Cheap train tickets from Chicago to San Jose

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Trip Summary

There are usually 4 daily train trips available from Chicago to San Jose. Traveling by train from Chicago to San Jose usually takes 69 hours and 37 minutes, but the fastest Amtrak train can make the trip in 54 hours and 41 minutes.

Distance: 1838 mi (2958 km)
Fastest train: 54h 41m
Lowest price: TRY 12,785.80
Trains per day: 0
Most frequent service: Amtrak
Train lines: 1

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Chicago to San Jose Train Schedule

Is it better to travel by bus or train from Chicago to San Jose?

There are usually 4 daily bus trips available from Chicago to San Jose.

	Train	Bus
Avg. Price	Avg. PriceTRY 22,750.92	Avg. PriceTRY 16,657.65Cheaper
Daily Trips	Daily Trips4	Daily Trips4
Duration	Duration69h 37m	Duration59h 6mFaster

There are several train options that can take you from Chicago to San Jose:

Amtrak tickets: TRY 11,663 one-way

See more details

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

In the last month, the average price of a train ticket from Chicago to San Jose was TRY 17,350.14. Considering the distance between Chicago and San Jose, tickets on this route are relatively expensive. Good news! You can find the cheapest tickets if you book your trip at least 29 days prior to the travel date. You’ll likely pay around TRY 19,960.98 more if you wait to book until the last minute.

Average train ticket prices from Chicago to San Jose by travel date

Over the next 30 days, a one-way train trip from Chicago to San Jose will cost between TRY 14,396 and TRY 28,158. Book in advance to secure the best price in the next few weeks.

Average train ticket prices from Chicago to San Jose by month

Ticket prices for the train from Chicago to San Jose often fluctuate based on the time of year. For the best prices on this route, book in October when the average ticket price is only TRY 17,373. If you're thinking of traveling from Chicago to San Jose during June, keep in mind that train ticket prices may be higher than usual, with an average price of TRY 25,474 during this time of year. The best way to score a cheap deal, even in June, is to book your trip well in advance.

Prices as travel date approaches

By booking your train trip from Chicago to San Jose on Wanderu at least 29 days ahead of time, you can save about TRY 19,960.98 on your ticket. Waiting until the last minute means missing out on these savings!

Which train should you take from Chicago to San Jose?

Amtrak is the one and only train line which connects Chicago to San Jose. However, there are 4 trains per day to choose from.

Train	Daily Trips	Avg. Time	Avg. Price
Amtrak	4	69h 37m	TRY 22,750.87

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 4 Amtrak trains from Chicago to San Jose every day, as well as 4 trips on the weekends, with prices starting from TRY 11,663.38.

Frequently asked questions about traveling by train from Chicago to San Jose

There are 4 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 San Jose to Chicago. If you're not set on traveling by train, you could always take the bus from Chicago to San Jose for TRY 10,343.

Trains per day

Direct trains

The distance between Chicago and San Jose is approximately 1838 miles, or 2958 kilometers. The average train journey between these two cities takes 69 hours and 37 minutes, although the absolute fastest you could get there is 54 hours and 41 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.

Distance (mi)

1838

Distance (km)

2958

The earliest train departs Chicago at 1:30pm while the last train of the day leaves at 3:05pm. To see all scheduled departure times, use the search function on this page to get the full schedule for your specific travel dates.

First train

1:30pm

Last train

3:05pm

Trains from Chicago to San Jose are the most crowded on Tuesday. 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 Wednesday instead, as it tends to be the least crowded day of the week.

Busiest

Tuesday

Least crowded

Wednesday

City Information

Chicago

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 and a top destination in Illinois.

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.

San Jose

San Jose is located in the heart of the world-famous Silicon Valley in California’s Bay Area. It is the largest city in Northern California and, as such, it is the area’s cultural, political and financial center.

While you’re in San Jose, make sure to check out the city’s various museums. Since you’re in the world’s foremost technology hub, the Tech Museum of Innovation is a must-visit. And since you’re on the West Coast, you should stop by the San Jose Museum of Art that features the largest permanent collection of works from West Coast artists.

Thanks to its mild California climate, San Jose is one of the best cities in the U.S. for outdoor activities, and due to its largely younger-leaning population, it offers quite the vibrant nightlife. In fact, San Jose is among the biggest party hubs in America.

San Jose is served by various bus carriers and has several Amtrak stops within its vicinity. In addition, the city’s airport is located right near the downtown area, which makes travel to and from San Jose a breeze.

Station Information

Where is the train station in Chicago?

Main departure station: Union Station

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.

All train stations in Chicago:

Union Station

Where is the train station in San Jose?

Main arrival station: Diridon Caltrain Station - 65 Cahill St

Diridon Caltrain Station - 65 Cahill St - SJCDCS-0

Diridon Station opened in 1935 with architecture inspired by the Italian Renaissance, and today is a vital part of Silicon Valley’s transportation system. Diridon Station connects Amtrak train service to local commuter service like the Caltrain and VTA Light Rail. The station is also a major hub for bus transit on Amtrak Thruway and Greyhound buses. With paid parking onsite, bicycle racks, and accessible entrances, travelers can easily reach the station from nearby downtown San Jose. As a bonus, food trucks frequently set up outside the station to provide delicious cheap eats for passengers.

All train stations in San Jose:

Diridon Caltrain Station - 65 Cahill St

Need a return trip from San Jose to Chicago?

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