Travel By Train to Chicago

  James  3 mins read.

Travel By Train

If you live anywhere in the Midwest taking a train to Chicago can be 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 intermittent, yet is generally sufficient for emailing and basic web browsing.

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

Consider a Roomette


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 ADA accessible than the lower levels.

Avoid Connections

Going across the country on Amtrak works best if you are able to avoid any connections aside from those with frequent commuter lines.

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.

  • 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).

Summary of Mid-West Train Options To Chicago

Train Schedule Reliability

In my experience, the schedule reliability of a long-distance Amtrak train becomes increasingly worse the further 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 check the train status during its journey, and only go to the train station once the train 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.

Consider checking historical arrival and departure times before you finalize your travel plans.