Long Distance & Intercity Transfers
Chicago to Milwaukee starts at $195 by luxury sedan. Indianapolis from $375, Detroit from $495. All prices are flat rates including tolls and fuel. Door-to-door service, WiFi included.
Skip the train or short-haul flight. Travel in comfort between Chicago and major Midwest cities with flat-rate pricing, WiFi, and door-to-door convenience.
Popular Destinations
Flat-rate pricing from Chicago to major Midwest cities. One-way or round-trip available.
Milwaukee, WI
92 miles | 1.5 - 2 hours
Madison, WI
147 miles | 2.5 - 3 hours
Indianapolis, IN
185 miles | 3 - 3.5 hours
Detroit, MI
283 miles | 4 - 4.5 hours
Grand Rapids, MI
180 miles | 3 - 3.5 hours
St. Louis, MO
297 miles | 4.5 - 5 hours
Don't see your destination? We travel anywhere in the Midwest.
Call for Custom QuoteWhy Choose Car Service Over Flying?
For many Midwest destinations, luxury car service beats the alternatives.
Door-to-Door Service
No parking at airports or train stations. We pick you up and drop you off exactly where you need to be.
Productive Travel Time
WiFi, power outlets, and privacy let you work, take calls, or prepare for meetings during the drive.
Flexible Scheduling
Depart when you want, not when the train or flight is scheduled. Perfect for tight business schedules.
No TSA, No Delays
Skip airport security and boarding processes. Just get in and go - often faster door-to-door than flying.
Group Economics
For 2-4 travelers, car service often costs less than multiple flight tickets, especially with luggage.
Flat Rate Certainty
Your quoted price is your final price. No surge pricing, no tolls to figure out, no parking fees.
Door-to-Door Time Comparison
When you factor in airport time, car service is often just as fast - with more comfort.
Long Distance FAQs
How does long distance pricing work?
We charge flat rates based on destination, not metered rates. The price you're quoted includes the entire trip - no tolls, fuel surcharges, or wait time fees. It's truly all-inclusive.
Can the driver wait while I have meetings at my destination?
Yes, we offer point-to-point or round-trip service. For round-trips, your chauffeur waits during your meeting (hourly wait rate applies) or we can arrange a pickup time. Many clients prefer separate one-way bookings for flexibility.
Is long distance service available 24/7?
Absolutely. We regularly transport clients on early morning trips to catch flights at other airports, late-night returns from events, and everything in between. 24/7/365 availability.
What happens if there's traffic or weather delays?
Your flat rate is locked in regardless of traffic conditions. We monitor weather and traffic patterns to ensure timely arrival, building in appropriate buffers for your schedule.
Can I stop along the way?
Yes, we can accommodate reasonable stops (rest breaks, quick meals) within the trip. Extended stops or significant detours may incur additional charges discussed in advance.
How does this compare to train or flying for business travel?
For Milwaukee and Indianapolis, door-to-door car service is often faster than flying when you factor in airport time. You also gain productive work time, WiFi, and privacy. For groups of 2+, it's often more economical too.
Ready for Comfortable Intercity Travel?
Book your long distance transfer now or call for a custom quote.