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Top Chicago, IL Transportation Companies With Best Work-Life Balance (188)

Mastery Logistics Systems
Enterprise Web • Logistics • Software • Transportation
3 Offices
500 Employees
35 Benefits
Mastery is on a mission to empower shippers, carriers & logistics companies to thrive in complexity.

Mastery is the World’s First Lovable Transportation Management System™ (TMS) built to support the complex world of logistics and supply chain. Mastery brings to market MasterMind™, a cloud-based SaaS technology solution for large complex organizations, providing interconnected automation, visibility, and productivity across their supply chains.

Mastery Logistics Systems

Mastery Logistics Systems's Top Work-Life Balance & Wellbeing Strengths

Remote or Hybrid Flexibility: Company materials highlight remote and hybrid options, with roles posted as fully remote or flexible by schedule and location. Typical time on site is described as flexible.

Time Off Access: Employer information cites unlimited PTO and a company-wide winter break from Christmas Day through New Year’s Day. Some roles also encourage taking at least a week off periodically.

Boundary Respect: Stated norms include no‑meeting Fridays and guidance to limit after‑hours pings (e.g., avoid Slack after 7 p.m.). These practices are positioned to protect focus time and reduce evening interruptions.

Toro TMS
Cloud • Enterprise Web • Sales • Software • Transportation
Chicago
80 Employees
37 Benefits Hiring Now
Easy-to-use TMS built for Bulk Haulers

At Toro TMS, we are on a mission to deliver technology that drives lasting improvements for the trucking industry. Our dedicated team has built an easy-to-use, modern end-to-end TMS specifically designed for bulk haulers. From load management and dispatch, to accounting and driver payroll, we provide a single software solution to help our customers move more loads.

Toro TMS

Toro TMS's Top Work-Life Balance & Wellbeing Strengths

Time Off Access: Benefits listings highlight unlimited PTO, paid holidays and sick time, company‑wide vacation, and generous parental leave that make stepping away feasible. These policies are presented as supporting everyday wellbeing and recovery.

Remote or Hybrid Flexibility: Public profiles describe remote or hybrid options for some roles, including fully remote in certain engineering positions, enabling control over schedule and location. Defined in‑office expectations add clarity to how flexibility works in practice.

Supportive Culture: Content highlights collaborative, mission‑driven teams with approachable leadership that fosters a respectful, low‑ego environment. Regular 1:1s and visible recognition are described as reducing ambiguity and reinforcing support.

FourKites
Artificial Intelligence • Big Data • Logistics • Machine Learning • Software • Transportation
4 Offices
475 Employees
55 Benefits Hiring Now
Leading Supply Chain Technology

Our platform creates comprehensive digital twins of your supply chain with AI-powered digital workers to automate resolution, improve collaboration and drive outcomes across all stakeholders. Unlike traditional control towers, we enable true real-time execution and intelligent fulfillment, transforming both your supply and customer-facing operations.

FourKites

FourKites's Top Work-Life Balance & Wellbeing Strengths

Remote or Hybrid Flexibility: A hybrid setup with flexible start/end times and remote options in some roles enables employees to adjust where and when work gets done. Flexibility by team and site can help accommodate global collaboration demands.

Recovery Time: Generous PTO, company-wide recharge days, and paid parental leave provide structured opportunities to disconnect and recover during peak periods. Wellness initiatives and volunteer time further support stepping away when needed.

Supportive Culture: Approachable managers, supportive colleagues, and employee resource groups are emphasized as day-to-day supports that help keep balance workable when teams are run well. Culture committees and engagement efforts aim to strengthen connection across hybrid teams.

SRAM, LLC
Fitness • Hardware • Mobile • Software • Sports • Transportation • Esports
SRAM is a manufacturer of innovative bicycle components that was founded in Chicago, Illinois, in September of 1987.

Founded in Chicago in 1987 by Stan Day, SRAM, LLC has grown to be one of the world's largest bicycle component manufacturers. Today, we are led by CEO, Ken Lousberg, and Stan Day serves as Chairman of our Board. SRAM’s global footprint helps us bring cycling to every corner of the globe, including your local roads and trails. We design and...

SRAM, LLC

SRAM, LLC's Top Work-Life Balance & Wellbeing Strengths

Work-Life Reputation: Work-life balance is described as good to very good, underpinned by a relaxed, collaborative culture.

Time Off Access: Generous PTO that grows with tenure, paid holidays and sick time, and an annual year‑end shutdown make time away predictable.

Wellbeing Programs: Weekly lunch rides, in‑house yoga and run clubs, wellness reimbursements, and paid volunteer time encourage holistic wellbeing.

Edge Logistics
Logistics • Sales • Transportation
Chicago
120 Employees
26 Benefits
We deliver superior transportation management solutions to our customers through efficiency, technology and innovation.

Our Mission is Simple! Edge delivers superior transportation management solutions to our customers through efficiency, technology, and innovation. Edge has an unmatched history of data and analytics through its CAPACITY platform that utilizes proprietary algorithms to improve data research. Our employees understand the value and importance of leveraging these strengths in a competitive transportation market and promote a strong working...

Edge Logistics
Sleek Fleet
Logistics • Software • Transportation
Chicago
20 Employees
19 Benefits
Sleek Fleet is a web-based app that connects drivers and shippers together.

Now in its 3rd year, Sleek Fleet’s ongoing push to redefine digital freight brokerage has disrupted an outdated freight brokerage model and has advanced the shipper/driver relationship while increasing profitability for both sides. Sleek Fleet’s sleek web-based app has already helped thousands of drivers take back their pay and shippers cut cost.

Sleek Fleet
CANDOR EXPEDITE INC
Transportation
3 Offices
21 Employees
15 Benefits

Candor Expedite creates fast, effective, and sustainable solutions for time-sensitive shipments; powered by an experienced team and trustworthy carrier network.

CANDOR EXPEDITE INC
RB Global
Automotive • eCommerce • Transportation • Energy • Agriculture • Industrial
Westchester
445 Employees
Hiring Now

RB Global, Inc. (NYSE: RBA) (TSX: RBA) is a leading, omnichannel marketplace and trusted provider of value-added insights, services and transaction solutions for buyers and sellers of commercial assets and vehicles worldwide. Through its global network of auction sites and digital platform, RB Global serves customers worldwide across a variety of asset classes, including automotive, construction, commercial transportation, government surplus,...

RB Global

RB Global's Top Work-Life Balance & Wellbeing Strengths

Remote or Hybrid Flexibility: Remote options and hybrid setups are highlighted for many corporate/technology roles, which helps maintain balance when daily work is not tied to on‑site events. Schedule autonomy and WFH flexibility ease day‑to‑day demands in those teams.

Time Off Access: PTO, holidays, and the ability to take time away are emphasized, indicating accessible time‑off structures. These programs support recovery after peak periods.

Wellbeing Programs: Wellness resources such as EAPs, gym memberships, and tuition support are promoted as part of the employee offering. These benefits contribute to wellbeing alongside core benefits like retirement and healthcare.

FleetPulse
Artificial Intelligence • Logistics • Transportation
Chicago
19 Employees
Hiring Now

FleetPulse™ is the leading trailer telematics company that enables end-to-end visibility into trailer safety and cargo security, serving customers with OEM-agnostic wired and aftermarket telematics offerings. Based in Chicago, Illinois, FleetPulse combines deep roots in the trucking industry with expert tech talent and offers telematics solutions across a comprehensive portfolio of devices, from hard-wired, OEM-installed sensors to easy-to-install aftermarket sensors and...

FleetPulse
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The BusBank
Transportation • Travel
Chicago
22 Employees

The BusBank is a group and event transportation service. We are "The Easy Way to Charter a Bus - Anywhere in North America." We make it easy to get exactly the right bus, at the right price,  in the right place. We are a transportation and event service specializing in the bus charter  We also handle bus quality, logistics and seasonal...

The BusBank
newtrul
Logistics • Transportation
Chicago
12 Employees

Our mission is to empower Brokers + Carriers to stay competitive with better online freight booking, world-class automation, and real-time market data. We make it easy for Carrier reps to expand their reach, book directly online, and win more loads & lanes! Connect to newtrul and grow your business via digital bookings without spending a fortune on complex software integrations. Get Started...

newtrul
SP+ (SP Plus)
Events • Other • Security • Software • Transportation
25 Offices
10,001 Employees
25 Benefits

SP+ facilitates the efficient movement of people, vehicles and personal belongings with the goal of enhancing the consumer experience while improving bottom line results for our clients. The Company provides professional parking management, ground transportation, remote baggage check-in and handling, facility maintenance, security, event logistics, and other technology-driven mobility solutions to aviation, commercial, hospitality, healthcare and government clients across North...

SP+ (SP Plus)
Pace Suburban Bus
Social Impact • Transportation
8 Offices
5,000 Employees

Pace Suburban Bus is the premier suburban transit provider, safely and efficiently moving people to work, school, and other regional destinations. It offers affordable, innovative, and environmentally responsible public transportation services to residents in the Chicago metropolitan area.

Pace Suburban Bus
Imperative Logistics Group
Logistics • Transportation
2 Offices
53 Employees

Imperative Logistics Group is a diversified supply chain management company, offering a unique portfolio of complementary, premium logistics services. We specialize in Global Forwarding, U.S./Mexico Cross-Border Solutions, Mission Critical Domestic, Expedite Services, and Fine Arts..

Imperative Logistics Group
Optimas
Automotive • Transportation • Industrial • Manufacturing
28 Offices
1,162 Employees
32 Benefits

Optimas is a global supplier and manufacturer of C-class components, including fasteners, enclosures, cable management, and finishing products. They provide integrated supply chain solutions for the Industrial Machinery & Equipment, Manufacturing, and Automotive sectors.

Optimas
Freight Management, Inc
Glendale Heights
50 Employees

Freight Management, Inc is a Logistics Service Provider with over 30 years in the transportation industry that uses its proprietary TMS technology, My Freight Manager, to manage our customers' transportation.

Freight Management, Inc
R+L Global Logistics
Logistics • Transportation
13 Offices
522 Employees
14 Benefits

We empower businesses worldwide to ship smarter. R+L Global Logistics strives to provide the best freight solutions and logistics services to our customers. We offer the highest quality domestic and international transportation services including Full Truckload (FTL), Intermodal/Rail, Expedited/Domestic Priority, Service to and from Mexico and Canada, Trade Show, Supply Chain Management, High Value/High Risk Cargo, Warehousing and Fulfillment, Value Added,...

R+L Global Logistics
MVMNT
Fintech • Logistics • Payments • Software • Transportation
Chicago
20 Employees
16 Benefits
When you work at MVMNT, you’re tackling real life problems—and shaking up a trillion dollar industry in the process.

Transform a Trillion Dollar Industry When you work at MVMNT, you’re tackling real life problems—and shaking up a trillion dollar industry in the process. MVMNT is a Chicago-based freight tech startup founded in 2020. Our mission is to enable small & medium-sized brokerages with enterprise-level technology and embedded financial services to give them a leg up on the big guys. One...

MVMNT
Digital Fleet
Hardware • Software • Transportation
Fully Remote
27 Employees
9 Benefits

We build telematics software and hardware that is used by the construction industry to optimize the delivery of products. We are a small team that believes in autonomy, transparency, and that rapid, continuous improvement (not just to our product, but to everything we do) is the best way to ensure that we are always delivering the best value to our...

Digital Fleet
XPO
Transportation • 3PL: Third Party Logistics
33 Offices
38,000 Employees
26 Benefits

XPO is the transportation industry’s original disruptor. We’ve been investing in transportation automation and digitization for more than a decade, innovating how goods move through supply chains. Our tech-connected network of terminals and fleet is built to deliver freight with greater visibility, faster and more efficiently. Our technology provides real-time visibility into shipment status, streamlines tasks through automation and offers...

XPO

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