Travel By Train to Milwaukee

  James  5 mins read.

Travel By Train

If you live anywhere in the Midwest taking a train to Milwaukee is sometimes easier than flying. It is often possible to get a great deal of reading, writing, and other work done while riding the train.

Using a combination of WiFi access on the train, and tethering to your phone you should be able to access the internet during your trip. This access can be a bit intermitent, yet is generally sufficient for emailing and basic web browsing.

I recommend you avoid any connections other than the Hiwatha commuter link between Chicago and Milwaukee.

I strongly recommend a roomette or at least business class if traveling for more than a few hours. A first class ticket comes with free meals, which helps to make up for the additional cost. On long-distance trains with multiple levels, the upstairs roomettes generally have a much better view and make it easier to access the rest of the train. The only downside is they are less handicap accessible than the lower levels.

The Milwaukee Amtrak station is at the Milwaukee Intermodal Station which is a few blocks away from the various Milwaukee downtown hotels. Although you could easily walk to your hotel if traveling light, a short Uber or taxi ride is probably a better idea with heavy bags, or if arriving late at night.

Outside of the Midwest, it generally makes far more sense to fly.

To obtain a Certified LeSS Practioner certification you must attend the entire course. As a practical matter this often requires spending an additional night in a hotel, and returning home the next day. Please plan accordingly.

Chicago to Milwaukee

The Hiawatha is a particularly easy travel choice if you are coming from downtown Chicago. The Hiwatha only takes one hour and fifteen minutes to travel between downtown Chicago and downtown Milwaukee. This even faster than the two hours it takes to drive, assuming good traffic.

When you look at the Hiawatha schedule you will see multiple routes per day in both directions. Almost all of these are proper trains with large comfortable seats, even though technically “coach” class. The one notable exception is train #8307 which is indicated as “BUS” on the schedule. I strongly advise avoiding the “BUS” version of the train in favor of the real train.

Elsewhere in the Mid-West

In most cases train travel to Milwaukee involves taking a train to Chicago, and then taking the Hiawatha schedule to Milwaukee. The only notable expection is travel on the Empire Builder route which passes through St. Paul, and Milwaukee, on its way to Chicago.

The Amtrak website can be a bit clunky to navigate. The following links can be helpful.

  • Amtrak Home Page with a booking feature comparable to most airline websites.
    • The search results will be less confusing if you already know which train routes will work best for you.
    • The search engine seemingly tries to ensure a two hour layover for any connections. It is therefore important to know you can typically use a later Hiawatha train ticket to ride an earlier Hiawatha train.

  • Amtrak System Map

  • Summary page of every Amtrak route
    • The schedules link in the navigation bar is especially useful for identifying your best option for travel to Union Station in Chicago (CHI).
    • By comparing the Chicago arrival and departure times of the various trains into Chicago, with the Hiawatha train schedule it becomes much easier to understand your options.

Summary of Mid-West Train Options

With the exception of the Empire Builder, each of these routes will require connecting to the Hiawatha in Chicago. The schedules link on the Amtrak routes page will make it easy to see the departure and arrival times in both directions.

Train Schedule Reliability

In my experience, the schedule reliability of a long-distance Amtrak train becomes increasingly worse the farther one gets from the origin. A train such as the Texas Eagle will consistently leave Chicago on-time as it begins its journey towards Los Angles. In contrast, if you are attempting to go from Dallas to Chicago on the north-easterly bound Texas Eagle which originates in Los Angeles, don’t expect the train to pass through Dallas on schedule.

When taking a long-distance train from the mid-point it is best to plan to check the train status during its journey, and only go the train station once it starts to get close to your embarkation point.

For this reason, it sometimes makes sense to take the train in one direction but not the other.

Similarly, all other things being equal, a regional train route is often more reliable than a national train route. Regional routes are shorter, and thus have less opportunity to become drastically behind schedule.