Frequently Asked Questions
Your questions, answered. Find information on our policies, services, and what to expect when you book with Legacy.
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The Legacy Difference
Why choose Legacy over a rideshare app in Chicago?
Unlike unpredictable rideshare apps, we provide a guaranteed, dependable black car service. Our vehicles are company-owned and inspected daily. We rigorously vet, background-check, and drug-test our professional chauffeurs. You get safety and consistency that an app simply cannot provide, including our 10-minute early arrival guarantee.
Are you fully insured and licensed?
Yes. We maintain commercial insurance coverage that exceeds city and state requirements to guarantee your safety. We also operate with an A+ rating from the Better Business Bureau (BBB) and are active members of the National Limousine Association (NLA).
What areas do you service?
While we are headquartered in Evergreen Park, we provide transportation across the entire Chicago metropolitan area. We also specialize in long-distance travel across the Midwest, frequently driving clients to Milwaukee, Indianapolis, Madison, and South Bend.
Is my chauffeur guaranteed to show up?
Absolutely. When you book with us, your ride is locked in. We track your reservation, dispatch your vehicle well in advance, and guarantee your chauffeur will be on-site 10 minutes early. You will never be left stranded.
Booking & Reservations
Do you offer corporate accounts and billing?
Yes. We offer streamlined corporate accounts for businesses, executive assistants, and travel managers. A corporate account provides simplified monthly invoicing, priority dispatching, and a dedicated portal to manage multiple travelers and itineraries at once.
How far in advance should I book my car service?
We recommend booking at least 24 hours in advance to guarantee your preferred vehicle. However, our dispatch team operates 24/7, and we can often accommodate last-minute requests. For large events like weddings and proms, we suggest booking 3 to 6 months early.
Can I modify my reservation after booking?
Yes, you can easily make changes in three ways:
Client Login: Click the "Client Login" button on our website. Enter your phone number to receive a secure passcode. Once logged in, you can view or modify all current and past reservations.
Email Link: Use the direct link provided in your reservation confirmation email.
By Phone: For last-minute changes, call our dispatch team at +1 (708) 968-4226. (Note: Changes to vehicle type or time are subject to availability.)
What happens if my flight is cancelled?
Please notify us as soon as possible. If we have not yet dispatched the chauffeur, there is no charge. While we monitor flights, a full cancellation requires your direct confirmation.
What is the cancellation policy for car service?
For standard sedan and SUV transfers, we require a 2-hour notice prior to pickup. For Sprinter Vans, buses, and special events, cancellation terms vary and are explicitly outlined in your contract.
Pricing & Fees
Are there hidden fees or taxes?
No. We run an honest business with transparent pricing. Every trip has a standard $4.50 tax added to it. Any potential extra charges (like excessive wait times or unplanned stops) will be billep appropriately.
Is gratuity included in the price?
For vehicles seating 8 or more passengers (Stretch Limos, Sprinters, Buses), a customary 20% gratuity is automatically applied to compensate the chauffeur. For Sedans and standard SUVs, gratuity is completely at your discretion.
What is your wait time policy?
We provide complimentary wait time to ensure a stress-free pickup:
- Domestic Airport Arrivals: 60 minutes of free wait time after your flight has gated.
- International Airport Arrivals: 90 minutes of free wait time after your flight has gated.
- Standard Pickups: 10 minutes of free wait time after your scheduled time.
After the grace period (hourly charters excluded), wait time is billed at $10 for the first 10 minutes, plus $1 per minute after that.
If wait time exceeds 60 minutes, the full hourly minimum for that vehicle will be charged.
Is there a cleaning fee?
We maintain our vehicles in excellent condition. Any damage or excessive mess (e.g., major spills, food stains) that requires the vehicle to be taken out of service for deep cleaning will result in an additional fee. Our chauffeurs inspect and photograph vehicles before and after every trip.
Can we make stops during a long-distance trip or hourly charter?
Yes. For hourly as-directed charters, you have the vehicle for the duration of your booking and can make as many stops as you need. For flat-rate point-to-point or long-distance transfers (like a trip to Milwaukee or Notre Dame), brief restroom stops are accommodated, but extended or secondary stops must be requested in advance and may incur a small additional routing fee.
Service & Fleet
Do you track flights at O'Hare and Midway?
Yes. We monitor all inbound flights into O'Hare (ORD), Midway (MDW) and Private FBOs. If your flight is delayed or early, we automatically adjust your pickup time so your chauffeur is there when you land.
What happens if my flight is delayed?
Because we track your exact flight number, our system automatically adjusts your pickup time based on your actual arrival. You are never charged extra for wait time caused by an airline delay.
How do I meet my chauffeur at the airport?
We offer two options. Our standard service is a prompt curbside pickup—your chauffeur will text you when you land and meet you at the designated terminal door. If you prefer, you can request an inside "Meet and Greet" for an additional fee, where your chauffeur will wait at baggage claim with a digital name sign to assist with your luggage.
Do you provide child car seats?
Yes, we provide child car seats for an additional fee. They must be requested in advance during the booking process. While we provide the seats, parents are encouraged to perform the final installation to ensure their child's safety.
Can I bring my pet?
Pets are welcome in our vehicles. We ask that you notify us in advance and ensure all pets remain secured in a carrier or with a pet seatbelt. To avoid cleaning fees, please ensure your pet is well-groomed before the ride.
What if I have oversized luggage like golf clubs or skis?
While our Executive Sedans easily hold standard suitcases, oversized items require an Executive SUV or a Sprinter Van to ensure safe transport. Please let our dispatch team know about any oversized items when booking so we can guarantee the correct vehicle size for your trip.



