Amtrak Milwaukee to Chicago: Cost, Comfort, and Booking Tips Amtrak Milwaukee to Chicago is a popular rail route offering a fast, comfortable, and affordable way to travel between the two cities. Ticket prices typically start at around $19 when booked early, but fares may increase closer to the travel date. To find the cheapest fares for <a href="https://www.zadrails.com/blog/how-to-travel-from-milwaukee-to-chicago-by-amtrak/ ">**amtrak milwaukee to chicago**</a>, book in advance, travel during weekdays or off-peak hours, and look for available discounts. Checking Amtrak’s website regularly for promotions can also help travelers save money on their journey.