Quick answer: Long-distance car service from Chicago’s south suburbs to Milwaukee, South Bend or Lake Geneva typically costs $380 to $640 one way, and trips to Madison or Indianapolis run about $570 to $960, depending on whether you ride in a sedan, an S-Class or a luxury SUV. Prices are before gratuity and tolls. Because the car has to return home, one-way long-distance trips are billed on the time for the full round trip.

Written by the Emily’s Limousine Service team. We are based in Orland Park and have driven executives, families and travelers across Chicago and the Midwest for more than 25 years. The estimates below use our real starting rates.

Sometimes the best way to get to another city is not a flight or a four-hour drive of your own. A private car with a professional chauffeur gets you there door to door, lets you work or rest on the way, and removes the parking, the rental counter and the drive home after a long day. This guide covers what long-distance car service from Chicago costs, the most popular routes, and how to choose the right vehicle.

Long Distance Car Service From Chicago: Estimated Rates

Each estimate starts in Orland Park and multiplies our starting hourly rate by the round-trip drive time. Your exact quote depends on your pickup address, drop-off address and travel time of day.

Estimates are before gratuity (18 to 20%), tolls and any parking or airport fees. For longer runs to cities such as Detroit, St. Louis or Des Moines, we quote each trip individually. See our pricing page for every vehicle and rate.

One Way, Round Trip or Wait and Return

Long-distance trips are booked in three ways, and picking the right one saves money.

One Way

You ride to your destination and the car returns to Chicago empty. Because the chauffeur and vehicle are tied up for the drive home, the trip is billed on round-trip time. One way works best for airport drop-offs, campus move-ins and relocations.

Round Trip on Two Days

If you are staying a few days, book a drop-off on your arrival day and a separate pickup on your return day. Each leg is billed as its own round trip, which is still far cheaper than keeping a car and driver for the whole stay.

Wait and Return on the Same Day

For a meeting, a campus visit or a family event, the chauffeur waits and drives you home the same day. Example: a 3-hour drive to Indianapolis, a 4-hour meeting and a 3-hour drive home is a 10-hour booking. In an Escalade at $160 per hour, that is $1,600 before gratuity and tolls, with no rental car, no parking and no tired drive home in the dark.

Popular Long-Distance Routes

Chicago to Milwaukee Car Service

Milwaukee is the most requested long-distance run we make. Business travelers head to meetings downtown and in the Third Ward, fans go to Brewers and Bucks games, and families visit for weddings, graduations and holidays. The drive up I-94 takes about 2 hours from the south suburbs, though Friday afternoon traffic through the north suburbs can add 30 minutes or more.

Car Service to Milwaukee Airport (MKE)

Some travelers fly out of Milwaukee Mitchell instead of O’Hare or Midway, often because a nonstop route or fare works better for their trip. A private car makes that choice easy: you are picked up at home, your luggage is handled, and you are dropped at the terminal without paying for long-term parking in another state. For flights out of Chicago, see our Chicago airport transfers, O’Hare limo service and Midway limo service pages.

Chicago to South Bend and Notre Dame

Parents’ weekends, campus move-in and move-out, graduation and football Saturdays keep this route busy from August through May. South Bend is on Eastern Time, one hour ahead of Chicago, so set pickup times from the event start time in Eastern Time. The route uses the Indiana Toll Road. For larger groups heading to a game, our guide to charter bus trips from Chicago covers coaches and Sprinters.

Chicago to Madison

Madison runs center on the University of Wisconsin and the state capitol: campus visits, Badgers games, graduations and government meetings. At about 2 hours 45 minutes each way, a same-day wait and return works well for a single meeting or event.

Chicago to Indianapolis

Conventions, corporate offices, Colts games and racing events bring travelers to Indianapolis. Like South Bend, Indianapolis is on Eastern Time. A private car gives an executive about 3 hours of quiet work time each way, which is often worth more than the time saved by flying once you count security lines and airport transfers on both ends.

Lake Geneva Getaways

Couples, golf groups and wedding parties heading to Lake Geneva resorts book a drop-off and a pickup a few days later. For larger wedding groups, pair a luxury SUV for the couple with a Sprinter van for family and friends.

Which Vehicle Is Right for a Long Trip?

• Cadillac XTS sedan: Up to 4 passengers. The most economical choice for a solo traveler or couple with standard luggage.
• Mercedes-Benz S-Class: Up to 4 passengers. The quietest and most refined ride for executives who want to work or rest. Learn more about our S-Class limo service.
• Cadillac Escalade, Lincoln Navigator or Chevy Suburban: Up to 6 passengers with room for luggage. The best fit for families, golf bags and winter travel. Our luxury SUV service guide covers each model.
• Executive Jet Sprinter: Up to 10 passengers in executive seating, ideal for a leadership team traveling together. See our Executive Sprinter page.

Why Choose a Private Car Over Driving, Flying or Rideshare

• Door to door: No airport security, no rental counter and no searching for parking at the other end.
• Productive time: Take calls, answer email or sleep while a professional chauffeur handles the road.
• Predictable pricing: Your quote is set before the trip. Long rideshare trips can be hard to book, and drivers may decline rides that leave them far from home.
• Safety in winter: Our chauffeurs drive Midwest winters every year in well-maintained vehicles, so you are not driving on unfamiliar roads after dark.

For a full comparison, read black car service vs. rideshare in Chicago.

Corporate Accounts for Regular Long-Distance Travel

Companies that send people between Chicago, Milwaukee and Indianapolis every month can set up a corporate account with invoicing and consistent vehicles. Office managers and executive assistants can book, track and change trips in one place. Learn more about our corporate limousine service and read our corporate transportation guide for the south suburbs.

What Your Long-Distance Quote Includes

What to Have Ready When You Book

• Pickup address and date
• Destination address, airport terminal or venue
• Time you need to arrive, noting Eastern Time for South Bend and Indianapolis
• Flight details for airport trips
• Number of passengers and bags, including golf bags or oversized luggage
• Trip type: one way, round trip on two days, or wait and return

Long Distance Car Service FAQ

How much is a car service from Chicago to Milwaukee?
From the south suburbs, a one-way trip to downtown Milwaukee costs about $380 in a sedan, $560 in an S-Class and $640 in an Escalade or Navigator at our starting rates, before gratuity and tolls.

Why is a one-way long-distance trip billed for the return?
The chauffeur and vehicle have to drive back to Chicago, so the trip uses the same time as a round trip. If you are staying a few days, separate drop-off and pickup trips cost far less than keeping the car and chauffeur with you.

Can the chauffeur wait while I attend a meeting?
Yes. Wait and return bookings are billed hourly for the full day, including the time the chauffeur waits for you.

Do you drive to cities outside Illinois?
Yes. We regularly drive to Wisconsin and Indiana, and we quote longer Midwest trips individually.

How far in advance should I book?
Book at least 48 hours ahead for long-distance trips, and 1 to 2 weeks ahead for graduation weekends, football Saturdays and holidays.

Is a car service to another city cheaper than flying?
For one traveler, flying is often cheaper on fare alone. For two to six people sharing one vehicle, a private car is often competitive once you add airfare, bags, parking and ground transportation at both ends.

Is gratuity included?
A standard chauffeur gratuity of 18 to 20% may be added unless it is already included in your quote. Your quote shows the full total before you book.

What is your deposit and cancellation policy?
A deposit reserves your vehicle and locks in your rate, and the balance is due before or on the day of service. Cancellations made with sufficient notice are eligible for a refund of the deposit, while late cancellations may be subject to a fee.

How can I pay?
We accept major credit cards and cash. Corporate accounts can be invoiced for recurring travel.

Can we make a stop on the way?
Yes. You can add a stop to pick up a colleague, grab a meal or run an errand. Each stop adds a little time, which we include in your quote.

Can I book a ride for someone else?
Yes. Parents often book rides for students, and assistants book for executives. Just give us the passenger’s name and phone number so the chauffeur can reach them.

How much luggage fits in a luxury SUV?
An Escalade, Navigator or Suburban seats up to 6 and is the best choice when you have several suitcases, golf bags or winter gear. Tell us your bag count when you book so we send the right vehicle.

Are you licensed and insured?
Yes. Emily’s Limousine Service is licensed and fully insured, and our chauffeurs are professional drivers focused on punctuality and discretion.

Book Your Long-Distance Car Service

Tell us where you are going, when you need to arrive and how many people and bags are traveling, and we will quote the right vehicle and schedule. Explore our black car service and chauffeur service, then request a free quote or call Emily’s Limousine Service in Orland Park at (312) 446-7505. We are available 24/7.