Next train departures

Next departures from Waterloo to Chicago on 24 September
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wi‑Fi Toilet Power outlets	06:36	Waterloo Station	3h 9m	08:45	Chicago (Union Station), IL	CheapestFastest
Train Wi‑Fi Toilet Power outlets	06:36	Waterloo Station	3h 9m	08:45	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	07:51	Waterloo Station	3h 21m	10:12	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	07:51	Waterloo Station	3h 21m	10:12	Chicago (Union Station), IL	No tags

Next departures from Waterloo to Chicago on 25 September
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wi‑Fi Toilet Power outlets	06:36	Waterloo Station	3h 9m	08:45	Chicago (Union Station), IL	CheapestFastest
Train Wi‑Fi Toilet Power outlets	06:36	Waterloo Station	3h 9m	08:45	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	07:51	Waterloo Station	3h 21m	10:12	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	07:51	Waterloo Station	3h 21m	10:12	Chicago (Union Station), IL	No tags

Next departures from Waterloo to Chicago on 26 September
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wi‑Fi Toilet Power outlets	06:36	Waterloo Station	3h 9m	08:45	Chicago (Union Station), IL	CheapestFastest
Train Wi‑Fi Toilet Power outlets	06:36	Waterloo Station	3h 9m	08:45	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	07:51	Waterloo Station	3h 21m	10:12	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	07:51	Waterloo Station	3h 21m	10:12	Chicago (Union Station), IL	No tags

Next departures from Waterloo to Chicago on 27 September
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wi‑Fi Toilet Power outlets	06:36	Waterloo Station	3h 9m	08:45	Chicago (Union Station), IL	CheapestFastest
Train Wi‑Fi Toilet Power outlets	06:36	Waterloo Station	3h 9m	08:45	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	07:51	Waterloo Station	3h 21m	10:12	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	07:51	Waterloo Station	3h 21m	10:12	Chicago (Union Station), IL	No tags

Next departures from Waterloo to Chicago on 28 September
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wi‑Fi Toilet Power outlets	06:36	Waterloo Station	3h 9m	08:45	Chicago (Union Station), IL	CheapestFastest
Train Wi‑Fi Toilet Power outlets	06:36	Waterloo Station	3h 9m	08:45	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	07:51	Waterloo Station	3h 21m	10:12	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	07:51	Waterloo Station	3h 21m	10:12	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	07:51	Waterloo Station	3h 21m	10:12	Chicago (Union Station), IL	No tags

Next departures from Waterloo to Chicago on 29 September
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wi‑Fi Toilet Power outlets	06:36	Waterloo Station	3h 9m	08:45	Chicago (Union Station), IL	CheapestFastest
Train Wi‑Fi Toilet Power outlets	06:36	Waterloo Station	3h 9m	08:45	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	07:51	Waterloo Station	3h 21m	10:12	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	07:51	Waterloo Station	3h 21m	10:12	Chicago (Union Station), IL	No tags

Next departures from Waterloo to Chicago on 30 September
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wi‑Fi Toilet Power outlets	06:36	Waterloo Station	3h 9m	08:45	Chicago (Union Station), IL	CheapestFastest
Train Wi‑Fi Toilet Power outlets	06:36	Waterloo Station	3h 9m	08:45	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	07:51	Waterloo Station	3h 21m	10:12	Chicago (Union Station), IL	No tags
Train Wi‑Fi Toilet Power outlets	07:51	Waterloo Station	3h 21m	10:12	Chicago (Union Station), IL	No tags

Last refresh of the prices: Last Monday at 21:44 EDT.

Compare 2 ways to travel from Waterloo to Chicago

We recommend taking the bus

Among the sustainable travel choices, the Bus stands out as a good way to reach Chicago. The journey takes about 3 hours 9 minutes and with fares starting at just PEN 80, it presents an excellent value for a comfortable ride.

2bus per day

3h 9mAverage duration

139 milesDistance

6kgCO₂ emissions

	Average price	Average duration	CO₂ emissions	Actions
Bus	Average pricePEN 80 - PEN 80	Average duration3h 9m	CO₂ emissions 6kg CO₂e
Train	Average pricePEN 119 - PEN 309	Average duration3h 9m	CO₂ emissions 20kg CO₂e

Where are the popular train stations and stops in Waterloo, IN, US and Chicago?

Waterloo, IN, US

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

Chicago

A
Union Station
225 S Canal St, Chicago, IL 60606, USA

Train Companies

Amtrak

4.1/56,503 reviews

Staff4.7

Timeliness3.8

Cleanliness4.5

Wi‑Fi3.6

Based on 6503 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 PEN 119

Amtrak Waterloo Chicago recent customer reviews

Nice people

J Lorenzo L.

16 February 2024

US train companies: Amtrak, Amtrak Acela, Brightline

Frequently asked questions about travelling from Waterloo, IN, US to Chicago 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 Waterloo to Chicago?
The cheapest train tickets from Waterloo to Chicago start from PEN 119. The average price for this train route is around PEN 184. Busbud recommends booking your tickets in advance for the best chance of getting the lowest possible price.
How long is the train journey from Waterloo to Chicago?
The average train journey time from Waterloo to Chicago is 3h 9m, covering a distance of 139 miles. The fastest train gets you there in 3h 9m and is operated by Amtrak.
Which train operators serve the Waterloo to Chicago route?
Several major train operators run on this route with 2 trains available per day.
What are the earliest and latest departure times for the train from Waterloo to Chicago?
The earliest train from Waterloo to Chicago departs at 06:36. And the latest train departs at 07:51.

Find cheapest prices for trains

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

Best price found

21/09

PEN 173

22/09

PEN 173

Today

PEN 149

24/09

PEN 173

25/09

PEN 173

26/09

PEN 173

27/09

PEN 149

28/09

PEN 173

The cheapest trip from Waterloo, IN, US to Chicago was searched and found on 23 Sept 2026 with a price of PEN 149

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 PEN 149 to PEN 1,845 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 PEN 149, which is on 2026-09-27.