Next train departures

Next departures from Chicago to Waterloo on 19 August
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 20 August
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 August
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 22 August
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 August
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 August
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 August
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 26 August
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 21:38 CDT.

Compare 2 ways to travel from Chicago to Waterloo

We recommend taking the bus

Among the sustainable travel choices, the Bus stands out as a good way to reach Waterloo. The journey takes about 2 hours 45 minutes and with fares starting at just ZAR 384, it presents an excellent value for a comfortable ride.

1bus per day

2h 45mAverage duration

139 milesDistance

6kgCO₂ emissions

	Average price	Average duration	CO₂ emissions	Actions
Bus	Average priceZAR 384 - ZAR 384	Average duration2h 45m	CO₂ emissions 6kg CO₂e
Train	Average priceZAR 555 - ZAR 5,452	Average duration2h 45m	CO₂ emissions 20kg CO₂e

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

Waterloo, IN, US

A
Waterloo Station
485 W Van Vleek St, Waterloo, IN 46793, USA
Visit page

Train Companies

Amtrak

4.1/56,443 reviews

Staff4.7

Timeliness3.8

Cleanliness4.5

Wi‑Fi3.6

Based on 6443 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 ZAR 555

US train companies: Amtrak, Amtrak Acela, Brightline

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

Please note that timetables, routes, or operator details shown here may be updated or vary at the time of your journey.

How much does a train ticket cost from Chicago to Waterloo?
The cheapest train tickets from Chicago to Waterloo start from ZAR 555. The average price for this train route is around ZAR 1,021. Busbud recommends booking your tickets in advance for the best chance of getting the lowest possible price.
How long is the train journey from Chicago to Waterloo?
The average train journey time from Chicago to Waterloo is 2h 45m, covering a distance of 139 miles. The fastest train gets you there in 2h 43m and is operated by Amtrak.
Which train operators serve the Chicago to Waterloo route?
Several major train operators run on this route with 1 trains available per day.
What are the earliest and latest departure times for the train from Chicago to Waterloo?
The earliest train from Chicago to Waterloo departs at 18:40. And the latest train departs at 21:30.

Find cheapest prices for trains

Price is for a one-way ticket for one passenger and based on past searches.

Best price found

17/08

ZAR 1,183

18/08

ZAR 983

Today

ZAR 1,183

20/08

ZAR 983

21/08

ZAR 983

22/08

ZAR 983

23/08

ZAR 983

24/08

ZAR 983

The cheapest trip from Chicago to Waterloo, IN, US was searched and found on 18 Aug 2026 with a price of ZAR 983

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 ZAR 983 to ZAR 6,814 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 ZAR 983, which is on 2026-08-20.