Chauffeur Service in Winnetka, Wilmette & Kenilworth

Why Us?

Legacy Executive Limousine offers a premium black car service to the North Shore, encompassing Winnetka, Wilmette, and Kenilworth. From the stately residences along Sheridan Road to the delightful shops of Hubbard Woods, we provide a service standard that meets the high expectations of Chicago’s most discerning residents.

We are not a rideshare app; we are a dedicated private chauffeur service focused on safety, privacy, and dependability. Whether you need a secure ride to O’Hare, transportation for a student attending New Trier, or an unforgettable evening in the city, our chauffeurs are rigorously screened professionals committed to maintaining your confidentiality.

Airport Transfers (ORD, MDW & PWK)

For North Shore residents, timeliness is non-negotiable. We ensure your travel is seamless, whether you are flying commercial or private.

• O'Hare (ORD) Connections: The commute from Winnetka to O'Hare typically takes 30 to 45 minutes. We monitor traffic on the Edens Expressway (I-94) and Touhy Avenue to avoid bottlenecks. For 6:00 AM flights, our chauffeurs arrive 15 minutes early to help with luggage, ensuring you leave your home relaxed.

• Chicago Executive (PWK): We are the preferred service for private aviation flights out of Palwaukee. Our chauffeurs have tarmac access experience and provide discreet transfers for high-profile clients.

• Midway (MDW): While further away, we provide direct, comfortable transport to Midway via I-94, allowing you to work or rest during the longer drive.

Corporate & Executive Travel

We support the captains of industry who call the North Shore home.

• Downtown Commute: Skip the Metra Union Pacific North line. Our sedans serve as a private mobile office, allowing you to take conference calls in total privacy on your way to the Loop.

• Corporate HQs: We provide direct black car service to the corporate corridors in Northbrook, Deerfield, and Lake Forest.

• Guest Transport: Hosting clients or board members? We provide white-glove meet-and-greet services, transporting your guests from the airport to the Deer Path Inn or local country clubs.

Dining & Leisure

Enjoy the lifestyle of the North Shore without the hassle of parking.

• Local Dining: Enjoy a door-to-door evening at Sophia Steak in Wilmette, Pomeroy in Winnetka, or The Mino’s. We will wait for you or return for pickup the moment you are ready.

• Ravinia Festival: We provide drop-off service right at the gate for concerts at Ravinia, ensuring you skip the crowded parking lots and shuttle buses.

• Country Clubs: We offer spacious SUVs for golf outings to Indian Hill, Skokie Country Club, or Michigan Shores, with plenty of room for clubs.