Daily rentals
Choose a luxury or exotic car and ask about delivery for your dates.
Chicago
Luxury & exotic car rentals in Winnetka, IL
DDE Rentals brings luxury and exotic car rentals to Winnetka, IL — Rolls-Royce, Lamborghini, Bentley, and the Mercedes G-Wagon delivered to your estate, hotel, or venue on the North Shore. Self-drive and chauffeured options are both available, with every car brought to your door and collected when the rental ends.
The DDE Rentals fleet
A different kind of drive.
Services for Winnetka
Find the right service.
Chauffeur service
Plan a chauffeured ride around your itinerary and occasion.
Cars for sale
Explore cars for sale or ask our team to help find your next car.
Daily rental rates are for self-drive bookings. Chauffeur service is quoted separately, with vehicle availability and delivery arrangements confirmed by our team.
For the occasion. For your day.
Prom arrivals
Plan a chauffeured prom arrival with your group and pickup details.
Wedding transport
Talk through wedding-day transport, timings and photo stops.
Private drivers
Ask about a private driver for an itinerary with multiple stops.
Vehicle transport
Request a vehicle transport quote for your pickup and destination.
Rental consignment
Explore earning rental income from your luxury or exotic car. Share the vehicle and where it is based so our team can discuss eligibility and next steps.
Find your car
Cars we deliver to Winnetka
A selection from the Chicago area fleet. Explore self-drive rates and security deposits, then check your dates and delivery plans.
Porsche 911 GT3 RS
4.0L naturally aspirated flat-six
Daily rental · from
$2,800/day
$7,500 security deposit
Rolls-Royce Cullinan
6.75L twin-turbo V12
Daily rental · from
$1,899/day
$2,500 security deposit
Lamborghini Urus (Blu)
4.0L twin-turbo V8
Daily rental · from
$1,699/day
$2,500 security deposit
Bentley Mulsanne
6.75L twin-turbo V8
Daily rental · from
$1,199/day
$3,500 security deposit
Audi R8 V10 Plus
5.2L V10
Daily rental · from
$1,199/day
$2,500 security deposit
Mercedes-Benz G63 AMG (G-Wagon)
2024
Handcrafted 4.0L biturbo V8
Daily rental · from
$1,000/day
$2,000 security deposit
Local knowledge
Make the most of Winnetka
Roughly sixteen miles up the North Shore along Green Bay Road and Sheridan Road, Winnetka is one of the wealthiest communities in Illinois — a village of estate homes, distinguished residential architecture, and three Metra stops on the UP-North line at Hubbard Woods, Winnetka, and Indian Hill. It is a place people already know from the screen — the Home Alone house on Lincoln Avenue and the National Historic Landmark Crow Island School sit among streets that turn up regularly as film and TV backdrops. That mix of quiet wealth and photogenic architecture is exactly why the cars come here — for North Shore weddings, milestone celebrations, and shoots that need a machine worthy of the setting. DDE delivers across Chicagoland to Winnetka and the neighboring ultra-affluent villages of Kenilworth and Glencoe, walking you through the car at handover and collecting it when you are done.
Weddings on the North Shore
A chauffeured Rolls-Royce for the ceremony and a self-drive exotic for the send-off — our team plans the timing around your day, from portraits to the last dance, at estates and venues across Winnetka and the North Shore.
Architecture & film-set shoots
Winnetka's estate homes and landmark streetscapes have long drawn producers and photographers — we position the right car for editorial shoots, content days, and productions where the backdrop and the machine have to match.
Ultra-luxury marques
Rolls-Royce Ghost and Cullinan, Bentley, and the Mercedes G-Wagon carry the presence a North Shore occasion asks for, alongside Lamborghini and Porsche — each listed with its daily rate and deposit up front.
Serving Kenilworth & Glencoe
Delivery reaches beyond Winnetka to adjacent Kenilworth — the wealthiest town in Illinois — and Glencoe, brought to the estate, hotel, or venue wherever the celebration is happening.
Delivered to your door
No counters and no shuttle buses — the car arrives at your home, hotel, or venue anywhere in Winnetka, timed around your plans, with pickup arranged when the rental ends.
Reserve online
Rates and deposits are published on every car. Verify your ID and insurance, then book and pay securely through GoLux — the keys arrive with the vehicle.
Explore areas we serve
View every service areaDDE delivers throughout the Chicago area. Explore our other serviceable areas:
- Chicago, IL
- Naperville, IL
- Hinsdale, IL
- Wheaton, IL
- Bolingbrook, IL
- O'Hare Airport
- Midway Airport
- Downers Grove, IL
- Rosemont, IL
- South Barrington, IL
- St. Charles, IL
- Oak Brook, IL
- Northbrook, IL
- Wilmette, IL
- Lake Forest, IL
- Glenview, IL
- Evanston, IL
- Highland Park, IL
- Elmhurst, IL
- Schaumburg, IL
- Burr Ridge, IL
- Orland Park, IL
- Bridgeview, IL
- Glen Ellyn, IL
- Carol Stream, IL
- Winfield, IL
- Romeoville, IL
- Woodridge, IL
- Deerfield, IL
- Kenilworth, IL
- Glencoe, IL
- Geneva, IL
- Batavia, IL
- Oak Lawn, IL
- Lombard, IL
- Lisle, IL
- Darien, IL
- Park Ridge, IL
- Palos Heights, IL
- Palos Park, IL
- Tinley Park, IL
- Lemont, IL
- Homer Glen, IL
- Oak Park, IL
- Arlington Heights, IL
- Palatine, IL
- Des Plaines, IL
- Hoffman Estates, IL
- Mount Prospect, IL
- Aurora, IL
- Plainfield, IL
- Frankfort, IL
- La Grange, IL
- Tampa, FL
- Los Angeles, CA
Questions about requirements, deposits, or delivery? See the FAQ, read our rental guides, or browse the full fleet.
Before you book
A few local details.
Plan the car, the occasion, and the handoff with our team.
Ask about your plansCan you deliver a car to my address in Winnetka?
Send your dates and the exact home, hotel, office, or venue address in Winnetka. Our concierge checks vehicle availability and coordinates the delivery point, collection arrangements, and any applicable fees before you book.
Are the daily rental price and chauffeur quote the same?
Daily rental rates cover self-drive bookings. Chauffeur service is quoted separately for your vehicle, itinerary, hours, and stops. Tell us which service you want so the team can explain the right price and arrangements.
Which cars can I book for Winnetka?
The cars shown on this page are a selection from the Chicago fleet. Open a vehicle to see its published rental details, then request your dates. A displayed car is not a guarantee of availability for a particular booking.
Can you help me buy, source, or sell a car too?
Yes. Explore our cars for sale or tell us what you want to buy or sell. DDE works with buyers and sellers nationwide. Vehicle location, viewing, sourcing or selling fees, and any transport are discussed separately from rental bookings.
Winnetka
Let's plan your drive.
Share your dates and preferred delivery address in Winnetka. Our team will help you choose the car and plan the handover.