The cheapest and fastest trains from Waterloo, IN to Chicago, IL
Cheapest price
$75
Average price
$83
Fastest journey
3 h 9 m
Average duration
3 h 26 m
Trains per day
3
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 $83 if you buy it on the day, but the cheapest tickets can be found for only $75.
Of the 3 trains that leave Waterloo, IN for Chicago, IL on Mon, Dec 01, 3 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Mon, Dec 01 the direct trains cover the 223 km distance in an average of 3 h 26 m but if you time it right, some trains will get you there in just 3 h 9 m .
On Mon, Dec 01 the slowest trains will take 3 h 49 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 €22. For those with little time consider booking a flight which can get you there in 1h 14m. 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 €22, and a flight costs an average of €174.
Distance: 138 miles (223 km)
Compare train with
Most popular Train | Flight |
|---|---|
€56 Average price Cheapest | €266 Average price |
3h 48m Average total duration 3h 18m Onboard + 30m Additional time* | 4h 14m Average total duration Fastest 1h 14m 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 today, Sunday, November 30. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 10:36 AM Waterloo, IN | 3h09 | 1:45 PM Chicago, IL | 0 transfersDirect | |
![]() | 11:51 AM Waterloo, IN | 3h21 | 3:12 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.
Dec 01
Dec 02
Dec 03
Dec 04
Dec 05
Dec 06
Dec 07
Dec 08
Dec 09
Dec 10
Dec 11
Dec 12
Dec 13
Dec 14
Why should you book Waterloo to Chicago trains with Omio?
Amtrak operates all train services from Waterloo to Chicago. Omio is the only official third party seller for Amtrak tickets.
Why book with Omio vs Amtrak?
- Designed for International Travelers: Omio is in your language including 24/7 customer service and offers multiple payment options, including PayPal, credit cards, and bank transfer, in your preferred currency.
- Compare all your options: Omio allows you to compare Amtrak with all available travel options, which are train and flight to ensure you get the best deal for traveling from Waterloo to Chicago.
Why book with Omio over Trainline and Rail Europe?
- Official reseller: Amtrak tickets can only be bought on Omio or Amtrak's website as Omio is the only official third party seller for Amtrak tickets. Trainline, RailEurope, and Rail.Ninja do not sell Amtrak tickets as they are not official sellers.
- Multiple modes of transport: Omio allows you to compare travel options including train and flight to find the ideal travel option from Waterloo to Chicago.
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 18m. Cheap train tickets for this journey start at $27 (€22) 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 18m |
Cheapest ticket price $27 (€22) |
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 $27 (€22). 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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