Why should I choose a professional car service over a rideshare app?

Choosing a professional service like ours provides a fundamentally different level of service focused on safety, reliability, and professionalism. Unlike rideshare services, our chauffeurs are professionally trained, vetted, and commercially licensed and insured. Our vehicles are meticulously maintained for safety and comfort, not personal use. With us, you get a pre-scheduled, guaranteed ride with a dedicated professional, ensuring peace of mind, especially for important events like airport transfers or corporate meetings.

Why does professional car service cost more than a rideshare?

The cost of our service reflects the professional standards we uphold. This includes rigorous vehicle maintenance, comprehensive commercial insurance policies that protect you, professional chauffeur training, and the logistical support required to guarantee on-time service. You are not just paying for a ride; you are investing in reliability, safety, and a seamless, stress-free experience from start to finish.

What is your cancellation policy?

Our cancellation policy varies by vehicle to ensure fairness and availability: Sedans & SUVs: Require a 2-hour cancellation notice. Premium Luxury Sedans & SUVs: Require a 3-hour cancellation notice. Stretch Limos & Sprinter Vans: Must be canceled at least 48 hours in advance for a full refund, or 24 hours in advance for a 50% refund. Vehicles seating more than 14 passengers (Buses, etc.): Require a 5-day cancellation notice. Weddings and other large special events follow the cancellation policy of the largest vehicle booked for the event.

Do you offer worldwide transportation services?

Yes. We partner with a network of vetted, trusted affiliates to provide the same level of service you expect from Legacy almost anywhere in the world. We handle all the logistics, so you have a single point of contact for all your ground transportation needs. Please note that our online system only prices trips for the Chicago area; for all other markets, you will receive an updated invoice from our team.

Can I leave my belongings in the vehicle during my event?

This depends on your booking type. For Hourly Charters, the vehicle is reserved exclusively for you, and you are welcome to leave your belongings inside. For Point-to-Point transfers, the chauffeur may have other trips, so we cannot guarantee the vehicle can store your items. Please confirm with us when booking.

Is gratuity included in my quote?

Gratuity is entirely at your discretion. You are welcome to tip your chauffeur in cash or request to have a tip added to your final bill. For your convenience, we can add a customary 15% or any amount you wish. For larger groups in vehicles that seat more than 8 passengers, a minimum 15% gratuity is automatically included to streamline the tipping process.

What is your wait time policy?

We provide complimentary wait time for all trips: Airport Arrivals (Domestic): 60 minutes of complimentary wait time after your flight has gated. Airport Arrivals (International): 90 minutes of complimentary wait time after your flight has gated. All Other Pickups: 10 minutes of complimentary wait time after your scheduled pickup time. For non-airport pickups, wait time beyond the 10-minute grace period is billed at $10 for the first 10 minutes, plus $1 per minute thereafter. If wait time exceeds 60 minutes, the full hourly minimum for that vehicle will be charged.

Do you provide child car seats?

Yes, we provide child car seats free of charge, but they must be requested in advance. While we provide the seats, clients are encouraged to perform the final installation to ensure it meets their standards. There is no specific limit to the number of car seats per vehicle, as long as it is reasonable and safe for the vehicle's capacity.

Pets are welcome in our vehicles. We ask that you notify us in advance and that all pets remain secured in a carrier or with a specialty pet seatbelt for their safety. To avoid any potential fees, please ensure your pet is well-groomed. Excessive fur or any damage caused to the vehicle's interior may result in an appropriate cleaning or repair charge.

What happens if my flight is delayed?

We monitor all incoming flights in real-time. Whether your flight is early, on time, or delayed, your chauffeur will be waiting for you when you land. You do not need to contact us to report a flight delay.

What is your cleaning/damage policy?

We maintain our vehicles in pristine condition. Any client-caused damage that alters the interior or exterior of the vehicle will be billed for the full cost of repairs. An excessive mess (e.g., spills of sugary drinks, alcohol, food stains) that requires the vehicle to be taken out of service for a deep cleaning will incur a cleaning fee. Our drivers visually inspect and photograph vehicles before and after every trip.

Frequently Asked Questions

Your questions, answered. Find information on our policies, services, and what to expect when you book with Legacy.

The Legacy Difference

Why should I choose a professional car service over a rideshare app?
Choosing a professional service like ours provides a fundamentally different level of service focused on safety, reliability, and professionalism. Unlike rideshare services, our chauffeurs are professionally trained, vetted, and commercially licensed and insured. Our vehicles are meticulously maintained for safety and comfort, not personal use. With us, you get a pre-scheduled, guaranteed ride with a dedicated professional, ensuring peace of mind, especially for important events like airport transfers or corporate meetings.
Why does professional car service cost more than a rideshare?
The cost of our service reflects the professional standards we uphold. This includes rigorous vehicle maintenance, comprehensive commercial insurance policies that protect you, professional chauffeur training, and the logistical support required to guarantee on-time service. You are not just paying for a ride; you are investing in reliability, safety, and a seamless, stress-free experience from start to finish.

Booking & Reservations

What is your cancellation policy?
Our cancellation policy varies by vehicle to ensure fairness and availability:

Sedans & SUVs: Require a 2-hour cancellation notice.
Premium Luxury Sedans & SUVs: Require a 3-hour cancellation notice.
Stretch Limos & Sprinter Vans: Must be canceled at least 48 hours in advance for a full refund, or 24 hours in advance for a 50% refund.
Vehicles seating more than 14 passengers (Buses, etc.): Require a 5-day cancellation notice.

Weddings and other large special events follow the cancellation policy of the largest vehicle booked for the event.
Do you offer worldwide transportation services?
Yes. We partner with a network of vetted, trusted affiliates to provide the same level of service you expect from Legacy almost anywhere in the world. We handle all the logistics, so you have a single point of contact for all your ground transportation needs. Please note that our online system only prices trips for the Chicago area; for all other markets, you will receive an updated invoice from our team.
Can I leave my belongings in the vehicle during my event?
This depends on your booking type. For Hourly Charters, the vehicle is reserved exclusively for you, and you are welcome to leave your belongings inside. For Point-to-Point transfers, the chauffeur may have other trips, so we cannot guarantee the vehicle can store your items. Please confirm with us when booking.

Pricing & Fees

Is gratuity included in my quote?
Gratuity is entirely at your discretion. You are welcome to tip your chauffeur in cash or request to have a tip added to your final bill. For your convenience, we can add a customary 15% or any amount you wish. For larger groups in vehicles that seat more than 8 passengers, a minimum 15% gratuity is automatically included to streamline the tipping process.
What is your wait time policy?
We provide complimentary wait time for all trips:

Airport Arrivals (Domestic): 60 minutes of complimentary wait time after your flight has gated.
Airport Arrivals (International): 90 minutes of complimentary wait time after your flight has gated.
All Other Pickups: 10 minutes of complimentary wait time after your scheduled pickup time.

For non-airport pickups, wait time beyond the 10-minute grace period is billed at $10 for the first 10 minutes, plus $1 per minute thereafter. If wait time exceeds 60 minutes, the full hourly minimum for that vehicle will be charged.

Service & Fleet

Do you provide child car seats?
Yes, we provide child car seats free of charge, but they must be requested in advance. While we provide the seats, clients are encouraged to perform the final installation to ensure it meets their standards. There is no specific limit to the number of car seats per vehicle, as long as it is reasonable and safe for the vehicle's capacity.
Can I bring my pet?
Pets are welcome in our vehicles. We ask that you notify us in advance and that all pets remain secured in a carrier or with a specialty pet seatbelt for their safety. To avoid any potential fees, please ensure your pet is well-groomed. Excessive fur or any damage caused to the vehicle's interior may result in an appropriate cleaning or repair charge.
What happens if my flight is delayed?
We monitor all incoming flights in real-time. Whether your flight is early, on time, or delayed, your chauffeur will be waiting for you when you land. You do not need to contact us to report a flight delay.
What is your cleaning/damage policy?
We maintain our vehicles in pristine condition. Any client-caused damage that alters the interior or exterior of the vehicle will be billed for the full cost of repairs. An excessive mess (e.g., spills of sugary drinks, alcohol, food stains) that requires the vehicle to be taken out of service for a deep cleaning will incur a cleaning fee. Our drivers visually inspect and photograph vehicles before and after every trip.