Two Amtrak routes stop in Milwaukee, Wisconsin: Hiawatha (multiple trains each day that travel to and from Chicago) and the long-distance Empire Builder. In addition to Chicago, you can board a Milwaukee-bound train from cities in Wisconsin, Minnesota, North Dakota, Montana and Washington State (plus Portland, Oregon). If your starting location is not near one of the cities on these two routes, you’ll need to travel to Chicago first and transfer to a Hiawatha train there.
Tip: Milwaukee is an easy day trip from Chicago because of the the multiple Hiawatha trains and a trip time of only 1.5 hours.
To view all your trip options and travel times, use the “Find Trains” feature on the Amtrak.com homepage (allow a few seconds for it to load):
Amtrak Guide 