Next train departures

Next departures from Chicago to Waterloo on 8 October
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wi‑Fi Toilet Power outlets	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	Cheapest
Train Wi‑Fi Toilet Power outlets	18:40	Chicago (Union Station), IL	2h 43m	22:23	Waterloo Station	Fastest
Train Wi‑Fi Toilet Power outlets	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	No tags

Next departures from Chicago to Waterloo on 9 October
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wi‑Fi Toilet Power outlets	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	Cheapest
Train Wi‑Fi Toilet Power outlets	18:40	Chicago (Union Station), IL	2h 43m	22:23	Waterloo Station	Fastest
Train Wi‑Fi Toilet Power outlets	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	No tags

Next departures from Chicago to Waterloo on 10 October
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wi‑Fi Toilet Power outlets	18:40	Chicago (Union Station), IL	2h 43m	22:23	Waterloo Station	CheapestFastest
Train Wi‑Fi Toilet Power outlets	18:40	Chicago (Union Station), IL	2h 43m	22:23	Waterloo Station	No tags
Train Wi‑Fi Toilet Power outlets	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	No tags
Train Wi‑Fi Toilet Power outlets	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	No tags

Next departures from Chicago to Waterloo on 11 October
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wi‑Fi Toilet Power outlets	17:35	Chicago (Union Station), IL	2h 43m	21:18	Waterloo Station	CheapestFastest
Train Wi‑Fi Toilet Power outlets	17:35	Chicago (Union Station), IL	2h 43m	21:18	Waterloo Station	No tags
Train Wi‑Fi Toilet Power outlets	20:30	Chicago (Union Station), IL	2h 45m	00:15	Waterloo Station	No tags

Next departures from Chicago to Waterloo on 12 October
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wi‑Fi Toilet Power outlets	18:40	Chicago (Union Station), IL	2h 43m	22:23	Waterloo Station	CheapestFastest
Train Wi‑Fi Toilet Power outlets	18:40	Chicago (Union Station), IL	2h 43m	22:23	Waterloo Station	No tags
Train Wi‑Fi Toilet Power outlets	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	No tags
Train Wi‑Fi Toilet Power outlets	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	No tags

Next departures from Chicago to Waterloo on 13 October
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wi‑Fi Toilet Power outlets	18:40	Chicago (Union Station), IL	2h 43m	22:23	Waterloo Station	CheapestFastest
Train Wi‑Fi Toilet Power outlets	18:40	Chicago (Union Station), IL	2h 43m	22:23	Waterloo Station	No tags
Train Wi‑Fi Toilet Power outlets	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	No tags
Train Wi‑Fi Toilet Power outlets	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	No tags
Train Wi‑Fi Toilet Power outlets	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	No tags

Next departures from Chicago to Waterloo on 14 October
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wi‑Fi Toilet Power outlets	18:40	Chicago (Union Station), IL	2h 43m	22:23	Waterloo Station	CheapestFastest
Train Wi‑Fi Toilet Power outlets	18:40	Chicago (Union Station), IL	2h 43m	22:23	Waterloo Station	No tags
Train Wi‑Fi Toilet Power outlets	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	No tags
Train Wi‑Fi Toilet Power outlets	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	No tags
Train Wi‑Fi Toilet Power outlets	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	No tags

Next departures from Chicago to Waterloo on 15 October
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train Wi‑Fi Toilet Power outlets	18:40	Chicago (Union Station), IL	2h 43m	22:23	Waterloo Station	CheapestFastest
Train Wi‑Fi Toilet Power outlets	18:40	Chicago (Union Station), IL	2h 43m	22:23	Waterloo Station	No tags
Train Wi‑Fi Toilet Power outlets	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	No tags
Train Wi‑Fi Toilet Power outlets	21:30	Chicago (Union Station), IL	2h 45m	01:15	Waterloo Station	No tags

Last refresh of the prices: Yesterday at 23:09 CDT.

Compare 2 ways to travel from Chicago to Waterloo

We recommend taking the train

Among the sustainable travel choices, the Train stands out as a good way to reach Waterloo. The journey takes about 2 hours 43 minutes and with fares starting at just SGD 46, it presents an excellent value for a comfortable ride.

2train per day

2h 43mAverage duration

139 milesDistance

20kgCO₂ emissions

	Average price	Average duration	CO₂ emissions	Actions
Bus	Average priceSGD 31 - SGD 31	Average duration2h 45m	CO₂ emissions 6kg CO₂e
Train	Average priceSGD 46 - SGD 118	Average duration2h 43m	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
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Train Companies

Amtrak

4.1/56,556 reviews

Staff4.7

Timeliness3.8

Cleanliness4.5

Wi‑Fi3.6

Based on 6556 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 SGD 46

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 SGD 46. The average price for this train route is around SGD 70. 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 43m, 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 2 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

06/10

SGD 78

07/10

SGD 78

Today

SGD 78

09/10

SGD 78

10/10

SGD 66

11/10

SGD 94

12/10

SGD 78

13/10

SGD 66

The cheapest trip from Chicago to Waterloo, IN, US was searched and found on 10 Oct 2026 with a price of SGD 66

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 SGD 66 to SGD 700 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 SGD 66, which is on 2026-10-10.