For the residents of Winnetka, transportation is about more than destination — it is about discretion and comfort. Experience the premier private car service trusted by the North Shore's most distinguished estates.
Private Aviation
PWK & O'Hare
Estate Care
Door-Through-Door
Club Events
Discreet Shuttles
A decade of serving the specific needs of the North Shore community.
The preferred private fleet for Winnetka and Glencoe residents. Trusted by your neighbors.
A decade of serving the specific needs of the North Shore community. Every detail refined.
Chauffeurs trained in strict privacy protocols and executive discretion. Complete confidentiality.
We elevate the airport transfer to a concierge level. Whether flying private out of PWK or commercial out of O'Hare, our service ensures every detail is managed with precision.
We handle the heavy lifting — from your foyer to the aircraft or terminal curb, and from baggage claim back to your residence. Your chauffeur manages every piece with care.
FAA-integrated monitoring for commercial arrivals. For private aviation, we coordinate directly with your FBO to ensure seamless timing as you taxi to the ramp.
Heading to Florida or Arizona for the season? Our SUVs are sized to handle trunks, golf clubs, and pet carriers with ease, ensuring a smooth start to your winter retreat.
Tarmac access for private aviation. FBO coordination and discreet aircraft-side pickup.
Premium terminal service with flight tracking and 45-minute complimentary wait.
Oversized luggage, golf clubs, pet carriers accommodated
For our senior clients, we provide a level of care that goes beyond the curb. Your chauffeur meets you at the front door, assists with coats and stability, and ensures you are settled comfortably.
We operate on your timeline. Our chauffeurs are patient, respectful, and trained to assist — never to rush. We provide peace of mind for travel to medical appointments or family visits.
Northwestern, Rush, Evanston Hospital — we wait and return you safely home.
Holiday gatherings, grandchildren's events, assisted living — dignified transport with care.
Walkers, canes, foldable wheelchairs — our SUVs accommodate mobility aids with discretion.
Enjoy a dinner at Sophia Steak or a show in the city without the logistics. With our "Wait & Return" service, your vehicle remains yours for the evening.
Eliminate the wait for valet or the walk to a parking garage. Your chauffeur coordinates via text for instant curbside pickup. Leave your belongings in the car and enjoy the night — we are waiting at the door when you are ready.
Hubbard Woods fine dining. No parking search, no valet queue.
Explore the North Shore's finest establishments. Wait & Return keeps your chauffeur on standby.
Gibson's, Maple & Ash, Chicago Athletic Association. Seamless city evenings.
Performance nights made effortless. Pickup at curtain, door-to-door.
Attending a gala or wedding at Indian Hill Club or Skokie Country Club? We specialize in discreet guest shuttles. Our Sprinter Vans move your party in luxury, ensuring everyone arrives safely and together.
Up to 14 passengers in our Executive Sprinter. High-roof comfort for formal attire, easy boarding for all guests.
Coordinated timing with your event schedule. Guests never wait — we run on club time, not ours.
Vehicles detailed daily and strictly smoke-free, matching the dress code and elegance of your event.
Perfect for: Wedding guest shuttles • Galas and charity events • Member functions • Anniversary celebrations • Rehearsal dinners • Corporate receptions
Winnetka's premier North Shore location provides excellent access to private aviation, O'Hare, and downtown Chicago.
| Destination | Distance | Off-Peak | Rush Hour | Route Notes |
|---|---|---|---|---|
| Chicago Executive (PWK) ✈️ | 8 miles | 12 – 18 mins | 18 – 28 mins | Private Aviation / FBO Access |
| O'Hare International (ORD) ⭐ | 16 miles | 22 – 30 mins | 35 – 50 mins | I-94 → I-190 direct |
| Chicago Loop / Downtown | 18 miles | 25 – 35 mins | 40 – 60 mins | Sheridan / Lake Shore Dr |
| Indian Hill Club | 1 mile | 3 – 5 mins | 5 – 8 mins | Local |
| Hubbard Woods / Sophia Steak | Local | 2 – 4 mins | 3 – 6 mins | Green Bay Rd |
✈️ Chicago Executive Airport (PWK) is just 8 miles from Winnetka — under 20 minutes for private aviation transfers.
Curated for the North Shore. Daily detailed, smoke-free, and presented to the standard your occasions demand.
"We've used Deluxe for years — the winter trips to Naples, the children's weddings, everything. The discretion is appreciated. The drivers are professional and, frankly, they remember our preferences. That matters to us."
— A Winnetka Family
Sheridan Road • Estate Clients
"The Door-Through-Door service for my mother's medical appointments has been exceptional. Patient, respectful, never rushed. The chauffeur knows her name and treats her with genuine kindness. It's given our family tremendous peace of mind."
— Jennifer C.
Winnetka • Assisted Mobility Client
Yes — privacy is a standard part of our service agreement. All chauffeurs are trained in strict confidentiality protocols and executive discretion. What happens in the car stays in the car. For clients who require additional privacy documentation, custom NDAs can be arranged.
Yes — we provide safe, tracked transport for students to events, proms, airports, and college visits. Parents receive confirmation and can track the vehicle. Our chauffeurs are background-checked and experienced with student transportation protocols.
Yes — we have extensive experience with FBOs at Chicago Executive Airport (PWK). We coordinate directly with your aviation team for seamless timing, meet you aircraft-side on the ramp, and ensure discreet, efficient transfers. We also service private terminals at O'Hare.
Winnetka to O'Hare rates start at $75 for an executive sedan and $95 for a luxury SUV. All rates are fixed at booking — no surge pricing. Tolls, flight tracking, and 45-minute arrival wait time included. Private aviation transfers to PWK are quoted individually.
Absolutely — Indian Hill Club, Skokie Country Club, and North Shore Country Club events are a specialty. We provide discreet guest shuttles, coordinate with event planners, and ensure vehicles are presented to the standard your occasion demands. Detailed daily, smoke-free, and matched to the elegance of the venue.
Winnetka is at the heart of Chicago's most distinguished communities. We proudly serve these neighboring estates with the same commitment to excellence.
From private aviation to Door-Through-Door estate care, Hubbard Woods dining to country club galas — experience the discretion and comfort the North Shore demands.
Private Aviation • Estate Care • Hubbard Woods Dining • Country Club Transport
Optimized by Seraphinite Accelerator