Independent Contractor Delivery Driver — Chicago

Dragonfly Tech; Chicago (IL); On-site; USD 35,000 - 50,000; Full time

Job summary

Dragonfly is expanding its delivery network in Chicago and is seeking independent contractor drivers (1099). The role offers flexible, on‑demand routes—you choose when you are available, and volume varies by day and client.

To qualify, you need a valid driver’s license and an insured vehicle, a smartphone, and you must be 18+ and eligible to work in the US. This is an independent contractor role, not employment, and no prior delivery experience is required.

Qualifications

• A valid driver's license and an insured vehicle.
• A smartphone.
• 18+ and eligible to work in the US.
• Independent contractor role, not employment. No experience required.

Responsibilities

• Flexible, on-demand delivery routes—you choose when you are available.
• Volume varies by day and client.

Skills

Smartphone

Driver's license

Vehicle insurance

Job description

Independent Contractor Delivery Driver - Chicago

Chicago, United States | Posted on 10/08/2026

Dragonfly was founded with the vision to create a same-day high quality delivery service enabling on-demand and pre-scheduled delivery in every local market across the country.

Job Description

Dragonfly is a delivery platform for restaurants, caterers, bakeries and local businesses. We are adding independent contractor (1099) drivers in the Chicago area.

About the work: flexible, on-demand delivery routes - you choose when you are available. Volume varies by day and client.

What you need:

• A valid driver's license and an insured vehicle
• A smartphone
• 18+ and eligible to work in the US

This is an independent contractor role, not employment. No experience required.