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
• 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) is a reputable trucking company known for its robust service offerings and dedication to its drivers. Although the exact founding date is not specified, KEY Carrier has established itself as a reliable player in the industry, operating predominantly in interstate trucking. The company primarily carries a variety of cargo, including beverages, fresh produce, general freight, meat, metal sheets, coils, rolls, paper products, refrigerated foods, and US mail. The company hires both team and dedicated drivers, with opportunities for flatbed, OTR, and reefer drivers, enhancing its versatility and scope of operations.

KEY Carrier is applauded for its competitive driver benefits, including sign-on bonuses, paid CDL training, and tuition reimbursement to support driver education. The benefits package also includes comprehensive health insurance with dental and vision coverage, life insurance, a retirement plan, and PTO. For added financial security, they offer deadhead, detention, and layover compensation, alongside per diem payments. However, passenger allowance is not currently offered. Despite the absence of a truck lease purchase program, drivers appreciate the flexible scheduling and guaranteed home time, which contribute positively to work-life balance.

On review platforms such as Glassdoor and Indeed, KEY Carrier boasts strong ratings of 4.3 and 4.2, respectively. Employees consistently praise the company for its attentive approach to compensation and benefits, as well as the culture of safety encouraged through safety bonuses and ongoing training programs. However, some employees have pointed out areas for improvement, such as the availability of company uniforms and on-the-road amenities, nor does it offer special lounges or rest stops. Overall, feedback indicates a positive perception of job security and career advancement opportunities, despite minor organizational shortcomings.

• 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) has a long-standing presence since its inception, offering substantial industry experience. The company is headquartered in an undisclosed location but operates in the interstate trucking landscape. HUB Group specializes in transporting a variety of cargo including beverages, building materials, general freight, intermodal containers, logs, poles, beams, lumber, metal sheets, coils, and rolls, as well as refrigerated food. They predominantly hire regional, local, OTR, intermodal, reefer, and specialized drivers.

HUB Group provides a range of enticing driver benefits including safety bonuses, guaranteed home time, and deadhead detention layover compensation. They offer flexible scheduling, per diem payments, and pay advances along with health, dental, vision, and life insurance benefits. Their impressive package includes tuition reimbursement and a supportive employee stock ownership program. Notably, HUB Group attracts drivers through a strong recruitment incentive of sign-on bonuses and a 401k retirement plan.

While specific employee ratings on Glassdoor and Indeed are not provided, anecdotal feedback from employee reviews often highlights the company's comprehensive compensation packages and robust benefits as major positives. However, some negative feedback addresses work-life balance, indicating potential challenges in consistently delivering home time. Overall, HUB Group is well-regarded for its compensation, employee benefits, and commitment to driver satisfaction.

• 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) is a trucking company operational since its establishment over 18,000 days ago. While the exact founding year is not specified, the company is actively engaged in the transportation industry from their base in an unspecified city and state. They specialize in carrying a variety of cargo types including chemicals, general freight, intermodal containers, and paper products. Keller Trucking hires a diverse range of drivers, including those for dry van, flatbed, and reefer operations, with opportunities available for regional, local, OTR, and dedicated routes.

Keller Trucking Co, Inc. offers several appealing benefits to its drivers, such as a sign-on bonus and direct deposit. The company provides health, dental, and vision insurance while also offering a retirement plan (401k), paid CDL training, and ongoing training and development programs. Additional perks include paid time off, safety bonuses, and deadhead and detention layover compensation. They also offer a driver referral bonus, a commitment to guaranteed home time, and the flexibility for team driving, making the company an attractive employer in the trucking sector.

The company has received positive feedback on both Indeed and Glassdoor, boasting scores of 4.1 and 3.8, respectively. Employees appreciate the competitive compensation, benefits, and work culture. However, there are occasional concerns regarding work-life balance and route management. Despite these issues, Keller Trucking maintains a satisfactory safety rating and a strong reputation for reliability and employee satisfaction in the transportation industry.

• 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) operates under the legal name Odyssey Specialized Logistics LLC. The company is active in the logistics and transportation industry, providing services since its establishment, though the specific founding year is not mentioned. Based in the United States, Area Transportation offers a comprehensive array of services centered on general freight. They handle various types of cargo including beverages, building materials, construction equipment, general freight, grain, feed, hay, intermodal containers, logs, poles, beams, lumber, machinery large objects, metal sheets, coils, rolls, paper products, and utilities. The company employs regional, local, OTR, and specialized drivers, primarily hiring for roles that involve running interstate operations. They seem to cater to both individual and team drivers, as team driver opportunities and service are noted.

Area Transportation provides several benefits to its drivers, enhancing their employment experience. Notable benefits include a sign-on bonus, participation in a 401(k) retirement plan, direct deposit, and guaranteed home time. Health, dental, and vision insurance are available, as well as paid time off. Additionally, the company offers safety bonuses, ongoing training and development programs, and roadside assistance programs. Drivers also benefit from deadhead, detention, and layover compensation, reflecting the company’s commitment to compensating time effectively. However, pet and passenger allowances are not part of their offerings, nor is there tuition reimbursement.

Employee feedback reveals a mixed reception, with an Indeed rating of 4.5 indicating a generally positive experience, while a Glassdoor rating of 2.8 suggests room for improvement. Employees generally appreciate the compensation, benefits, and guaranteed home time, emphasizing these as positive aspects. However, negative reviews often highlight concerns about work-life balance and occasional disorganization in routing assignments. Frequent positive feedback celebrates the competitive pay and supportive work culture, whereas negative comments occasionally mention dissatisfaction with the lack of pet policy and stricter scheduling flexibility.

• 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 a reputable carrier known for its diverse transportation offerings. Despite some missing details about the exact founding year, this company continues to stand strong in the industry, headquartered in a location that remains unspecified. U.S. Ground Transportation specializes in transporting a variety of freight types, including refrigerated cargo and partial and full truckloads. They utilize a fleet that includes dry vans and flatbeds, catering to local, regional, and over-the-road transport needs. The company is known for employing both flatbed drivers and drivers for reefers, ensuring a wide range of shipment capabilities.

The company provides an array of benefits designed to attract and retain skilled drivers. Among these are competitive driver salaries ranging from $55,000 to $70,000, sign-on bonuses, and guaranteed home time, affirming their commitment to work-life balance. U.S. Ground Transportation offers comprehensive health benefits, including medical, dental, and vision coverage, along with a 401(k) retirement plan, paid time off, and life and disability insurance. Additionally, they provide opportunities for flexible scheduling, ongoing training, and development programs, supporting drivers in their professional growth. They also allow for riders and pets, which is appreciated by many driving professionals.

U.S. Ground Transportation has garnered positive feedback on both Indeed and Glassdoor, boasting ratings of 4.2 and 4.3 respectively. Employees frequently commend the company for its beneficial compensation packages, robust benefits, and strong job security. However, some employees express challenges with certain operational aspects, such as the efficiency of route scheduling. Nonetheless, U.S. Ground Transportation maintains a positive workplace culture, underscored by an emphasis on worker safety and satisfaction.

• 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) is a distinguished trucking company based in Chicago, Illinois. Although the exact founding date is not provided, Transport One is actively engaged in the trucking industry, primarily specializing in the transportation of various kinds of freight. They carry general freight, refrigerated foods, metal sheets, coils, and rolls, as well as intermodal containers. The company operates dry van and flatbed trucks, catering to a wide range of cargo transportation needs. Transport One hires a variety of drivers, including regional, dedicated, flatbed, and over-the-road (OTR) drivers, ensuring comprehensive service across different sectors of the logistics industry.

Transport One offers an array of benefits aimed at attracting and retaining top-notch drivers. These include health insurance plans covering medical, dental, and vision, alongside life insurance and disability coverage. They provide paid time off, 401(k) retirement plans, safety bonuses, and guaranteed home time. Transport One also focuses on continuous driver development through ongoing training programs. For those new to the industry, they have a new driver program to help budding drivers transition smoothly into their roles. The company is noted for offering competitive salaries ranging from $50,000 to $70,000, along with flexible scheduling to maintain a healthy work-life balance for their drivers.

On employee review platforms like Indeed, Transport One scores a respectable 4.0 out of 5, while Glassdoor data suggests an even higher rating of 4.2. Employees commonly praise the company for compensation, benefits, and a supportive work environment. The most positive feedback highlights the robust benefits package, supportive management, and reliability in delivering on their commitments for home time. However, some negative feedback points to occasional inconsistencies with route assignments and operational disorganization. Despite these occasional criticisms, Transport One maintains a strong reputation in the trucking industry, fostering a positive work culture that is evident in driver satisfaction scores.

• 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 a well-recognized trucking firm that has been active since its establishment, as indicated by its DOT age of over 18,000 days. The company is situated in the trucking industry hub and operates as an interstate carrier. Prosperity Trucking is proficient in transporting various types of cargo, including general freight, household goods, metal (sheets, coils, rolls), and paper products. They maintain a versatile fleet that includes dry van and flatbed trucks, catering to a range of cargo needs. The company primarily hires regional, dedicated, solo, and team drivers, offering opportunities for both flatbed and reefer drivers.

Prosperity Trucking Company offers several competitive benefits to attract and retain drivers. They provide health insurance, which includes dental and vision coverage, life and disability insurance, and a retirement 401(k) plan. Drivers also benefit from paid time off, guaranteed home time, and safety bonuses. The company values driver satisfaction, as evidenced by their flexible scheduling, ongoing training and development programs, and deadhead detention and layover compensation. Additionally, Prosperity Trucking supports drivers through direct deposit, pay advances, and rider or pet policies.

The company has garnered positive reviews from employees on Glassdoor, with a rating of 4.3. Employees appreciate the competitive compensation, benefits, job security, and the company's positive work culture. However, some feedback suggests occasional challenges with work-life balance, where home time and route organization can sometimes be less than ideal. Prosperity Trucking continues to work on improving these areas to enhance overall employee experience and satisfaction.

• Salary range: $60,000-$70,000
• Routes: interstate
• Ongoing training: Paid CDL training
• Power units: 34
• Drivers: 34
• Revenue: $512,000
• Miles driven: 3,189,668 (2024)

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

M.S. Us, Inc. (DOT: 2335821) is a well-established trucking company that started operations over a decade ago. Based on their registration, they have been actively refining their services for 4381 days. The company specializes in transporting a wide array of cargo, including chemicals, fresh produce, general freight, meat, paper products, refrigerated foods, and U.S. mail. M.S. Us, Inc. employs various driver types, prominently featuring team drivers, reefer drivers, flatbed drivers, dedicated route drivers, and over-the-road (OTR) drivers.

Drivers at M.S. Us, Inc. benefit from several competitive advantages, including a sign-on bonus, guaranteed home time, and safety bonuses. They offer comprehensive health benefits such as medical, dental, vision, life, and disability insurance. Additional benefits include paid time off (PTO), a retirement plan (401k), and deadhead detention layover compensation. While they do not provide paid CDL training, ongoing training and development programs are available for their employees.

M.S. Us, Inc. garners favorable reviews on job platforms, with an Indeed rating of 4.2 and a Glassdoor rating of 4.0. Employees most often praise the company's compensation packages, benefits, and supportive work environment. However, some feedback highlights the company's areas for improvement, such as occasional challenges in maintaining work-life balance. Despite these concerns, the overall sentiment reflects a positive outlook on M.S. Us, Inc. as an employer in the trucking industry.

• 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) operates out of the state, although the precise founding date is not specified in their reports. They specialize in interstate transportation, utilizing a fleet of dry vans and flatbeds to carry general freight and refrigerated foods. Wheeling Transportation employs a variety of drivers, with a focus on team drivers, local, and over-the-road drivers. They also offer dedicated routes, providing reliability and consistency to their clients.

The company extends competitive benefits for its drivers, including a sign-on bonus, safety bonuses, health insurance (covering dental, vision, and life), paid time off, and a 401k retirement plan. Although they do not offer paid CDL training or a truck lease purchase program, their emphasis on ongoing training and development programs signals a commitment to advancing driver skills. Direct deposit payment provides convenience and security, although other perks like gym memberships and passenger or pet policies are not available.

Wheeling Transportation has favorable ratings on job sites, scoring 4.2 on Indeed and 4.0 on Glassdoor. Positive reviews frequently mention the competitive pay and comprehensive benefits package. Employees appreciate the guaranteed home time and structured route assignments. However, feedback can sometimes highlight issues with work-life balance and suggest improvements in scheduling flexibility. These insights paint a picture of a company focused on growth and development, with room for improvement in driver satisfaction regarding personal time.

• 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 a logistics carrier offering comprehensive freight services, though it does not specify a founding date or location in its records. The company operates interstate and handles a diverse range of cargo, including beverages, building materials, fresh produce, general freight, meat, paper products, and refrigerated foods. Echo Logistics primarily hires drivers for various roles including team, regional, dedicated, and OTR driving, utilizing flatbed, dry van, and reefer equipment.

Echo Logistics stands out with several attractive driver benefits, including a competitive salary range of $50,000 to $70,000, and perks like health, dental, and vision insurance, as well as a retirement plan (401k). Drivers also enjoy paid time off, life insurance, and the advantage of guaranteed home time, underscoring the company's commitment to employee satisfaction. The company additionally supports rookies with new driver programs and appreciates safety, offering bonuses for safe driving.

The company has a commendable Indeed rating of 4.0 and a Glassdoor rating of 4.2, reflecting its positive workplace environment. Employees often highlight the strong compensation and benefits, as well as the supportive organizational culture, while the company aims to improve in flexibility and organizational structure for scheduling. Most feedback indicates contentment with the professional growth opportunities provided by Echo Logistics.