The short answer
- The Amtrak Hiawatha runs from Chicago Union Station to downtown Milwaukee in about 1 hour 29 minutes, with seven round trips a day and six on Sunday, according to Amtrak.
- Hiawatha trains stop at Glenview, Sturtevant and Milwaukee Mitchell Airport between the two downtown stations.
- By road, the Loop to Fiserv Forum is about 89 miles and 110 minutes without traffic; from Northbrook, the Milwaukee Art Museum is about 85 minutes.
- The train is the better choice for one or two people going downtown to downtown; a car wins for groups, suburban starts, American Family Field and late returns.
Planning this trip? See the price online in a few steps, or talk it through with us any hour.
Chicago to Milwaukee by train or drive: the comparison
The two downtowns are about 90 miles apart, and both the train and the road take roughly the same time between them. The difference is everything around that core: getting to Union Station, getting from the Milwaukee station to where you are actually going, parking, and how the night ends.
Fares are left out of the table on purpose. Train tickets are priced per person and vary with the date, while a car service is priced per vehicle, so compare both for your actual day and headcount; Amtrak's site shows the fare for each train.
| Amtrak Hiawatha | Drive yourself | Car service | |
|---|---|---|---|
| Core trip time | About 1 h 29 min, station to station | About 110 min, Loop to Fiserv Forum | About 110 min, door to door |
| Starts at | Union Station or Glenview | Your door | Your door, hotel or O'Hare |
| Ends at | Downtown Milwaukee or MKE airport | Wherever you park | The venue entrance |
| Schedule | Seven round trips a day, six on Sunday | Any time | Any time, 24/7 |
| After a late event | Depends on the last train | Someone has to stay sober and drive | The car waits and drives you back |
| Best for | One or two travelers, downtown to downtown | Flexible day trips | Groups, suburbs, games and concerts |
The Amtrak Hiawatha, stop by stop
The Hiawatha is Amtrak's Chicago–Milwaukee corridor, run with the Illinois and Wisconsin departments of transportation over about 86 miles. Amtrak lists the trip at 1 hour 29 minutes and seven round trips daily, six on Sunday. Coach seats are reserved, every train has a Quiet Car, and business class is offered on only two of the trains.
In Milwaukee the train ends at Milwaukee Intermodal Station, 433 West St. Paul Avenue, which is also the western end of The Hop streetcar's M-Line. Amtrak's Borealis and Empire Builder also call there once a day each on their way north and west.
Because coach seats are reserved, book the specific train you want rather than turning up for the next one, and check the return times before you commit to a late event.
- Chicago Union Station, downtown.
- Glenview, the convenient boarding point for the North Shore.
- Sturtevant, Wisconsin.
- Milwaukee Airport, the rail station for Milwaukee Mitchell International.
- Milwaukee Intermodal Station, downtown.
When the train is the better choice
Take the Hiawatha when you are one or two people, you start near Union Station or Glenview, and you are going downtown: a meeting, a hotel near the Third Ward, or a Bucks game at Fiserv Forum. It also works well for a flight out of Milwaukee Mitchell, since the train stops at the airport.
The train keeps the trip off I-94 at rush hour, and you can work or rest the whole way. We would rather say that plainly than sell a car to someone who does not need one.
North Shore travelers have an extra advantage: boarding at Glenview skips the trip into Union Station entirely. And anyone flying from Milwaukee Mitchell can ride the same train to the airport stop instead of driving the length of I-94.
When a car makes more sense
The case for the road grows with the size of the group and the distance from Union Station. A family from Schaumburg would first spend time getting downtown to board; by car, the Historic Third Ward is about 105 minutes from Schaumburg without traffic. From O'Hare straight off a flight, Fiserv Forum is about 100 minutes.
Some venues are simply not near the station. American Family Field, where the Brewers play, is about 115 minutes from the Loop by car and about 10 minutes from Fiserv Forum, so a train trip to a ballgame still needs another ride at the Milwaukee end. Summerfest at Henry Maier Festival Park on the lakefront is about 115 minutes from the Loop, and a car can drop the group near the gates.
Then there is the end of the night. After a concert or an extra-time game, a group that came by train is watching the clock for the last departure; a group with a car service walks out to an agreed pickup spot and goes home.
Groups of six or more: where the train math changes
Train tickets are per person, and so is the trip to Union Station. A group of eight from different suburbs has to meet downtown first, ride together, then find enough taxis or rideshares in Milwaukee to reach the venue. Coming home, the whole group has to make the same train, which is the hard part after a game or a long dinner.
A single vehicle collects people where they are and keeps them together all day. A Sprinter limo seats 14, an Executive Sprinter 14 in captain's chairs for a client day, and the party buses 25 or 35. The vehicle is priced as a whole, so its cost per rider falls as the group grows, while every train fare stays the same.
A Bucks, Brewers or Summerfest day, planned
Most group trips to Milwaukee are built around a fixed start time. Plan back from it.
- Fix the event time and add a margin for I-94 traffic out of Chicago.
- Set the pickup about 110 minutes plus that margin before you want to arrive, longer from the western suburbs.
- Agree on one drop-off point at the venue and one pickup point for afterwards.
- Book a round trip with the car waiting, or hourly service if there are stops before or after.
- Tell the chauffeur if the group splits up, so everyone knows where to meet.
Driving yourself: the honest trade-offs
Driving gives you the same 110-minute core trip as a car service, and it is the cheapest option for a family that already owns the car. The costs are parking in downtown Milwaukee on an event night, the rush-hour stretch of I-94 out of Chicago, and one person who cannot drink and has to drive about 90 miles home at the end.
For a quiet day trip to the Milwaukee Art Museum or the Harley-Davidson Museum, driving yourself is perfectly sensible. For a birthday, a bachelor party or a playoff game, the designated driver is usually the person who regrets it.
If you do drive, check the venue for event parking before you leave, and give yourself extra time on the Chicago end of the trip, where the traffic is heaviest.
How a car service trip to Milwaukee works
There are three ways to book it, and each has a price set before you book. A one-way ride suits a hotel stay or a flight from Milwaukee. A round trip with the car waiting suits a game or a concert. Hourly service, with a 2-hour minimum, suits a day with several stops, such as lunch in the Third Ward, the museum and dinner.
The vehicle follows the group. An Escalade seats 6, a Sprinter limo 14, and a party bus up to 35. Our Chicago to Milwaukee page lists drive times to each venue, and the Chicago to Milwaukee airport page covers flights from MKE, about 105 minutes from the Loop without traffic.
Tell us the event and its start time when you book. The pickup is then set from the real drive time from your address, with room for traffic, rather than guessed.
