Next train departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Train | Waterloo Station | Chicago (Union Station), IL | CheapestFastest | ||||
| Train | Waterloo Station | Chicago (Union Station), IL | No tags | ||||
| Train | Waterloo Station | Chicago (Union Station), IL | No tags | ||||
| Train | Waterloo Station | Chicago (Union Station), IL | No tags |
Last refresh of the prices: Last Monday at 8:47 PM EST.
Get from Waterloo to Chicago
The journey takes about 3 hours 9 minutes, and with fares starting at just $38, it presents an excellent value for a comfortable ride.
Train companies
Based on 5583 reviews, the company was rated 4.1 stars on Busbud. Travellers were especially satisfied with the seats and the ticket access but often complained with the WiFi. Amtrak ticket prices on this trip start at $38
Amtrak Waterloo Chicago recent customer reviews
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Where are the popular train stations and stops in Waterloo, IN, US and Chicago?
Frequently asked questions on the trip Waterloo, IN, US - Chicago
How much does a cheap train ticket from Waterloo to Chicago cost?
The average train ticket price from Waterloo to Chicago is $71. The best way to find cheap 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 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 224 km 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 include transferring trains. 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.
Find cheapest prices for trains
Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from Waterloo, IN, US to Chicago was searched and found on Nov 16, 2025 with a price of $57To 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 $57 to $583 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 $57 which is on 2025-11-16.
Top Travelled Train Routes
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