Our Mission

We are a global chauffeured transportation company honoring our commitments and exceeding customer expectations by employing and investing in the most passionate, loyal and dedicated professional team.

Why Windy City Limousine?

The chauffeured transportation industry is unlike any other industry you have worked for before. There is a general sense of family and wanting to learn from one another and seeing each other succeed. Windy City Limousine is highly regarded as one of the best in the industry. Why? Because we were one of the fastest growing companies in the US. Our leadership gives back to the industry by sitting on committees and mentoring smaller operators. Our customer service is top notch. Our team members drive the success of the company and we encourage a culture of ownership mentality bound by trust, respect, and loyalty.

Benefits + Perks

Employee Discounts

Employee Discounts

  • Employees receive a 20% discount on any transportation they take and a 10% discount to extend to friends and family.
  • Vehicle maintenance discounts in our onsite shop (oil changes, fluid top offs, windshield wipers)
Plan for the Future

Plan for the Future

  • 401(k) retirement plan with company match
  • Life insurance plans
  • Flexible spending accounts
Staying Healthy

Staying Healthy

  • Medical, dental and vision insurance plans
  • Gym membership reimbursement options
  • Real Appeal (digital weight loss program) included with medical insurance
  • Critical Illness and Accident Insurance
Time Off

Enjoying Time Off

  • Paid holidays to celebrate: New Year’s Day, Memorial Day, Independence Day, Labor Day, Thanksgiving Day, Christmas Day
  • Paid vacation days to recharge: 1-5 years of employment: 10 days per year; 6-10 years of employment: 15 days per year; Over 10 years of employment: 20 days per year
Further Education

Further Education

  • Windy City regularly offers employees opportunities to partake in webinars or seminars that will help them grow in their career path
  • Education Reimbursement to employees wishing to continue their education to secure increased responsibility and growth within their professional careers

Work Hard, Play Hard

  • Annual BBQs
  • Company gatherings/outings throughout the year
  • Regular raffles for tickets to sporting and theater events

Community Involvement

  • Participate in Make a Wish Walk for Wishes
  • Annual collection/donation to Ronald McDonald House
  • Toys for Tots
  • Giving back to our community by donating vehicles for various events


We LOVE our team!

  • Annual Employee Recognition Awards Ceremony
  • Monthly “props” amongst colleagues to recognize those going “Above and Beyond”