How much does a cheap train ticket from Chicago to Waterloo cost?

The average train ticket price from Chicago to Waterloo is £33. The best way to find cheap train tickets from Chicago to Waterloo 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 Chicago to Waterloo?

A train trip between Chicago and Waterloo is around 2h 43m, although the fastest train will take about 2h 43m. This is the time it takes to travel the 139 miles that separates the two cities.

How many daily train are there between Chicago and Waterloo?

The number of trains from Chicago to Waterloo 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 Chicago to Waterloo by comparing and selecting the train that fits your travel style and budget on Busbud.

Which train companies travel from Chicago to Waterloo?

When taking the train from Chicago to Waterloo, you can travel comfortably and safely with Amtrak.

Train Chicago to Waterloo from £19 | Refundable Tickets

Next train departures

Next departures from Chicago to Waterloo on 18 November
Operated by	Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended	Price and booking link
	Train	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	CheapestFastest
	Train	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	No tags

Next departures from Chicago to Waterloo on 19 November
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	Cheapest
Train	18:40	Chicago (Union Station), IL	2h 43m	22:23	Waterloo Station	Fastest
Train	18:40	Chicago (Union Station), IL	2h 43m	22:23	Waterloo Station	No tags
Train	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	No tags

Next departures from Chicago to Waterloo on 20 November
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	Cheapest
Train	18:40	Chicago (Union Station), IL	2h 43m	22:23	Waterloo Station	Fastest
Train	18:40	Chicago (Union Station), IL	2h 43m	22:23	Waterloo Station	No tags
Train	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	No tags

Next departures from Chicago to Waterloo on 21 November
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	18:40	Chicago (Union Station), IL	2h 43m	22:23	Waterloo Station	CheapestFastest
Train	18:40	Chicago (Union Station), IL	2h 43m	22:23	Waterloo Station	No tags
Train	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	No tags
Train	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	No tags

Next departures from Chicago to Waterloo on 22 November
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	Cheapest
Train	18:40	Chicago (Union Station), IL	2h 43m	22:23	Waterloo Station	Fastest
Train	18:40	Chicago (Union Station), IL	2h 43m	22:23	Waterloo Station	No tags
Train	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	No tags

Next departures from Chicago to Waterloo on 23 November
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	Cheapest
Train	18:40	Chicago (Union Station), IL	2h 43m	22:23	Waterloo Station	Fastest
Train	18:40	Chicago (Union Station), IL	2h 43m	22:23	Waterloo Station	No tags
Train	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	No tags

Next departures from Chicago to Waterloo on 24 November
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	Cheapest
Train	18:40	Chicago (Union Station), IL	2h 43m	22:23	Waterloo Station	Fastest
Train	18:40	Chicago (Union Station), IL	2h 43m	22:23	Waterloo Station	No tags
Train	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	No tags

Next departures from Chicago to Waterloo on 25 November
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	18:40	Chicago (Union Station), IL	2h 43m	22:23	Waterloo Station	CheapestFastest
Train	18:40	Chicago (Union Station), IL	2h 43m	22:23	Waterloo Station	No tags
Train	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	No tags
Train	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	No tags

Last refresh of the prices: Yesterday at 21:48 CST.

Get from Chicago to Waterloo

This route is served by train only

The journey takes about 2 hours 43 minutes, and with fares starting at just £21, it presents an excellent value for a comfortable ride.

2train per day

2h 43mAverage duration

139 milesDistance

20kgCO₂ emissions

Train Companies

Amtrak

4/55,593 reviews

Staff4.7

Timeliness3.8

Cleanliness4.6

WiFi3.6

Based on 5593 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 Wi-Fi. Amtrak ticket prices on this trip start at £21

US train companies: Amtrak, Trenitalia, Renfe, VIA Rail Canada, Amtrak Acela, NS Nederlandse Spoorwegen, Iryo

Where are the popular train stations and stops in Chicago and Waterloo, IN, US?

Stops in Chicago

A - Union Station

Stops in Waterloo, IN, US

A - Waterloo Station

Frequently asked questions about travelling from Chicago to Waterloo, IN, US by train

How much does a cheap train ticket from Chicago to Waterloo cost?
The average train ticket price from Chicago to Waterloo is £33. The best way to find cheap train tickets from Chicago to Waterloo 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 Chicago to Waterloo?
A train trip between Chicago and Waterloo is around 2h 43m, although the fastest train will take about 2h 43m. This is the time it takes to travel the 139 miles that separates the two cities.
How many daily train are there between Chicago and Waterloo?
The number of trains from Chicago to Waterloo 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 Chicago to Waterloo by comparing and selecting the train that fits your travel style and budget on Busbud.
Which train companies travel from Chicago to Waterloo?
When taking the train from Chicago to Waterloo, 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.

Best price found

16/11

£36

17/11

£36

Today

£31

19/11

£31

20/11

£36

21/11

£62

22/11

£52

23/11

£52

The cheapest trip from Chicago to Waterloo, IN, US was searched and found on 18 Nov 2025 with a price of £31

To save money and be sure you have the best seat, it's a good idea to buy your train tickets from Chicago to Waterloo, IN, US as early as possible.

You can expect to pay from £31 to £360 for a train ticket from Chicago to Waterloo, IN, US based on the last 2 days. You can expect to find the cheapest price for the trip at £31, which is on 2025-11-19.