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 R 1 247 Train 18:40
Chicago (Union Station), IL 2h 43m 22:23
Waterloo Station No tags R 4 456 Train 21:30
Chicago (Union Station), IL 2h 45m 01:15
Waterloo Station No tags R 1 247 Train 21:30
Chicago (Union Station), IL 2h 45m 01:15
Waterloo Station No tags R 5 015
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 R 1 247 Train 18:40
Chicago (Union Station), IL 2h 43m 22:23
Waterloo Station Fastest R 1 482 Train 18:40
Chicago (Union Station), IL 2h 43m 22:23
Waterloo Station No tags R 5 015 Train 21:30
Chicago (Union Station), IL 2h 45m 01:15
Waterloo Station No tags R 7 358
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 R 1 247 Train 18:40
Chicago (Union Station), IL 2h 43m 22:23
Waterloo Station Fastest R 1 482 Train 18:40
Chicago (Union Station), IL 2h 43m 22:23
Waterloo Station No tags R 7 358 Train 21:30
Chicago (Union Station), IL 2h 45m 01:15
Waterloo Station No tags R 3 555
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 R 1 482 Train 18:40
Chicago (Union Station), IL 2h 43m 22:23
Waterloo Station No tags R 3 969 Train 21:30
Chicago (Union Station), IL 2h 45m 01:15
Waterloo Station No tags R 1 482 Train 21:30
Chicago (Union Station), IL 2h 45m 01:15
Waterloo Station No tags R 5 682
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 R 1 247 Train 18:40
Chicago (Union Station), IL 2h 43m 22:23
Waterloo Station No tags R 5 015 Train 21:30
Chicago (Union Station), IL 2h 45m 01:15
Waterloo Station No tags R 1 247 Train 21:30
Chicago (Union Station), IL 2h 45m 01:15
Waterloo Station No tags R 4 456
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 R 1 049 Train 18:40
Chicago (Union Station), IL 2h 43m 22:23
Waterloo Station Fastest R 1 247 Train 18:40
Chicago (Union Station), IL 2h 43m 22:23
Waterloo Station No tags R 4 456 Train 21:30
Chicago (Union Station), IL 2h 45m 01:15
Waterloo Station No tags R 10 981 Train 21:30
Chicago (Union Station), IL 2h 45m 01:15
Waterloo Station No tags R 3 194
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 R 1 049 Train 18:40
Chicago (Union Station), IL 2h 43m 22:23
Waterloo Station No tags R 3 969 Train 21:30
Chicago (Union Station), IL 2h 45m 01:15
Waterloo Station No tags R 1 247 Train 21:30
Chicago (Union Station), IL 2h 45m 01:15
Waterloo Station No tags R 3 555
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 R 1 049 Train 18:40
Chicago (Union Station), IL 2h 43m 22:23
Waterloo Station Fastest R 1 247 Train 18:40
Chicago (Union Station), IL 2h 43m 22:23
Waterloo Station No tags R 5 682 Train 21:30
Chicago (Union Station), IL 2h 45m 01:15
Waterloo Station No tags R 3 555
Last refresh of the prices: Today at 12:00 AM 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 R 993 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 R 993 to R 10 589 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 R 993, which is on 2026-03-24.
Top Travelled Train Routes People from around the world trust Busbud
The cheapest trip from Chicago to Waterloo, IN, US was searched and found on 24 Mar 2026 with a price of R 993
