits Available What's In It For You? * Drivers average $1,200-$1,650 per week* * Local Base Pay: Earn $25 per hour * Local Flex Pay:

Tucker Freight Lines

CDL-A Truck Driver

Lansing, IL · On-site

$1.6K/wk

Up to $1,650 per Week* - Local & Flex Routes Comprehensive Benefits Available What's In It For You? * Drivers average $1,200-$1,650 per week* * Local Base Pay: Earn $25 per hour * Local Flex Pay:

Tucker Freight Lines

CDL-A Truck Driver

Lisle, IL · On-site

$1.6K/wk

Up to $1,650 per Week* - Local & Flex Routes Comprehensive Benefits Available What's In It For You? * Drivers average $1,200-$1,650 per week* * Local Base Pay: Earn $25 per hour * Local Flex Pay:

Tucker Freight Lines

CDL-A Truck Driver

Chicago, IL · On-site

$1.6K/wk

Up to $1,650 per Week* - Local & Flex Routes Comprehensive Benefits Available What's In It For You? * Drivers average $1,200-$1,650 per week* * Local Base Pay: Earn $25 per hour * Local Flex Pay:

Tucker Freight Lines

CDL-A Truck Driver

Batavia, IL · On-site

$1.6K/wk

Up to $1,650 per Week* - Local & Flex Routes Comprehensive Benefits Available What's In It For You? * Drivers average $1,200-$1,650 per week* * Local Base Pay: Earn $25 per hour * Local Flex Pay:

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Flex Driver information

See Chicago, IL salary details

$5

$16

$23

How much do flex driver jobs pay per hour?

As of Aug 19, 2026, the average hourly pay for flex driver in Chicago, IL is $16.78, according to ZipRecruiter salary data. Most workers in this role earn between $14.86 and $17.84 per hour, depending on experience, location, and employer.

What is a flex driver?

Flex Drivers are independent contractors who deliver packages for companies like Amazon using their own vehicles. They sign up through a platform, such as Amazon Flex, and choose delivery blocks that fit their schedule. Flex Drivers are responsible for picking up packages from designated locations and delivering them to customers' addresses. This job offers flexible hours and can be a good source of supplemental income, but drivers are responsible for expenses like gas and vehicle maintenance.

What skills and qualifications are needed to be a flex driver?

To thrive as a Flex Driver, you need a valid driver's license, a clean driving record, and a sound knowledge of local routes and delivery protocols. Familiarity with GPS navigation apps, route optimization tools, and mobile delivery platforms is typically required. Excellent time management, customer service, and problem-solving skills help drivers adapt to changing schedules and deliver a positive customer experience. These competencies ensure timely, safe, and efficient deliveries while maintaining customer satisfaction in a flexible, fast-paced work environment.

What challenges do flex drivers face and how can they be managed?

Flex Drivers often face challenges such as navigating unfamiliar routes, handling tight delivery schedules, and adapting to varying package loads. To manage these effectively, it’s helpful to use GPS navigation tools, plan routes ahead of time, and maintain clear communication with dispatch or support teams. Staying organized and keeping a positive attitude also contribute to efficient deliveries and a smoother workday.

What is the difference between Flex Driver vs Delivery Driver?

AspectFlex DriverDelivery Driver
CredentialsValid driver's license, clean driving recordValid driver's license, sometimes specific certifications for certain vehicles
Work EnvironmentFlexible hours, various locations, often on-demandScheduled routes, fixed hours, specific delivery areas
Employer & IndustryGig economy platforms, logistics companiesRestaurants, retail stores, courier services

Flex Drivers typically work on-demand with flexible hours, often for gig platforms, while Delivery Drivers usually follow scheduled routes for specific companies. Both roles require a valid driver's license and involve driving in urban or suburban areas. The main difference lies in flexibility and employment structure, with Flex Drivers enjoying more adaptable schedules compared to the more routine-based Delivery Drivers.

How do I become a flex driver?

To become a flex driver, you typically need a valid driver's license, a clean driving record, and sometimes a background check. Flex drivers often use a mobile app to accept shifts and must be able to work flexible hours, with some companies requiring specific vehicle types or insurance coverage.

What do flex drivers get paid?

Flex drivers typically earn an hourly wage that varies by location and company, often ranging from minimum wage up to $20 or more per hour. They may also receive additional pay for peak hours, tips, or bonuses, depending on the employer and schedule flexibility. Compensation can include benefits if classified as employees rather than independent contractors.

What are the most commonly searched types of Driver jobs in Chicago, IL?

The most popular types of Driver jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Flex Driver jobs?

Cities near Chicago, IL with the most Flex Driver job openings:

Flex Driver jobs near you
Infographic showing various Flex Driver job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 70% Full Time, 27% Part Time, and 2% Contract. Highlights an 97% Physical, 1% Hybrid, and 2% Remote job distribution, with an average salary of $34,909 per year, or $16.8 per hour.

OTR CDL A Flex Truck Driver | $104,000 per Year | Paid Weekly | Chicago, IL

Ruan

Chicago, IL • On-site

$104K/yr

Full-time

Re-posted 25 days ago

Job description

About the Job
Ruan is hiring a Class A CDL Flex driver for our dedicated LKQ customer, domicile is out of Janesville, WI. Our flex drivers never have to worry about not having enough work available, because we'll send you to where extra help is needed! These drivers will travel to various customers & operations around the United States and support the locations that are in need of extra coverage. For more information, please call our Recruiting Hotline at (800) 879-7826 .
Pay
Get paid weekly!
  • $104,000 average annual
  • $2,000 average weekly
  • $40 per hour straight time

Schedule
Be over-the-road for five weeks at a time and enjoy a consecutive week of home time! Schedules and start times vary on the location a driver is supporting. Guaranteed a 50-hour workweek.
Equipment
Operate different types of equipment based on the customer you are assisting. Mix of no-touch freight, driver assist, unloading, and tarping. Tank endorsement and Hazmat endorsement required. Ruan will help obtain Hazmat within 60 days of hire. Forklift experience preferred but will train. Real ID and U.S. Passport are required.
Benefits
Ruan appreciates your commitment to our success. We're equally committed to providing you with competitive, affordable health and wellness benefits to help you take care of yourself and your family. View all benefits information here .
Why Ruan?
People First, Safety Focus, 90+ Years Strong
Minimum Requirements
  • Must be at least 22 years or older
  • No more than three moving violations in the past three years (some restrictions apply)
  • No more than one DOT recordable preventable accident in the last three years
  • With the Department of Transportation's Drug and Alcohol Clearinghouse in effect, all applicants must create a profile at fmcsa.dot.gov before being hired
  • 9 months of tractor-trailer experience within the past three years
  • Must be able to read and speak the English language sufficiently to converse with the general public, understand highway traffic signs and signals in English, respond to official inquiries, and make entries on reports and records
  • Additional qualifications will apply

EOE | Dedicated to Diversity
Ruan logo

About Ruan

Sourced by ZipRecruiter

Ruan, based in Des Moines, IA, US, is a prominent name in the transportation and supply chain solutions industry. Established in 1932 by John Ruan, the company began with a single truck and has since transformed into a nationwide transportation conglomerate. Ruan mainly offers integrated supply chain solutions encompassing Dedicated Contract Transportation, Managed Transportation, Value-added Warehousing, and Brokerage Support Services. Spearheading the industry for nearly nine decades, Ruan carries forward its founder's legacy of unwavering commitment to safety, customer satisfaction, quality, and integrity, which are deeply embedded in its core values.

Industry

Transportation and warehousing

Company size

1,001 - 5,000 Employees

Headquarters location

Des Moines, IA, US

Year founded

1932

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