Chauffeur Service in Winnetka & Limousine Rentals on the North Shore

Legacy Executive Limousine provides an exclusive, white-glove black car service to Winnetka, IL, and the nearby North Shore communities. From the historic estates along Sheridan Road to the charming boutiques of Hubbard Woods, we deliver a level of service that aligns with the expectations of Chicago’s most sophisticated residents.

We are not a rideshare app; we are a private chauffeur service committed to safety, privacy, and reliability. Whether you require a secure ride to O’Hare, transportation for a student at New Trier, or a memorable evening in the city, our chauffeurs are thoroughly vetted professionals who uphold your confidentiality.

Private Aviation & Airport Transfers

For residents of Winnetka, traveling with ease and comfort is a top priority. We excel in providing seamless connections between the beautiful North Shore and all major private and commercial aviation hubs, ensuring a smooth journey every time. 

• Chicago Executive Airport (PWK): Located just minutes away from PWK, we offer convenient tarmac-side pickups (where permitted) at trusted locations such as Signature Flight Support, Atlantic Aviation, and Hawthorne Global. Our service guarantees that your transition from air to ground is as effortless as possible, allowing you to focus on more important matters. 

• O’Hare International (ORD): The typical journey from Winnetka to O’Hare International Airport typically spans between 25 to 35 minutes, depending on traffic conditions. We utilize advanced flight tracking systems to closely monitor your flight's status, ensuring that your chauffeur is always ready to greet you at the curbside or baggage claim right as you arrive. With our commitment to punctuality and exceptional service, you can travel with confidence and stress-free style.

North Shore Lifestyle & Dining

Indulge in a delightful evening out without the usual stresses of finding parking or dealing with valet services. We take pride in offering seamless door-to-door transportation for your dinner reservations and social gatherings, ensuring that you can focus on enjoying your night to the fullest. 

• Fine Dining: Enjoy reliable and comfortable transport to renowned establishments such as Pomeroy, Aboyer, Mino's, or Sophia Steak. Your personal chauffeur will be conveniently on standby nearby, ready to collect you as soon as you've finished your meal, allowing for a smooth transition back home or to your next destination. 

• Country Clubs: Experience expert service as you head to prestigious locations like the Indian Hill Club and Skokie Country Club, whether for exciting golfing events or exclusive social gatherings. We'll make sure you're transported in style and comfort, enhancing your overall experience at these remarkable venues. 

• Ravinia Festival: Skip the hassle of congested trains and jam-packed parking lots. We provide direct drop-offs at the West Gate, ensuring you have a stress-free arrival for an unforgettable concert experience. Enjoy the music without worrying about how you'll get there or back.

A Fleet Designed for Comfort

Unlike rideshare vehicles, our fleet is owned, inspected, and detailed daily. 

• Cadillac Escalade ESV: The ultimate SUV for executives and families. Features seating for up to 6 passengers, privacy tint, and ample luggage space. 

• Lincoln Aviator & Volvo S90: Sleek, understated luxury sedans perfect for airport runs. 

• Mercedes-Benz Sprinter Vans: The ideal solution for corporate groups, bridal parties, or golf outings to the Country Club.