10 Best Trucking Companies To Work for in Chicago, IL

• Salary range: $50,000-$70,000
• Routes: interstate
• Paid CDL training: true
• Ongoing training: Paid CDL training
• Power units: 15
• Drivers: 12
• Revenue: $4,695,000
• Miles driven: 627,531 (2023)

• Glassdoor: 3.8 / 5
• Indeed: 4.1 / 5

Keller Trucking Co, Inc. (DOT: 143868) has no founding date listed in the provided records and is based in Waukegan, Illinois. The carrier hauls chemicals, general freight, intermodal containers, metal sheets/coils/rolls, paper products, and other cargo using services that include dry van, flatbed, reefer, full truckload, less-than-truckload, partial truckload, and dedicated routes. They hire CDL drivers for local, regional, OTR, team, dedicated, reefer, flatbed, and FTL roles, and they also offer paid CDL training and a new driver program.

Keller Trucking offers a well-rounded driver benefits package that includes health, dental, vision, life, and disability insurance; paid time off; a 401(k) retirement plan; direct deposit; pay advances; safety bonuses; driver referral bonuses; sign-on bonuses; guaranteed home time; ongoing training; fuel cards; uniforms; and deadhead, detention, and layover compensation. They also allow riders or pets, which can be a meaningful perk for over-the-road drivers.

Employee ratings are generally positive, with a 4.1 score on Indeed and a 3.8 score on Glassdoor. Positive feedback commonly points to dependable pay, solid benefits, supportive training, newer equipment, and a family-oriented work environment. Negative feedback tends to focus on the challenges common in trucking, including scheduling demands, time away from home, workload variability, and occasional communication or dispatch frustrations.

• Salary range: $55,000-$65,000
• Routes: interstate
• Ongoing training: Paid CDL training
• Power units: 269
• Drivers: 220
• Miles driven: 9,189,341 (2024)

• Glassdoor: 2.8 / 5
• Indeed: 4.5 / 5

Area Transportation (DOT: 213341) is the DBA name for Odyssey Specialized Logistics LLC, an active interstate carrier based in Chesterton, Indiana; its founding date is not listed in the available records. The company hauls general freight, beverages, building materials, construction materials, grain/feed/hay, intermodal containers, logs, poles, beams, lumber, large machinery, metal sheets/coils/rolls, paper products, and utility-related cargo.

Area Transportation hires a wide range of drivers, including local, regional, OTR, dedicated, owner-operator, hazmat, specialized, reefer, LTL, parcel, full-truckload, and tanker drivers. Driver benefits include a sign-on bonus, direct deposit, health, dental, vision, and life insurance, paid time off, a 401(k), safety bonuses, per diem payments, guaranteed home time, flexible scheduling, referral bonuses, detention/layover/deadhead compensation, ongoing training, fuel cards, uniforms, and roadside assistance programs.

Area Transportation has an Indeed rating of 4.5 and a Glassdoor rating of 2.8. Positive employee feedback most often appears to center on benefits, pay-related incentives, steady work, and home-time programs, while negative feedback is more likely to mention management communication, work-life balance, scheduling consistency, or operational organization.

• Salary range: $50,000-$75,000
• Routes: interstate
• Ongoing training: Paid CDL training
• Tuition reimbursement: true
• Power units: 2645
• Drivers: 3381
• Revenue: $4,112
• Miles driven: 203,000,000 (2024)

HUB Group (DOT: 801828) is an active interstate carrier based in Oak Brook, Illinois; the provided records do not list a specific founding date. Operating as Hub Group Dedicated LLC, the company hauls general freight, intermodal containers, refrigerated food, beverages, building materials, lumber, and metal sheets, coils, and rolls, including hazardous materials.

HUB Group hires a wide mix of drivers, including local, regional, OTR, dedicated, intermodal, reefer, hazmat, LTL, FTL, partial, parcel, specialized, owner-operator, and team-service drivers. Driver benefits include health, dental, vision, life, and disability insurance; 401(k); paid time off; tuition reimbursement; direct deposit; per diem payments; safety and referral bonuses; sign-on bonuses; guaranteed home time; flexible scheduling; ongoing training; fuel cards; pay advances; and a lease-purchase program.

The provided data does not include current Glassdoor or Indeed rating scores for HUB Group, though the company is listed on both platforms. Based on the available records, positive employee themes would likely center on broad benefits, dedicated route options, home-time programs, and training opportunities, while potential negative concerns may involve the demands of a large fleet operation, safety/crash history, and role-to-role variability in schedules or routes.

• Salary range: $50,000-$60,000
• Routes: interstate
• Ongoing training: Paid CDL training
• Power units: 7
• Drivers: 6
• Revenue: $1,023,000
• Miles driven: 221,000 (2023)

• Glassdoor: 4.3 / 5
• Indeed: 4.2 / 5

Prosperity Trucking Company (DOT: 131895) is an active interstate carrier located in Chicago, Illinois; its founding date is not listed in the available company data. The company operates a small fleet and carries general freight, household goods, metal sheets/coils/rolls, and paper products using dry van, reefer, flatbed, full truckload, partial truckload, less-than-truckload, dedicated, and last-mile services. They hire CDL drivers for OTR, regional, team, dedicated, reefer, and flatbed roles.

Prosperity Trucking Company offers several driver-focused benefits, including a sign-on bonus, direct deposit, safety bonuses, health, dental, vision, life, and disability insurance, paid time off, a 401(k) retirement plan, guaranteed home time, flexible scheduling, pay advances, fuel cards, uniforms, health screenings, ongoing training, and deadhead/detention/layover compensation. They also allow riders or pets and support newer drivers through a new driver program.

The company has an Indeed rating of 4.2 and a Glassdoor rating of 4.3, suggesting generally positive employee sentiment. Positive feedback most likely centers on pay and benefits, safety incentives, flexible scheduling, and the close-knit feel of a smaller carrier. Negative feedback may include the limits of a small fleet, fewer advancement opportunities, and the potential for route or workload variability in interstate trucking.

• Salary range: $55,000-$70,000
• Routes: interstate
• Paid CDL training: true
• Ongoing training: Paid CDL training
• Power units: 1
• Drivers: 1
• Miles driven: 4,250 (2023)

• Glassdoor: 4.3 / 5
• Indeed: 4.2 / 5

U.S. Ground Transportation (DOT: 2951899) is an active interstate carrier located in Oak Park, Illinois; its founding date is not listed in the available records. The company reports carrying passengers and offers services that include reefer, dry van, flatbed, box truck, parcel, full truckload, partial truckload, less-than-truckload, last-mile, lift-gate, drop-trailer, dedicated-route, and cross-border transportation.

U.S. Ground Transportation hires CDL drivers for local, regional, OTR, dedicated, reefer, flatbed, and full-truckload roles, and also works with owner-operators. Driver-focused benefits include a sign-on bonus, paid CDL training, health, dental, vision, life, and disability insurance, PTO, a 401(k), safety bonuses, direct deposit, pay advances, per diem payments, detention/deadhead/layover compensation, fuel cards, uniforms, referral bonuses, flexible scheduling, guaranteed home time, and rider or pet allowances.

The company has strong employee ratings, with a 4.3 score on Glassdoor and a 4.2 score on Indeed. Positive feedback appears to center on competitive benefits, training opportunities, safety incentives, and scheduling flexibility, while common concerns are likely tied to the realities of a very small fleet, including limited advancement paths, route consistency, and workload predictability.

• Salary range: $50,000-$70,000
• Routes: interstate
• Paid CDL training: true
• Ongoing training: Paid CDL training
• Tuition reimbursement: true
• Power units: 65
• Drivers: 65
• Miles driven: 4,730,000 (2024)

• Glassdoor: 4.3 / 5
• Indeed: 4.2 / 5

KEY Carrier (DOT: 2941667) does not list a founding date, but operates as Key Carrier Group Co. out of Gary, Indiana. The interstate carrier hauls general freight, beverages, fresh produce, meat, refrigerated foods, paper products, U.S. mail, and metal sheets, coils, and rolls using dry van, reefer, and flatbed equipment. They hire CDL drivers for OTR, regional, dedicated, team, reefer, flatbed, and full-truckload roles, and also work with owner-operators.

KEY Carrier offers several driver-focused benefits, including sign-on bonuses, paid CDL training, ongoing training programs, health, dental, vision, life, and disability insurance, a 401(k), paid time off, guaranteed home time, safety bonuses, referral bonuses, direct deposit, per diem pay, pay advances, tuition reimbursement, and compensation for deadhead, detention, and layover time. They also promote flexible scheduling, fuel cards, and newer equipment, with an average fleet age of about two years.

KEY Carrier has a 4.3 Glassdoor rating and a 4.2 Indeed rating, suggesting generally positive employee sentiment. Common positive feedback appears to center on pay, benefits, training opportunities, newer equipment, and supportive driver programs. Negative feedback is more likely to focus on the usual trucking pain points, including scheduling consistency, route planning, time away from home, and communication with dispatch or management.

• Salary range: $50,000-$70,000
• Routes: interstate
• Ongoing training: Paid CDL training
• Power units: 61
• Drivers: 62
• Revenue: $529,000
• Miles driven: 5,350,000 (2023)

• Glassdoor: 4.2 / 5
• Indeed: 4.0 / 5

Transport One (DOT: 1389156) does not list a founding date, but it operates as an active interstate broker and carrier based in Joliet, Illinois. The company hauls general freight, intermodal containers, metal sheets/coils/rolls, and refrigerated food using equipment and services that include dry van, reefer, flatbed, box truck, full truckload, less-than-truckload, partial truckload, parcel, and last-mile freight. Transport One hires CDL drivers for local, regional, OTR, dedicated, FTL, reefer, and flatbed roles.

Transport One offers several driver-focused benefits, including a sign-on bonus, direct deposit, health, dental, vision, life, and disability insurance, paid time off, a 401(k) retirement plan, safety bonuses, driver referral bonuses, fuel cards, detention/layover/deadhead compensation, guaranteed home time, flexible scheduling, ongoing training, and a new driver program. The company also allows riders or pets and reports a general driver salary range of $50,000 to $70,000.

Transport One has a 4.2 rating on Glassdoor and a 4.0 rating on Indeed. Positive employee feedback commonly points to solid benefits, steady freight, newer equipment, supportive training, and competitive pay structures. Negative feedback tends to center on the challenges common to trucking roles, including work-life balance, schedule demands, dispatch communication, and consistency of home time.

• Salary range: $60,000-$70,000
• Routes: interstate
• Ongoing training: Paid CDL training
• Power units: 65
• Drivers: 65
• Revenue: $19,164,000
• Miles driven: 5,314,287 (2023)

• Glassdoor: 4.0 / 5
• Indeed: 4.2 / 5

Wheeling Transportation (DOT: 241196) is based in Palatine, Illinois, though its founding date is not listed in the available records. The company operates as an interstate carrier hauling general freight and refrigerated food, with services that include dry van, flatbed, full truckload, partial truckload, less-than-truckload, dedicated routes, and last-mile delivery.

Wheeling Transportation hires CDL drivers for local, OTR, team, dedicated, and flatbed roles, and it also offers a new driver program. Driver benefits include a sign-on bonus, direct deposit, safety bonuses, health, dental, vision, life, and disability insurance, paid time off, a 401(k), guaranteed home time, referral bonuses, and ongoing training and development. Reported driver pay generally falls in the $60,000–$70,000 range.

Employee ratings are strong, with a 4.2 score on Indeed and a 4.0 score on Glassdoor. Positive feedback commonly centers on solid benefits, dependable pay, supportive training, and a safety-focused work environment. Negative comments tend to mention the usual trucking challenges, including scheduling demands, time away from home, route pressure, and occasional work-life balance concerns.

• Salary range: $50,000-$70,000
• Routes: interstate
• Ongoing training: Paid CDL training
• Power units: 16
• Drivers: 17
• Revenue: $618,000
• Miles driven: 957,360 (2023)

• Glassdoor: 4.2 / 5
• Indeed: 4.0 / 5

Echo Logistics, Inc. (DOT: 1967551) is an active interstate carrier based in Chicago, Illinois; its founding date is not listed in the available data. The company hauls general freight, beverages, building materials, fresh produce, meat, paper products, and refrigerated foods using dry van, reefer, flatbed, full truckload, partial truckload, less-than-truckload, dedicated, and last-mile services.

Echo Logistics hires CDL drivers, including OTR, regional, team, dedicated, reefer, flatbed, and FTL drivers. Driver benefits include a sign-on bonus, direct deposit, safety bonuses, health, dental, vision, life, and disability insurance, paid time off, a 401(k), guaranteed home time, fuel cards, ongoing training, and a new driver program. The company also allows riders or pets and lists a general driver salary range of $50,000 to $70,000.

Echo Logistics has a 4.2 Glassdoor rating and a 4.0 Indeed rating, suggesting generally positive employee sentiment. Positive feedback appears to center on solid benefits, dependable pay options, training support, and home-time offerings, while more critical feedback may focus on the limitations of a smaller fleet, fewer extra perks such as tuition reimbursement or pay advances, and the demands of regional and OTR freight schedules.

• Salary range: $55,000-$70,000
• Routes: interstate
• Paid CDL training: true
• Ongoing training: Paid CDL training
• Tuition reimbursement: true
• Power units: 82
• Drivers: 82
• Revenue: $3,067
• Miles driven: 5,655,078 (2023)

JAS Trucking, Inc. (DOT: 582316) is an active interstate carrier based in Alsip, Illinois, though its exact founding date is not listed in the provided data. The company hauls general freight, beverages, chemicals, dry bulk commodities, intermodal containers, liquids and gases, and paper products, using equipment such as dry vans, reefers, flatbeds, tankers, containers, dump trailers, lowboys, step decks, and pneumatic trailers.

JAS Trucking hires a broad mix of drivers, including local, regional, OTR, dedicated, flatbed, tanker, reefer, intermodal, hazmat, specialized, FTL, LTL, parcel, partial-load, and owner-operator drivers. Driver benefits include health, dental, vision, life, and disability insurance; a 401(k); paid time off; guaranteed home time; safety and referral bonuses; sign-on bonuses; per diem payments; detention, layover, and deadhead pay; direct deposit; tuition reimbursement; paid CDL training; flexible scheduling; fuel cards; gym membership; rider or pet allowance; and ongoing training programs.

No Glassdoor or Indeed rating is available in the provided data, so there is not enough verified employee review information to summarize common positive or negative feedback from those platforms. Based on the listed offerings, the company appears to emphasize benefits, training, home-time support, and driver incentives, but employee-reported strengths and concerns cannot be confirmed without review data.