Based on 5583 reviews, the company was rated 4.1 stars on Busbud. Travelers were especially satisfied with the seats and the ticket access but often complained with the wifi. Amtrak ticket prices on this trip start at $27
Frequently asked questions for your trip Waterloo, IN, US - Chicago
How much does a train ticket from Waterloo to Chicago cost?
The average train ticket price from Waterloo to Chicago is $49. The best way to find train tickets from Waterloo to Chicago is to book your tickets as early as possible. Prices tend to rise as your travel date approaches, so book in advance to secure the best prices!
How long is the train trip from Waterloo to Chicago?
A train trip between Waterloo and Chicago is around 3h 9m, although the fastest train will take about 3h 9m. This is the time it takes to travel the 139 miles that separates the two cities.
How many daily trains are there between Waterloo and Chicago?
The number of trains from Waterloo to Chicago can differ depending on the day of the week. On average, there are 2. Some trains are direct while others have layovers. Simplify your train trip from Waterloo to Chicago by comparing and selecting the train that fits your travel style and budget on Busbud.
Which train companies travel from Waterloo to Chicago?
When taking the train from Waterloo to Chicago, you can travel comfortably and safely with Amtrak.
What are the best sights and things to do in Chicago?
Once in Chicago, you can explore the city. The top sights and things to do are Museum of Contemporary Art, Willis Tower (Sears Tower), Chicago Shakespeare Theater on Navy Pier, Navy Pier, Lincoln Park Zoo.
Find cheapest prices for trains
Price is for a one-way ticket for one passenger and based on past searches.
Best price found
11/11
$66
11/12
$55
Today
$66
11/14
$66
11/15
$55
11/16
$39
11/17
$46
11/18
$46
The cheapest trip from Waterloo, IN, US to Chicago was searched and found on Nov 16, 2025 with a price of $39
To save money and be sure you have the best seat, it's a good idea to buy your train tickets from Waterloo, IN, US to Chicago, as early as possible.
You can expect to pay from $39 to $405 for a train ticket from Waterloo, IN, US to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at $39 which is on 2025-11-16.
The cheapest trip from Waterloo, IN, US to Chicago was searched and found on Nov 16, 2025 with a price of $39
