The cheapest and fastest trains from Waterloo, IN to Chicago, IL
Cheapest price
$44
Average price
$45
Fastest journey
3 h 9 m
Average duration
3 h 15 m
Trains per day
2
Distance
223 km
The best way to find a cheap train ticket from Waterloo, IN to Chicago, IL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Waterloo, IN to Chicago, IL will cost around $45 if you buy it on the day, but the cheapest tickets can be found for only $44.
Of the 2 trains that leave Waterloo, IN for Chicago, IL on Sun, Mar 01, 2 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Sun, Mar 01 the direct trains cover the 223 km distance in an average of 3 h 15 m but if you time it right, some trains will get you there in just 3 h 9 m .
On Sun, Mar 01 the slowest trains will take 3 h 21 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.




Travel Information
Compare train and flight for Waterloo, IN to Chicago, IL
Omio recommends booking the train as it is the most popular option from Waterloo, IN to Chicago, IL among Omio's users. If you are prioritising price take the train with prices starting from $37. For those with little time consider booking a flight which can get you there in 1h 22m. In case you are seeking to minimise your carbon footprint the train is your best bet as it emits only 0.1 - 0.2kg. The ticket price range depends on the travel mode: a train costs an average of $37, and a flight costs an average of $180.
Distance: 138 miles (223 km)
Compare train with
Most popular Train | Flight |
|---|---|
$58 Average price Cheapest | $323 Average price |
3h 47m Average total duration 3h 17m Onboard + 30m Additional time* | 4h 22m Average total duration Fastest 1h 22m Onboard + 3h 0m Additional time* |
0.1 - 0.2kg CO2 emissions Lowest | 0.7 - 1.3kg CO2 emissions |
Direct Options | Direct Options |
Additional time: Average total travel duration to departure point, security checks and transfers.
Live departures
Waterloo, IN to Chicago, IL train times
The table below shows live departures for Waterloo, IN to Chicago, IL trains for tomorrow, Sunday, March 1. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 11:36 AM Waterloo, IN | 3h09 | 2:45 PM Chicago, IL | 0 transfersDirect | |
![]() | 12:51 PM Waterloo, IN | 3h21 | 4:12 PM Chicago, IL | 0 transfersDirect | |
This is the last train of the day. | |||||
Find all the dates and times for this journey
Compare prices and tickets Waterloo, IN to Chicago, IL by train or flight
Compare train and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
Mar 01
Mar 02
Mar 03
Mar 04
Mar 05
Mar 06
Mar 07
How far in advance should I book train tickets from Waterloo, IN to Chicago, IL?
Journey information
Overview: Train from Waterloo, IN to Chicago, IL
Trains from Waterloo, IN to Chicago, IL run on average 3 times per day, taking around 3h 17m. Cheap train tickets for this journey start at $37 (€30) if you book in advance.
There are 3 trains per day. The earliest train runs at 06:36, the last at 21:30. The fastest train covers the 138 miles (223 km) distance in 3h 9m.
Distance 138 miles (223 km) |
Average train duration 3h 17m |
Cheapest ticket price $37 (€30) |
Trains per day 3 |
Direct trains 3 |
Fastest train 3h 9m |
First train 06:36 |
Last train 21:30 |
Train companies: Amtrak from Waterloo, IN to Chicago, IL trainsAmtrak trains will get you between Waterloo, IN and Chicago, IL from $37 (€30). With over 1000 travel companies on Omio, you can find the best train times and tickets for your trip.
Amtrak
FAQs: Trains from Waterloo, IN to Chicago, IL
Find answers to the most common questions about traveling from Waterloo, IN to Chicago, IL by train. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest train, the cheapest option, or tips for making the most of your visit at Chicago, IL, this guide helps you travel smarter and with confidence.

popular train stations
Popular train stations from Waterloo, IN to Chicago, IL
- Parking is available at the station.
- Outside the station.
- Ramps.
- Free
- The station consists of a single platform with no additional halls or sections.
- Bus: No direct public transport connections
- Taxi services may be available.
- 5:00 AM - 12:00 AM Monday - Sunday
- Free
- The car park is open 7 days a week from 5:00 a.m. to 12:00 a.m. Departures can be made outside of opening hours. Access via Canal Street.
- The Chicago Firehouse Restaurant
- Lou Mitchell's
- Outside the main entrance.
- Elevators, ramps, restrooms.
- $1
- The Kimpton Gray Hotel
- JW Marriott Chicago
- W Chicago - City Center
- Located in the main hall
- Located in the main hall
- Avis
- Budget
- Enterprise
- Located in the main hall
- Free
- Hall 1: main entrance, Amtrak services
- Hall 2: Metra services
- Hall 3: food court and retail shops
- Bus: Several lines available
- CTA: Blue Line, Pink Line
More options for your journey from Waterloo, IN to Chicago, IL
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