Quick answer
Self-drive if you qualify and the day is about driving; chauffeured if the day is about arriving. Self-drive requires approval for the selected vehicle, a valid driver's license, and qualifying full-coverage insurance (minimum limits $100K/$300K/$100K), and the car's refundable security deposit — $1,000–$7,500 depending on the vehicle. A chauffeured booking puts a professional driver in a confirmed suitable DDE vehicle, so the age minimum and self-drive insurance requirement don't apply to your party — which is why it's the route for younger guests of honor, weddings, and every prom reservation, where a private driver is always included. Daily rental rates are starting self-drive prices. Chauffeured packages are quoted separately around your vehicle, route and hours through our chauffeur service.
What self-drive requires
Self-drive is a standard DDE rental: you take the keys, and the checklist applies. Confirm the exact vehicle’s minimum age and driver eligibility with DDE. The general policy starts at 21 with younger drivers considered case by case, and individual listings may differ. You must hold a valid driver's license and carry full-coverage insurance — comprehensive, collision, and liability with minimum limits of $100K/$300K/$100K — that covers the rental vehicle. Our team verifies license and coverage before every handover, and the refundable deposit ($1,000–$7,500 by vehicle, shown on each car's page) is authorized before handover and released 24–72 hours after the rental ends. The complete rundown, payment methods included, is in our requirements guide.
How chauffeured bookings work
Every chauffeured journey pairs a vetted professional driver with the right vehicle from the fleet — discreet, punctual, and impeccably presented. From a single executive transfer to full event logistics, the itinerary is coordinated end to end: airport pick-ups at O'Hare, Midway, and Tampa International come with flight tracking and meet-and-greet, so your driver is there no matter the delay. Because every route and schedule is different, chauffeured packages are quoted individually — tell the concierge your occasion, route, and hours and the quote covers the whole plan.
When the chauffeur is the answer
- You're too young to self-drive, or your insurance doesn't qualify. The self-drive checklist doesn't apply to chauffeured passengers — it's the route into the fleet for everyone the requirements exclude.
- Weddings. Most couples choose a chauffeured arrival so delivery, timing, and the entrance are handled — details on the wedding car rental page.
- Prom. Not optional, by design: every prom reservation includes a professional private driver.
- Airport and executive runs. Flight-tracked pick-ups and a driver who waits, so the schedule bends to you.
- The back seat is the point. In a Rolls-Royce Ghost or Cullinan, being driven is the full experience — the Rolls-Royce rental page covers both.
When self-drive is the answer
Some cars lose the plot with a driver in them. The Porsche 911 GT3 RS, the Porsche 718 Boxster, and the Lamborghini Huracán EVO Spyder are driver's cars — the wheel is the product. If that's the rental you're planning, our guide to the best scenic drives near Chicago maps routes that earn the rate, and the Porsche rental page covers the current listings for the badge. Self-drive also suits multi-day rentals where the car is yours for the weekend — errands, dinners, and the long way home included.
What each costs
Daily rental rates describe self-drive bookings. Chauffeur service is quoted separately for the vehicle, route and hours. Ask for the complete charges, including any applicable delivery, waiting time, additional stops, taxes or other fees. Chicago delivery and collection arrangements are confirmed for your addresses. Do not add a daily self-drive price to an assumed driver fee and treat it as a confirmed package. For the fleet-wide starting-rate reference, see the 2026 pricing guide.
The fine print, either way
A few terms are identical whichever way you rent. Payment: we accept debit and credit cards, ACH transfer, Zelle, Venmo, Cash App, cryptocurrency, and cash, with the payment method and process confirmed for your booking. Deposits: for self-drive, the refundable hold is authorized on the day of your reservation and released 24–72 hours after the rental ends, once the car returns in its original condition. Cancellations: rentals are not refunded, but cancelling more than 72 hours before your reservation earns a credit toward a future booking — worth knowing if a wedding or event date might move. When in doubt, tell the concierge the plan; terms are easier to work with before the date than after it.
