Door-to-Door Time, Station Transfers, Parking, and When a Private Chauffeur Makes the 90-Mile Trip Easier — A Guide for Chicago, the North Shore, and Milwaukee Travelers
Written by the Prestige Lux Limos team — a veteran-owned, licensed and insured Chicago limo company, 10+ years serving Chicagoland. Updated October 2026.
Prestige Lux Limos — veteran-owned, serving Chicago and nearby areas, from The Loop and the North Shore to the western and southern suburbs, with long-distance rides to Milwaukee and across the Midwest. Open 24 hours a day, seven days a week. Rides start at $100, with flat rates and no surge pricing. Call (708) 696-3117 or text (708) 696-3117 · prestigeluxinc@gmail.com · book online.
Quick answer: Chicago to Milwaukee is roughly 90 miles, and you have three realistic ways to make the trip. The Amtrak Hiawatha is about an hour and a half station to station, but you still have to get to Union Station and from the Milwaukee station to where you are going. Driving yourself goes door to door, but you handle the traffic, the parking and the drive home. A car service goes door to door with a private chauffeur, on your schedule, with room for your group and luggage. For a solo traveler living near both stations, the train is hard to beat. For groups, early flights, day trips and anyone who wants to work or rest on the way, a car service is usually the better fit.
How the Amtrak Hiawatha Works
The Amtrak Hiawatha runs several times a day between Chicago Union Station and downtown Milwaukee, with stops in Glenview, Sturtevant and at the Milwaukee airport station. The ride itself takes about an hour and a half, and it is a comfortable way to skip I-94. The trade-off is that the train runs station to station on a fixed timetable. If your trip starts in Naperville or ends at a Milwaukee hotel across town, you need another ride on each end, and your day has to fit the schedule.
How Driving Yourself Works
Driving gives you full control over when you leave and where you go. You also take on the I-94 corridor, which can slow down sharply at rush hour and during construction season, plus parking at your destination and fuel for the round trip. If the trip involves a dinner, a game or an event in Milwaukee, someone also has to stay sober for the drive home.
How a Car Service Works
With our long-distance limo service, a private chauffeur picks you up at your door and drives you directly to your destination in Milwaukee, with no station transfers and no parking. You leave when you want, ride with your whole group in one vehicle, and can work, take calls or rest on the way. Our chauffeur service can be booked by the hour or by the day, so for a day trip the same chauffeur can wait and bring you home that night. For airport trips, our limo service to Milwaukee’s MKE airport covers flights out of Milwaukee.
The Real Difference Is Door-to-Door Time
The train’s ride time is only part of the trip. Add the time to reach Union Station, wait for departure, and get from the Milwaukee station to your hotel or meeting, and the door-to-door total grows. Driving yourself removes the transfers but adds traffic, parking and the work of driving. A car service removes both, which is why the comparison changes so much depending on where you start and end. The closer you live to both stations, the better the train looks. The farther you are from either one, the better a car service looks.
Who the Train Makes Sense For
Solo travelers or couples with light bags, starting near Union Station and heading to downtown Milwaukee, are the clearest fit for the Hiawatha. If your schedule lines up with a departure and you do not need a car in Milwaukee, the train is simple and relaxing.
Who Should Drive Themselves
Travelers who need their own car in Milwaukee for several days, and who are comfortable with the drive and the parking, may prefer to drive. It is also the most flexible option if your plans are likely to change by the hour.
Who Should Book a Car Service
Groups, families with luggage, business travelers who want to work on the way, and anyone starting in the suburbs get the most from a car service. So do Milwaukee travelers catching a flight at O’Hare, where flight tracking and a set pickup time matter, and groups heading up for a game, concert or wedding where no one wants to drive home. Our corporate limo servicehandles Chicago-Milwaukee business trips, and a Sprinter limo seats up to 14 for larger groups. Our luxury SUVs seat 6 to 7.
What a Typical Day Trip Looks Like
Your chauffeur picks you up at home or your office, drives you to your first stop in Milwaukee, and waits or returns at a time you set. After your meeting, game or dinner, you ride home without anyone needing to drive. If you are weighing a full-day booking against separate one-way rides, our guide to what limo hire per day actually costs walks through how to compare them. Travelers connecting to a flight can also book a direct ride to O’Hare with real-time flight tracking.
What Protects Your Trip
Booking ahead is the single most important factor within your control, especially for weekends, game days and early-morning airport runs. Long-distance pricing depends on the route, distance, vehicle and time of service, so call or text for an exact quote. When you book, have your date, pickup and drop-off addresses, group size, luggage and return plans ready.
Frequently Asked Questions
How long is the drive from Chicago to Milwaukee?
Chicago and Milwaukee are roughly 90 miles apart. Your actual drive time depends on traffic and where your trip starts and ends.
How long is the Amtrak train from Chicago to Milwaukee?
The Hiawatha takes about an hour and a half between Chicago Union Station and downtown Milwaukee, with stops in Glenview, Sturtevant and at Milwaukee’s airport station.
Is a car service worth it compared with the train?
It depends on your group and your plans. A car service is usually worth it for groups, travelers with luggage, trips that do not start or end near a station, and times that do not match the train schedule.
Can you take us from Milwaukee to O’Hare for a flight?
Yes. We provide long-distance rides between Milwaukee and Chicago’s airports, with real-time flight tracking for pickups.
Can the chauffeur wait and bring us back the same day?
Yes. Our chauffeur service can be booked by the hour or by the day, so the same chauffeur can wait in Milwaukee and drive you home.
How much does a car service from Chicago to Milwaukee cost?
Pricing depends on the route, distance, vehicle and time of service. Rides start at $100 with flat rates and no surge pricing; call or text (708) 696-3117 for an exact Milwaukee quote.
Which vehicle works best for a group?
Our luxury SUVs seat 6 to 7, and a Sprinter seats up to 14 with room for luggage.
How do I book?
Call or text (708) 696-3117 or book online 24/7. Have your date, pickup and drop-off addresses, group size, luggage and return plans ready.
Find Out Which Option Fits Your Trip
Whether the train, your own car or a car service is right for you depends on where you start, who is coming and what you are doing in Milwaukee, not just the travel time on paper. Book your Milwaukee ride online, call (708) 696-3117 or text (708) 696-3117. Still have questions? Check our FAQ or reach out directly.
Prestige Lux Limos · Chicago & Nearby Areas · (708) 696-3117 · prestigeluxinc@gmail.com · Open 24/7 · Flat rates, no surge pricing
