Travel alerts & Trip Protection
Learn more ›

Cheap train tickets from Windsor, ON to Chicago


Schedule & Pricing Info

How much are train tickets from Windsor, ON to Chicago?

Lowest Price€30.43
Fastest Train9h 40m
Trains Per Day1
Train Lines1
Lowest PricesWe work directly with hundreds of carriers to find the best available fares.
No Wanderu FeesWe never add any extra fees. We just make it easy to book your travels.
Best Travel OptionsWe help you find & compare the best buses, trains and flights in one place.

Frequently Asked Questions

How do you find cheap train tickets from Windsor, ON to Chicago?

The most surefire way to find the lowest-priced train tickets from Windsor to Chicago is to plan ahead and book your train travel earlier. In the past 30 days, the cheapest average price users have found for trains from Windsor to Chicago was €30.43. Trying to save on a last-minute fare and have a bit of flexibility on what day to travel? Take a look at midweek schedules, as these tend to be less busy and are often cheaper than buying tickets to travel on Friday, or a weekend departure.

How long is the train ride from Windsor, ON to Chicago?

The distance between Windsor and Chicago is approximately 237.53 miles, or 382.17 kilometers. The average travel time for a train between these two cities is around 9 hours and 46 minutes, although the absolute fastest you could get there is 9 hours and 40 minutes.

Looking for ways to pass the time? Most trains are equipped with Wi-Fi, which means you can stream music, browse social media or get some work done during your ride. That said, in case your train has a spotty signal, or is among the few without Wi-Fi, we also recommend downloading TV shows and movies to your mobile device in advance of your trip. That way the ride will fly by whatever the Wi-Fi situation.

What is the busiest day for trains from Windsor to Chicago?

On Monday trains from Windsor to Chicago are the busiest. If you are looking for a great deal on your train tickets or to have extra room to stretch out, you might consider traveling on Saturday instead, as that tends to be the least traveled day of the week.

What train companies travel from Windsor to Chicago?

Typically there is one train schedule per day. One train carrier operates regular service on the Windsor to Chicago route. Amtrak offers the most scheduled departures between Windsor to Chicago, usually offering 1.188 trips per day. On this route there are no direct schedules. This means that along your journey from Windsor to Chicago, you will need to disembark from the first train and board a connecting train. Depending on the carrier's policy, you may be responsible for transferring your own checked luggage, but you will definitely need to bring your hand luggage.

One train company connects Windsor to Chicago


Amtrak train tickets from Windsor to Chicago start from €30.43, and on average cost €54.36. Daily there are 1.1875 Amtrak schedules to Chicago. Amtrak in Windsor leaves from Transit Centre, And in Chicago trains arrive at Union Station - 225 S Canal St,

From Windsor to Chicago train travel on Amtrak takes 9 hours and 46 minutes. If you are looking to get to Chicago faster, Amtrak offers more express schedule options with a travel time of 9 hours and 40 minutes.

If you're considering a weeked trip, Amtrak offers 1.428571 schedules for you to choose from. You can expect to pay €64.28 for a one-way train ticket to Chicago.

Avg. Time
9h 46m
Avg. Price

Plan your next adventure

There is one train station from which trains depart Windsor on their way to Chicago:
  • Transit Centre
There is one train station where trains from Windsor arrive in Chicago:
  • Union Station - 225 S Canal St

Book coaches, trains & flights on the go with the Wanderu app.

Download our app and snag the best travel deals across North America & Europe.Learn more

Available on iOS & Android