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Weekend 1099 Driver Jobs in Chicago, IL (NOW HIRING)

RidenRoll

1099 Contractor Drivers

Chicago, IL · On-site

1099 Contractor Drivers Your safety is our top priority! Company Overview: RidenRoll offers SaaS ... Valid US driver's license * You have an iPhone or Android smartphone. * Proof of residency in your ...

RidenRoll

1099 Contractor Drivers

Chicago, IL · On-site

Valid US driver's license * You have an iPhone or Android smartphone. * Proof of residency in your ... W-9 form for 1099 contractors * Comfortable using GPS navigation apps. Vehicle Requirements: * Less ...

Backyard Products

54 - 1099 Delivery Driver

Elgin, IL · On-site

$16.75 - $20.75/hr

The 1099 Delivery Driver will be responsible for ensuring timely delivery of goods to predetermined customers on specific routes, reviewing orders prior to delivery, unloading trucks, and providing ...

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Weekend 1099 Driver information

See Chicago, IL salary details

$5

$16

$26

How much do weekend 1099 driver jobs pay per hour?

As of Sep 7, 2026, the average hourly pay for weekend 1099 driver in Chicago, IL is $16.76, according to ZipRecruiter salary data. Most workers in this role earn between $14.62 and $17.07 per hour, depending on experience, location, and employer.

What is the difference between Weekend 1099 Driver vs Part-Time Delivery Driver?

AspectWeekend 1099 DriverPart-Time Delivery Driver
CredentialsDriver's license, background checkDriver's license, background check
Work EnvironmentFlexible, independent, on-demandFlexible, on-demand, delivery-focused
Employer TypeIndependent contractor, gig platformsEmployers or gig platforms
Work SchedulePrimarily weekends, flexible hoursVaries, often weekends or evenings

Weekend 1099 Drivers and Part-Time Delivery Drivers both require a valid driver's license and background check. They operate in flexible, on-demand environments, often working weekends or evenings. The main difference is that Weekend 1099 Drivers typically work independently through gig platforms, while Part-Time Delivery Drivers may be employed or contracted by companies. Both roles suit those seeking flexible schedules in the delivery industry.

What are the most commonly searched types of 1099 Driver jobs in Chicago, IL?

The most popular types of 1099 Driver jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Weekend 1099 Driver jobs?

Cities near Chicago, IL with the most Weekend 1099 Driver job openings:

Weekend 1099 Driver jobs near you
Infographic showing various Weekend 1099 Driver job openings in Chicago, IL as of August 2026, with employment types broken down into 33% Full Time, and 67% Part Time. Highlights an 100% In-person job distribution, with an average salary of $34,861 per year, or $16.8 per hour.

CDL Class A driver - Solo OTR - New Kenworth Sleeper

Strange Trip, Inc.

Schaumburg, IL • On-site

Full-time

Re-posted yesterday

Job description

CDL Class A OTR Driver

Location

  • OTR. Tractor may be parked at home or nearby FedEx yard during home time.

Employment Type

  • 1099 Driver | Full-Time OTR Solo

Position Overview

  • This is a full-time, over-the-road solo driving position operating under FedEx authority, with a dedicated dispatcher providing consistent, year-round, high-mileage freight.
  • Willing to obtain Hazmat endorsement within 120 days of hire.
  • This role is ideal for drivers seeking high miles, reliable pay, and new, well-maintained equipment. We value drivers who take pride in professionalism, communication, and delivering exceptional service.

Equipment

  • New 2026 Kenworth T680 tractor
  • Maintained under a strict, consistent preventative maintenance program
  • We operate only safe, clean, and well-maintained vehicles

Requirements

  • Valid CDL Class A license
  • Willing to obtain hazmat endorsement within 120 days of start date
  • Minimum 6 months tractor-trailer experience in the last 2 years, or 1 year in the last 5 years
  • Willing and able to stay out 2 weeks at a time (home time requests always accommodated)
  • Clean MVR and criminal background
  • Excellent communication skills
  • Commitment to safety, reliabiltiy, customer service, and equipment care
  • Ability to follow FedEx procedures and security standards

Run Details

  • Over-the-road dry van freight
  • Dedicated dispatch through FedEx Custom Critical
  • Nationwide lanes with consistent, year-round freight

Compensation

  • $1500 sign on bonus
  • Solo pay $0.70 cents per mile
  • Guaranteed minimum of 1750 miles per week regardless of miles driven if driver was available Sunday thru Saturday (7 days)
  • Weekly direct deposit
  • Paid monthly online safety training
  • Company covers fuel, tolls, repairs, maintenance, insurance, etc.

Why Drive for Strange Trip?

  • Strange Trip Inc. is a professional, family-owned FedEx contractor known for strong dispatch support, transparent pay, and a driver-first culture. We invest in new equipment and build long-term partnerships with our drivers.
  • Apply today and become part of the Strange Trip team.

Apply