Next train departures Today, 19 Mar Tomorrow, 20 Mar Sat, 21 Mar Sun, 22 Mar Mon, 23 Mar Tue, 24 Mar Wed, 25 Mar Thu, 26 Mar More dates
Next departures from Chicago to Waterloo on 19 March Operated by Vehicle type Departure time Departure location Trip duration Arrival time Arrival location Recommended Price and booking link Train 18:40
Chicago (Union Station), IL 2h 43m 22:23
Waterloo Station Cheapest Fastest €65 Train 18:40
Chicago (Union Station), IL 2h 43m 22:23
Waterloo Station No tags €229 Train 21:30
Chicago (Union Station), IL 2h 45m 01:15
Waterloo Station No tags €65 Train 21:30
Chicago (Union Station), IL 2h 45m 01:15
Waterloo Station No tags €258
Next departures from Chicago to Waterloo on 20 March 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 Cheapest €65 Train 18:40
Chicago (Union Station), IL 2h 43m 22:23
Waterloo Station Fastest €77 Train 18:40
Chicago (Union Station), IL 2h 43m 22:23
Waterloo Station No tags €258 Train 21:30
Chicago (Union Station), IL 2h 45m 01:15
Waterloo Station No tags €379
Next departures from Chicago to Waterloo on 21 March 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 Cheapest €65 Train 18:40
Chicago (Union Station), IL 2h 43m 22:23
Waterloo Station Fastest €77 Train 18:40
Chicago (Union Station), IL 2h 43m 22:23
Waterloo Station No tags €379 Train 21:30
Chicago (Union Station), IL 2h 45m 01:15
Waterloo Station No tags €183
Next departures from Chicago to Waterloo on 22 March Operated by Vehicle type Departure time Departure location Trip duration Arrival time Arrival location Recommended Price and booking link Train 18:40
Chicago (Union Station), IL 2h 43m 22:23
Waterloo Station Cheapest Fastest €77 Train 18:40
Chicago (Union Station), IL 2h 43m 22:23
Waterloo Station No tags €204 Train 21:30
Chicago (Union Station), IL 2h 45m 01:15
Waterloo Station No tags €77 Train 21:30
Chicago (Union Station), IL 2h 45m 01:15
Waterloo Station No tags €292
Next departures from Chicago to Waterloo on 23 March Operated by Vehicle type Departure time Departure location Trip duration Arrival time Arrival location Recommended Price and booking link Train 18:40
Chicago (Union Station), IL 2h 43m 22:23
Waterloo Station Cheapest Fastest €65 Train 18:40
Chicago (Union Station), IL 2h 43m 22:23
Waterloo Station No tags €258 Train 21:30
Chicago (Union Station), IL 2h 45m 01:15
Waterloo Station No tags €65 Train 21:30
Chicago (Union Station), IL 2h 45m 01:15
Waterloo Station No tags €229
Next departures from Chicago to Waterloo on 24 March 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 Cheapest €54 Train 18:40
Chicago (Union Station), IL 2h 43m 22:23
Waterloo Station Fastest €65 Train 18:40
Chicago (Union Station), IL 2h 43m 22:23
Waterloo Station No tags €229 Train 21:30
Chicago (Union Station), IL 2h 45m 01:15
Waterloo Station No tags €565 Train 21:30
Chicago (Union Station), IL 2h 45m 01:15
Waterloo Station No tags €165
Next departures from Chicago to Waterloo on 25 March Operated by Vehicle type Departure time Departure location Trip duration Arrival time Arrival location Recommended Price and booking link Train 18:40
Chicago (Union Station), IL 2h 43m 22:23
Waterloo Station Cheapest Fastest €54 Train 18:40
Chicago (Union Station), IL 2h 43m 22:23
Waterloo Station No tags €204 Train 21:30
Chicago (Union Station), IL 2h 45m 01:15
Waterloo Station No tags €65 Train 21:30
Chicago (Union Station), IL 2h 45m 01:15
Waterloo Station No tags €183
Next departures from Chicago to Waterloo on 26 March 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 Cheapest €54 Train 18:40
Chicago (Union Station), IL 2h 43m 22:23
Waterloo Station Fastest €65 Train 18:40
Chicago (Union Station), IL 2h 43m 22:23
Waterloo Station No tags €292 Train 21:30
Chicago (Union Station), IL 2h 45m 01:15
Waterloo Station No tags €183
Last refresh of the prices: Today at 00:00 CDT.
View all departures Where are the popular train stations and stops in Chicago and Waterloo, IN, US? Chicago A
Union Station
225 S Canal St, Chicago, IL 60606, USA Map
Find cheapest prices for trains Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from Chicago to Waterloo, IN, US was searched and found on 24 Mar 2026 with a price of €52 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 €52 to €545 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 €52, which is on 2026-03-24.
Top Travelled Train Routes People from around the world trust Busbud
Popular train departures from Chicago Popular train routes to Waterloo Continue your journey from Waterloo 
The cheapest trip from Chicago to Waterloo, IN, US was searched and found on 24 Mar 2026 with a price of €52
