Next train departures 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 Waterloo to Chicago on 20 March Operated by Vehicle type Departure time Departure location Trip duration Arrival time Arrival location Recommended Price and booking link Train 06:36
Waterloo Station 3h 9m 08:45
Chicago (Union Station), IL Cheapest Fastest £56 Train 06:36
Waterloo Station 3h 9m 08:45
Chicago (Union Station), IL No tags £177 Train 07:51
Waterloo Station 3h 21m 10:12
Chicago (Union Station), IL No tags £177 Train 07:51
Waterloo Station 3h 21m 10:12
Chicago (Union Station), IL No tags £66
Next departures from Waterloo to Chicago on 21 March Operated by Vehicle type Departure time Departure location Trip duration Arrival time Arrival location Recommended Price and booking link Train 06:36
Waterloo Station 3h 9m 08:45
Chicago (Union Station), IL Cheapest Fastest £56 Train 06:36
Waterloo Station 3h 9m 08:45
Chicago (Union Station), IL No tags £177 Train 07:51
Waterloo Station 3h 21m 10:12
Chicago (Union Station), IL No tags £66 Train 07:51
Waterloo Station 3h 21m 10:12
Chicago (Union Station), IL No tags £223
Next departures from Waterloo to Chicago on 22 March Operated by Vehicle type Departure time Departure location Trip duration Arrival time Arrival location Recommended Price and booking link Train 06:36
Waterloo Station 3h 9m 08:45
Chicago (Union Station), IL Cheapest Fastest £47 Train 06:36
Waterloo Station 3h 9m 08:45
Chicago (Union Station), IL No tags £142 Train 07:51
Waterloo Station 3h 21m 10:12
Chicago (Union Station), IL No tags £66 Train 07:51
Waterloo Station 3h 21m 10:12
Chicago (Union Station), IL No tags £223
Next departures from Waterloo to Chicago on 23 March Operated by Vehicle type Departure time Departure location Trip duration Arrival time Arrival location Recommended Price and booking link Train 06:36
Waterloo Station 3h 9m 08:45
Chicago (Union Station), IL Cheapest Fastest £56 Train 06:36
Waterloo Station 3h 9m 08:45
Chicago (Union Station), IL No tags £142 Train 07:51
Waterloo Station 3h 21m 10:12
Chicago (Union Station), IL No tags £56 Train 07:51
Waterloo Station 3h 21m 10:12
Chicago (Union Station), IL No tags £253
Next departures from Waterloo to Chicago on 24 March Operated by Vehicle type Departure time Departure location Trip duration Arrival time Arrival location Recommended Price and booking link Train 06:36
Waterloo Station 3h 9m 08:45
Chicago (Union Station), IL Cheapest Fastest £47 Train 06:36
Waterloo Station 3h 9m 08:45
Chicago (Union Station), IL No tags £177 Train 07:51
Waterloo Station 3h 21m 10:12
Chicago (Union Station), IL No tags £56 Train 07:51
Waterloo Station 3h 21m 10:12
Chicago (Union Station), IL No tags £198
Next departures from Waterloo to Chicago on 25 March Operated by Vehicle type Departure time Departure location Trip duration Arrival time Arrival location Recommended Price and booking link Train 06:36
Waterloo Station 3h 9m 08:45
Chicago (Union Station), IL Cheapest Fastest £47 Train 06:36
Waterloo Station 3h 9m 08:45
Chicago (Union Station), IL No tags £177 Train 07:51
Waterloo Station 3h 21m 10:12
Chicago (Union Station), IL No tags £56 Train 07:51
Waterloo Station 3h 21m 10:12
Chicago (Union Station), IL No tags £488 Train 07:51
Waterloo Station 3h 21m 10:12
Chicago (Union Station), IL No tags £253
Next departures from Waterloo to Chicago on 26 March Operated by Vehicle type Departure time Departure location Trip duration Arrival time Arrival location Recommended Price and booking link Train 06:36
Waterloo Station 3h 9m 08:45
Chicago (Union Station), IL Cheapest Fastest £47 Train 06:36
Waterloo Station 3h 9m 08:45
Chicago (Union Station), IL No tags £177 Train 07:51
Waterloo Station 3h 21m 10:12
Chicago (Union Station), IL No tags £66 Train 07:51
Waterloo Station 3h 21m 10:12
Chicago (Union Station), IL No tags £177
Last refresh of the prices: Yesterday at 23:59 EDT.
View all departures Where are the popular train stations and stops in Waterloo, IN, US and Chicago? 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 Waterloo, IN, US to Chicago was searched and found on 17 Mar 2026 with a price of £43 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 £43 to £243 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 £45, which is on 2026-03-22.
Top Travelled Train Routes People from around the world trust Busbud
The cheapest trip from Waterloo, IN, US to Chicago was searched and found on 17 Mar 2026 with a price of £43
