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Established Transportation Company – Operating Since 2007 Exceptional opportunity to acquire a well-established transportation company with nearly 20 years of operating history. Founded in 2007, the... Businesses Franchises Brokers Loading... Profitable Transportation Company | $1.2M Cash Flow | Fleet Included Cook County, IL Asking Price:$5,950,000 Cash Flow (SDE):$1,200,000 EBITDA:$1,000,000 Gross Revenue:$5,000,000 Established:2007 Profitable Transportation Company | $1.2M Cash Flow | Fleet Included Business Description Nearly 20 Years in Business with Strong Customer Relationships Established Transportation Company – Operating Since 2007 Exceptional opportunity to acquire a well-established transportation company with nearly 20 years of operating history. Founded in 2007, the business has built a strong reputation for reliability, customer service, and operational excellence within the transportation and logistics industry. The company generates over $5 million in annual revenue and operates with an experienced infrastructure designed to support continued growth. Included in the sale are 17 Freightliner Cascadia tractors and 20 trailers, all owned free and clear, providing significant hard-asset value and immediate operating capacity. The business benefits from long-standing customer relationships, proven operating systems, experienced personnel, and an established presence in the marketplace. The company is positioned for future expansion through additional fleet utilization, customer growth, dedicated freight opportunities, and strategic market expansion. Ad#:2515231 Detailed Information Furniture, Fixtures, & Equipment (FF&E): $10,000 Included in asking price Employees: 23 (2 Full-time, 1 Part-time, 20 Contractors) Facilities: The company operates an established transportation business with a fleet consisting of 17 paid-off Freightliner Cascadia tractors and 20 paid-off trailers. The fleet is maintained in active service and included in the sale. The business also includes operating authority, customer relationships, goodwill, established operating systems, and other transportation-related equipment and assets necessary for ongoing operations. Key Assets Included: • 17 Freightliner Cascadia tractors (owned free and clear) • 20 trailers (owned free and clear) • Operating authority and business goodwill • Established customer relationships • Dispatch and operational systems • Trade name and business records • Transportation-related equipment and tools Estimated fleet asset value exceeds $2,000,000. Competition: Established transportation company operating since 2007 in a large and essential industry. Strong customer relationships, repeat business, and a debt-free fleet provide a competitive advantage. Significant opportunities exist to expand operations, increase fleet utilization, and grow revenue through additional customers and dedicated freight contracts. Growth & Expansion: Significant growth opportunities exist through fleet expansion, driver recruitment, increased equipment utilization, dedicated freight contracts, and expansion of existing customer relationships. The company has established systems, a debt-free fleet, and nearly 20 years of operating history that provide a strong platform for future growth. Support & Training: Seller will provide up to 90 days of transition assistance, including customer introductions, operations training, dispatch procedures, compliance guidance, and business handoff support. Reason for Selling: Owner is pursuing other business and investment opportunities Business Location Location: Cook County, IL Real Estate: Leased Building SF: 1,500 Rent: $1,500.00 Demographic Information for Cook County Area Household Income Population Age Population Trend Population by Race/Ethnicity BizBuySell EDGE Real Estate Insights Monthly Lease Rate per SF Sale Price per SF BizBuySell EDGE Metro Area Scores Walk Score Transit Score BizBuySell EDGE Financial Benchmarks for Illinois Trucking Companies Gross Revenue Benchmarks Cash Flow (SDE) Benchmarks EBITDA Benchmarks BizBuySell EDGE Listing Statistics Saved This Listing Listing Last Updated Appeared in Search Listing Detail Views BizBuySell EDGE Know the True Market Value Before You Make an Offer Get valuation data to negotiate with confidence. Get a Valuation Report Business Listed By: Alex Bayrev Phone Number 847-687-2429 Voice only (no SMS) Ad#:2515231 The information in this listing has been provided by the business seller or representative stated above. BizBuySell has no stake in the sale of this business, has not independently verified any of the information about the business, and assumes no responsibility for its accuracy or completeness. Read BizBuySell's Terms of Use before responding to any ad. Learn how to avoid scams. Contact Form Full Name* Enter a valid Full Name Phone Number Enter Phone Number Email Address* Enter Email Address Optional Message Yes, send me the Buyer Newsletter for popular businesses, tips, & email promotions. Learn how to secure financing and get prequalified before buying a business. Send Message By clicking the button, you agree to BizBuySell’s Terms of Use and Privacy Notice Business Listed By: Alex Bayrev Phone Number 847-687-2429 Your request has been sent. What Happens Next? is reviewing your details. A representative will reach out soon to discuss your options. Expect a response in 1-2 business days. Report an issue with this listing Similar Listings Trucking Companies for Sale All Businesses for Sale in Cook County Nationwide Niche Logistics Business with Strong Cash Flow DuPage County, IL Asking: $7,000,000 Triple Threat: Logistics, Brokerage & Warehousing at $10M+ Per YR Kane County, IL Asking: $6,118,455 6 Trucking Company - MC and Assets Des Plaines, IL Asking: $500,000 InXpress Franchise Opportunity Cash Required: $50,000 ©2026 CoStar Group Send Message Listing Shared via Email a6301374279843840.cdn.optimizely.com a6301374279843840.cdn.optimizely.com is blocked This page has been blocked by an extension Try disabling your extensions. 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Why we like it
- Hard asset protection with $2M+ in debt-free equipment provides significant downside floor. The 17 Freightliner Cascadias and 20 trailers alone represent roughly one-third of the asking price, and commercial trucking equipment holds value better than most business assets during downturns.
- Transportation is recession-resilient with sticky B2B relationships spanning nearly 20 years. Freight movement remains essential even during economic slowdowns, and established customer relationships in logistics create switching costs that protect revenue streams.
- Chicago market positioning offers access to one of the largest freight hubs in North America. Cook County location provides proximity to intermodal facilities, distribution centers, and manufacturing corridors that generate consistent freight demand.
- Owner-operator model with 20 contractor drivers reduces labor liability while maintaining operational leverage. This structure allows for easier scaling and reduces the fixed cost burden compared to employee-heavy transportation models.
How to improve it
- Audit the contractor vs employee classification immediately to ensure DOT compliance and avoid potential labor reclassification liability. Review all driver agreements, payment structures, and operational control to confirm proper independent contractor status.
- Implement dynamic pricing and customer profitability analysis to identify underperforming routes and relationships. Many trucking companies operate on legacy pricing that hasn't kept pace with fuel, insurance, and equipment costs.
- Expand dedicated contract opportunities with existing customers to reduce spot market exposure and improve margin predictability. Long-term dedicated routes provide better utilization and pricing power than transactional freight.
- Install fleet telematics and driver scorecards to improve fuel efficiency and reduce insurance costs. Modern fleet management technology can reduce fuel consumption by 8-15% and lower insurance premiums through demonstrated safety improvements.
- Evaluate equipment utilization rates and consider subleasing underutilized assets or expanding the contractor driver network. With 17 tractors and 20 trailers, there may be opportunities to optimize asset deployment or grow revenue per unit.
Diligence notes
- Reconcile the revenue discrepancy between the $5.95M headline number and $5M detailed figure, and verify the actual cash flow calculation. The SDE vs EBITDA vs Cash Flow terminology is used inconsistently and needs clarification.
- Review DOT compliance history including safety ratings, inspection records, and any violations or fines. Transportation companies face significant regulatory risk and compliance issues can impact operating authority and insurance costs.
- Analyze customer concentration and contract terms to understand revenue stability and pricing mechanisms. Determine what percentage comes from spot vs contract freight and identify any customer concentration risks.
- Verify equipment condition, maintenance records, and remaining useful life of the fleet assets. Request recent appraisals and maintenance logs to confirm the claimed $2M+ asset value and understand upcoming capital requirements.