Transportation & Logistics Businesses for Sale in Chicago, IL

This trucking and logistics operation is built around recurring routes and long-term client relationships, producing predictable service demand. Buyers may value the stable operating model, diverse customer base, and established reputation across the Midwest.

This asset-based transportation business includes equipment and active operations, which can reduce startup friction for a new owner. It may appeal to a buyer seeking a logistics company in Illinois with working trucks and an operating structure already in place.

This Illinois trucking and logistics company has operated for nearly two decades, generating over $5M in annual revenue and approximately $1M in annual SDE with a fully owned fleet of 17 tractors and 20 trailers transferred free and clear. The business benefits from long-standing customer relationships, experienced personnel, and a proven operating infrastructure that supports continued growth. At a $5.95M asking price with significant hard-asset value embedded, this is a compelling acquisition for a logistics operator or strategic buyer seeking an established transportation platform in the Chicago region.

This Illinois-based NEMT company operates five days per week, transporting a diverse client base including Medicaid recipients, veterans, dialysis patients, and rehabilitation clients across the Chicago metro area and surrounding regions. The company is credentialed with all Illinois Medicaid managed care organizations and has established relationships serving federal transportation programs. It generates $285,000 in annual cash flow on a $900,000 asking price, with structural demand tailwinds driven by an aging population and expanding Medicaid coverage.

This nationwide first-and-final-mile logistics company operates a non-asset model with a fleet of 70 commercial trucks — 90% fully owned — and an established customer base that provides consistent cash flow across multiple U.S. markets. All existing company loans are structured to be satisfied at closing, delivering a clean balance sheet to the incoming owner. At a $1.189 million SDE on a $7 million asking price, the business offers an acquirer a scaled logistics platform with proven operational infrastructure and low capital expenditure requirements relative to asset-heavy transportation peers.

This specialized trucking company transports fuel and bulk liquids for commercial clients in the Midwest and Mid-Atlantic regions, generating approximately $4.2 million in annual revenue with $407,000 in EBITDA. The business operates with a fully staffed 24/7 dispatch operation, experienced general manager, and a fleet of leased tractors and tanker trailers, enabling strong management infrastructure without requiring hands-on owner involvement. Recurring commercial contracts and dedicated operational support staff create a scalable foundation for a new owner seeking a logistics platform.

This family-owned trucking company offers a clean operating authority from 2014 along with a fleet of trucks and trailers, established broker relationships, and a retiring owner willing to support a transition period. With $280K in annual discretionary earnings on a $525K asking price, the business offers a strong return for an owner-operator or an established carrier looking to expand fleet and authority. The asset-backed nature of the deal and long-standing broker relationships reduce ramp-up time for a qualified buyer.