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Weekend 1099 Delivery Jobs in Skokie, IL (NOW HIRING)

The RedWagon Delivers

Delivery Driver

Chicago, IL · On-site

$15 - $100/hr

As a 1099 contractor, you will manage your own schedule and operate as an independent business partner. Deliveries typically take 30 minutes and are most frequent between 9 AM and 2 PM, though routes ...

The RedWagon Delivers

Delivery Driver

Chicago, IL · On-site

$15 - $100/hr

As a 1099 contractor, you will manage your own schedule and operate as an independent business partner. Deliveries typically take 30 minutes and are most frequent between 9 AM and 2 PM, though routes ...

The RedWagon Delivers

Delivery Driver

Oak Park, IL

$15 - $100/hr

As a 1099 contractor, you will manage your own schedule and operate as an independent business partner. Deliveries typically take 30 minutes and are most frequent between 9 AM and 2 PM, though routes ...

The RedWagon Delivers

Delivery Driver

Northbrook, IL

$15 - $100/hr

As a 1099 contractor, you will manage your own schedule and operate as an independent business partner. Deliveries typically take 30 minutes and are most frequent between 9 AM and 2 PM, though routes ...

Urban Delivery

Delivery Driver

Chicago, IL · On-site

$16/hr

Dinner (5pm-11pm) Weekends: Lunch(10am-5pm), dinner(5pm-10pm). Applicants who apply must be able to work one or two shifts on Saturday or Sunday. Urban Delivery Just Deliver Food! Unlike other ...

Rapid Delivery Solutions

Delivery Driver

Palatine, IL

$22.75 - $25.75/hr

Flexible Shifts: 10-hr/day shifts with weekend availability Compensation & Benefits for Delivery Drivers: $22.75-$25.75/Hr Starting Pay - Plus Bonus Opportunities! * Bonus Pay $$$ (for Delivery ...

Rapid Delivery Solutions

Delivery Driver

Palatine, IL · On-site

$22.75 - $25.75/hr

Flexible Shifts: 10-hr/day shifts with weekend availability Compensation & Benefits for Delivery Drivers: $22.75-$25.75/Hr Starting Pay - Plus Bonus Opportunities! * Bonus Pay $$$ (for Delivery ...

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Weekend 1099 Delivery information

See Skokie, IL salary details

$7

$17

$24

How much do weekend 1099 delivery jobs pay per hour?

As of May 28, 2026, the average hourly pay for weekend 1099 delivery in Skokie, IL is $17.62, according to ZipRecruiter salary data. Most workers in this role earn between $15.38 and $19.28 per hour, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as a Weekend 1099 Delivery driver, and why are they important?

To excel as a Weekend 1099 Delivery driver, you generally need a valid driver’s license, a clean driving record, and reliable transportation. Familiarity with GPS navigation systems, route optimization apps, and sometimes smartphone delivery platforms is typically required. Strong time management, customer service orientation, and the ability to work independently help drivers stand out in this role. These skills ensure timely, accurate deliveries and positive customer experiences, which are critical for success and repeat business.

What are some common challenges faced by Weekend 1099 Delivery drivers, and how can they be managed?

Weekend 1099 Delivery drivers often encounter challenges such as unpredictable traffic patterns, increased delivery volumes during peak hours, and the need to efficiently navigate unfamiliar routes. Since drivers are independent contractors, managing time and planning routes effectively is crucial to maximize earnings and complete deliveries on schedule. Building strong communication with dispatchers and using route optimization tools can help mitigate these issues and ensure a smooth delivery experience.

What are Weekend 1099 Delivery jobs?

Weekend 1099 Delivery jobs are positions where individuals work as independent contractors (not employees) to deliver goods, packages, or food during weekends. The '1099' refers to the IRS tax form used to report earnings for independent contractors in the United States. These roles offer flexibility, allowing workers to choose their hours and routes, but they are responsible for their own taxes and expenses. Common employers include courier services, food delivery apps, and retail companies. Weekend work is popular for those seeking extra income or flexible schedules.

What is the difference between Weekend 1099 Delivery vs Weekend 1099 Package Handler?

AspectWeekend 1099 DeliveryWeekend 1099 Package Handler
CredentialsValid driver’s license, vehicle insuranceNone specific, physical ability required
Work EnvironmentOn the road, customer homes, businessesWarehouse, sorting facilities
Employer & IndustryDelivery service companies, logisticsShipping carriers, fulfillment centers

Weekend 1099 Delivery involves driving and delivering packages directly to customers, requiring a vehicle and driving credentials. In contrast, Weekend 1099 Package Handlers work in warehouses, focusing on sorting and preparing packages for shipment. Both roles are gig-based, independent contractor positions within the logistics industry, but they differ in work environment and daily tasks.

What are popular job titles related to Weekend 1099 Delivery jobs in Skokie, IL? For Weekend 1099 Delivery jobs in Skokie, IL, the most frequently searched job titles are:
What job categories do people searching Weekend 1099 Delivery jobs in Skokie, IL look for? The top searched job categories for Weekend 1099 Delivery jobs in Skokie, IL are:
What cities near Skokie, IL are hiring for Weekend 1099 Delivery jobs? Cities near Skokie, IL with the most Weekend 1099 Delivery job openings:
Weekend 1099 Delivery jobs near you
Infographic showing various Weekend 1099 Delivery job openings in Skokie, IL as of May 2026, with employment types broken down into 64% Full Time, 18% Part Time, and 18% Contract. Highlights an 91% In-person, and 9% Remote job distribution, with an average salary of $36,651 per year, or $17.6 per hour.

Delivery Driver

The RedWagon Delivers

Chicago, IL • On-site

$15 - $100/hr

Part-time

Posted 5 days ago

Job description

The RedWagon Delivers is seeking reliable, motivated independent contractors to join our delivery team. Our ideal candidate has experience with platforms such as DoorDash, Grubhub, or Uber Eats, and understands how partnering with RedWagon can increase overall earnings. As a 1099 contractor, you will manage your own schedule and operate as an independent business partner.

Deliveries typically take 30 minutes and are most frequent between 9 AM and 2 PM, though routes are available from 6 AM to 9 PM, seven days a week. Your availability directly determines your earning potential. Compensation is per delivery, not hourly. Top earners regularly make between $50 and $200+ per day.

We have jobs available in and around the Chicago area:

  • Chicago
  • Downers Grove
  • Elk Grove Village
  • Homewood
  • Munster
  • Oak Brook
  • Oak Park
  • Rosemont
  • Skokie
  • Stone Park
  • Villa Park

Apply directly on our site: https://www.workstream.us/j/cfd04ead/the-redwagon-delivers/chicago-52527/delivery-driver-a8cc6568?referer_source=https%3A%2F%2Fhr.workstream.us%2F

Qualifications
  • Minimum age of 21
  • Valid U.S. driver's license
  • Smartphone with navigation capability
  • Reliable personal vehicle (van or truck not required)
  • Strong communication and problem-solving skills
  • Excellent attention to detail and ability to follow directions

If onboarded, you must provide your own delivery equipment, including catering bags (23x13x15) and a collapsible cart, wagon, or hand truck. These items are required to meet client standards.

Responsibilities
  • Pick up and deliver food or other items promptly and professionally
  • Transport orders safely and maintain quality during delivery
  • Set up orders at customer locations when requested (light setup only)
  • Accept deliveries across a range of pay levels
  • Represent The RedWagon Delivers with professionalism in appearance and attitude
  • Maintain exceptional customer service standards on every delivery

The RedWagon Delivers is an expert logistics company that specializes in delivering catering, office lunches, alcohol, and small parcel courier services for high-value clients with complex delivery requirements.

Education:{"credentialcategory":"high school","@type":"EducationalOccupationalCredential"}Employment Type: PART_TIME

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