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San Jose-Chicago Train Schedule

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Trip Summary

There are 5 daily trains from San Jose to Chicago. Traveling by train from San Jose to Chicago usually takes around 63 hours and 17 minutes, but the fastest Amtrak train can make the trip in 54 hours and 32 minutes.

Distance1838 mi (2958 km)
Fastest train54h 32m
Lowest price$181.61
Most frequent serviceAmtrak
Train lines1

What is the price of a train ticket from San Jose to Chicago?

In the last month, C$228.31 was the average price of a train ticket from San Jose, CA to Chicago, IL. Tickets are generally somewhat expensive for this particular train route, which is to be expected given the long distance. You can expect to find tickets at that price or lower if you book your trip at least 27 days in advance. Otherwise, expect to pay around C$121.15 more than that for a same-day booking.

Monthly average prices

$335$268$201$134$67JJASONDJFMAM

If you are trying to decide when to travel from San Jose to Chicago by train so you can score the best possible deal, your best bet would be to plan your trip for September. That’s when the average price for a train ticket is expected to be just C$232 – the lowest of the year.

Alternatively, if you plan to travel from San Jose to Chicago in December, expect to spend more on your train trip, as the average ticket price usually surges to C$312 at that time of year. However, if you book your trip ahead of time, you have a high chance of scoring a ticket at a lower price.

Prices as travel date approaches

$365$292$219$146$733020100

If you want to score the best deal, you should plan to book your train trip online on Wanderu at least 27 days ahead of time. If you do that, your train ticket to Chicago from San Jose will be about C$121.15 cheaper compared to what you would pay if you book at the last minute.

Which train should you take from San Jose to Chicago?

Amtrak is the one and only train line which connects San Jose, California to Chicago, Illinois. However, there are 5 trains per day to choose from.

TrainDaily TripsAvg. TimeAvg. Price
Amtrak52d 15h 17m$254.24
  • Amtrak

    Amtrak

    Amtrak is the largest passenger railroad service in America, offering daily intercity trains to hundreds of destinations across the contiguous United States, as well as several cities in Canada. Every Amtrak train comes equipped with comfortable seats with extra legroom, as well as several four-seat areas with tables in the middle. In addition, each car has a freshly cleaned restroom, free WiFi and power outlets at every seat. There are also snack bars where you can purchase drinks or food during your journey. On average, there are 5 Amtrak trains from San Jose to Chicago every day, as well as 5 trips on the weekends, with prices starting from $182.

    amtrak trainamtrak trainamtrak trainamtrak diningamtrak diningamtrak bathroomamtrak power outletamtrak seatamtrak seatamtrak viewliner

Frequently Asked Questions

Is it safe to travel by train from San Jose to Chicago during the COVID-19 pandemic?

Our train partners have implemented several different policies to keep you safe during the COVID-19 pandemic. From limiting vehicle capacity to enhancing cleaning protocols and upgrading air filters, train carriers are committed to maintaining a safe environment. For details on what each company is doing to ensure their fleet remains safe for travel, click here.

In addition, federal law requires all train passengers to wear a face covering for the entire duration of the trip. Please make sure you are wearing a face mask or you may not be allowed to board the train.

Please visit our COVID-19 Travel Guide for more information on all carrier policies and the latest travel advisories issued by every U.S. state, Canadian province, and European country.

Can you take a train all the way from San Jose to Chicago?

Yes, there are trains that can take you the entire way from San Jose to Chicago. However, there are also some trips on this route that require you to board another vehicle, such as a bus or a shuttle, during your journey. This is worth paying attention to as you book your trip, since a direct train may be preferable for its speed and convenience.

How long is the train journey from San Jose to Chicago?

The distance between San Jose and Chicago is approximately 1838 miles, or 2958 kilometers. The average train journey between these two cities takes 63 hours and 17 minutes, although the absolute fastest you could get there is 54 hours and 32 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.

When are trains the most crowded?

Trains from San Jose to Chicago are the most crowded on Friday. Tickets also tend to be more expensive then. If you are looking for a great deal on your train tickets or just want extra room to stretch out, consider traveling on Tuesday instead, as it tends to be the least crowded day of the week.

When are the first and last trains of the day?

The earliest train departs San Jose at 4:00am while the last train of the day leaves at 8:00pm. To see all scheduled departure times, use the search function on this page to get the full schedule for your specific travel dates.

Is there a direct train from San Jose to Chicago?

There are 5 scheduled trains on most days. Unfortunately, none of them are direct connections, so you will need to disembark from your original train and board a connecting train during your journey. Don't forget to bring your carry-on luggage when you switch trains. In some instances, you may also be responsible for transferring your own checked baggage.

You can also take a train for your return trip from Chicago to San Jose. If you're not not set on traveling by train, you could always take the bus from San Jose to Chicago for $264.06.

City Information

Chicago

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Known for its innovative architecture, cultural contributions to jazz and house music, and of course that irresistible deep-dish pizza, the many sights and experiences in Chicago make it one of the best urban vacation destinations for millennials.

You can't beat the views of the city and Lake Michigan from the SkyDeck in the Willis Tower; at over 1,300 feet, this is the highest observation deck in the U.S. Snap that classic selfie with the Bean in Millennium Park, then wander the many museums in nearby Grant Park. Navy Pier is a popular tourist hotspot for its parks, restaurants, and attractions right on Lake Michigan, and baseball fans will find paradise in Wrigleyville, home to the Chicago Cubs' Wrigley Field and sports bars galore.

Chicago's enormous parks offer plentiful opportunities for outdoor activities in gorgeous urban settings. Many companies offer kayak rentals or boat tours on the Chicago River, with special tours running on Saint Patrick's Day, when the entire river is dyed green. When you’re ready to buy some souvenirs from your epic trip, hit the big brand stores on the Magnificent Mile, or shop local in neighborhoods like Andersonville and Wicker Park. And don't miss the chance to laugh until you cry at The Second City comedy theater, famous for launching the careers of comedians like Tina Fey and Stephen Colbert.

Chicago is one of the biggest transportation hubs in the Midwest, and provides easy access to nearby destinations ideal for day trips, as well as international travel from two airports. Thanks to plenty of bus and train stations throughout the city, getting to the Windy City is a breeze.

Station Information

Where is the train station in San Jose?

Departure stations

There is one train station in San Jose:

Other train stations in San Jose:

  • Diridon Caltrain Station - 65 Cahill St

Where is the train station in Chicago?

chicago union station

Image credit: Jeramey Jannene

Link to Creative Commons License

Arrival stations

The historic Chicago Union Station is the United States' third busiest train station and a hub for 15 Amtrak train lines with destinations throughout the country. The station also serves bus carriers like Greyhound, Indian Trails and Jefferson Lines, and offers connections to Metra commuter lines. Union Station is also just a quick walk to the nearest Chicago L lines. The current station was built in 1925, to replace the original one dating back to 1881, and today wows visitors with its impressive facade, massive columns, and opulent Great Hall. Located right in downtown and adjacent to the Chicago Loop, Union Station is equipped with many services and amenities, including phone charging stations, shops, and various food and drink options.

Other train stations in Chicago:

  • Union Station - 225 S Canal St

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