Next train departures Tomorrow, Mar 20 Sat, Mar 21 Sun, Mar 22 Mon, Mar 23 Tue, Mar 24 Wed, Mar 25 Thu, Mar 26 More dates
Next departures for Waterloo to Chicago on March 20 Operated by Vehicle type Departure time Departure location Trip duration Arrival time Arrival location Recommended Price and booking link Train 6:36am
Waterloo Station 3h 9m 8:45am
Chicago (Union Station), IL Cheapest Fastest $72 Train 6:36am
Waterloo Station 3h 9m 8:45am
Chicago (Union Station), IL No tags $228 Train 7:51am
Waterloo Station 3h 21m 10:12am
Chicago (Union Station), IL No tags $228 Train 7:51am
Waterloo Station 3h 21m 10:12am
Chicago (Union Station), IL No tags $86
Next departures for Waterloo to Chicago on March 21 Operated by Vehicle type Departure time Departure location Trip duration Arrival time Arrival location Recommended Price and booking link Train 6:36am
Waterloo Station 3h 9m 8:45am
Chicago (Union Station), IL Cheapest Fastest $72 Train 6:36am
Waterloo Station 3h 9m 8:45am
Chicago (Union Station), IL No tags $228 Train 7:51am
Waterloo Station 3h 21m 10:12am
Chicago (Union Station), IL No tags $86 Train 7:51am
Waterloo Station 3h 21m 10:12am
Chicago (Union Station), IL No tags $288
Next departures for Waterloo to Chicago on March 22 Operated by Vehicle type Departure time Departure location Trip duration Arrival time Arrival location Recommended Price and booking link Train 6:36am
Waterloo Station 3h 9m 8:45am
Chicago (Union Station), IL Cheapest Fastest $61 Train 6:36am
Waterloo Station 3h 9m 8:45am
Chicago (Union Station), IL No tags $184 Train 7:51am
Waterloo Station 3h 21m 10:12am
Chicago (Union Station), IL No tags $86 Train 7:51am
Waterloo Station 3h 21m 10:12am
Chicago (Union Station), IL No tags $288
Next departures for Waterloo to Chicago on March 23 Operated by Vehicle type Departure time Departure location Trip duration Arrival time Arrival location Recommended Price and booking link Train 6:36am
Waterloo Station 3h 9m 8:45am
Chicago (Union Station), IL Cheapest Fastest $72 Train 6:36am
Waterloo Station 3h 9m 8:45am
Chicago (Union Station), IL No tags $184 Train 7:51am
Waterloo Station 3h 21m 10:12am
Chicago (Union Station), IL No tags $72 Train 7:51am
Waterloo Station 3h 21m 10:12am
Chicago (Union Station), IL No tags $327
Next departures for Waterloo to Chicago on March 24 Operated by Vehicle type Departure time Departure location Trip duration Arrival time Arrival location Recommended Price and booking link Train 6:36am
Waterloo Station 3h 9m 8:45am
Chicago (Union Station), IL Cheapest Fastest $61 Train 6:36am
Waterloo Station 3h 9m 8:45am
Chicago (Union Station), IL No tags $228 Train 7:51am
Waterloo Station 3h 21m 10:12am
Chicago (Union Station), IL No tags $72 Train 7:51am
Waterloo Station 3h 21m 10:12am
Chicago (Union Station), IL No tags $256
Next departures for Waterloo to Chicago on March 25 Operated by Vehicle type Departure time Departure location Trip duration Arrival time Arrival location Recommended Price and booking link Train 6:36am
Waterloo Station 3h 9m 8:45am
Chicago (Union Station), IL Cheapest Fastest $61 Train 6:36am
Waterloo Station 3h 9m 8:45am
Chicago (Union Station), IL No tags $228 Train 7:51am
Waterloo Station 3h 21m 10:12am
Chicago (Union Station), IL No tags $72 Train 7:51am
Waterloo Station 3h 21m 10:12am
Chicago (Union Station), IL No tags $631 Train 7:51am
Waterloo Station 3h 21m 10:12am
Chicago (Union Station), IL No tags $327
Next departures for Waterloo to Chicago on March 26 Operated by Vehicle type Departure time Departure location Trip duration Arrival time Arrival location Recommended Price and booking link Train 6:36am
Waterloo Station 3h 9m 8:45am
Chicago (Union Station), IL Cheapest Fastest $61 Train 6:36am
Waterloo Station 3h 9m 8:45am
Chicago (Union Station), IL No tags $228 Train 7:51am
Waterloo Station 3h 21m 10:12am
Chicago (Union Station), IL No tags $86 Train 7:51am
Waterloo Station 3h 21m 10:12am
Chicago (Union Station), IL No tags $228
Last refresh of the prices: Yesterday at 11:59 PM 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 Mar 17, 2026 with a price of $55 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 $55 to $314 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 2026-03-22.
Top Traveled Train Routes People from around the world trust Busbud
Popular train departures from Waterloo Popular train routes to Chicago Continue your journey from Chicago 
The cheapest trip from Waterloo, IN, US to Chicago was searched and found on Mar 17, 2026 with a price of $55
