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Cheap train tickets from San Jose to Chicago
Find and compare the best ground travel options in one place.
Trip Summary
There are usually 6 daily train trips available from San Jose to Chicago. Traveling by train from San Jose to Chicago usually takes 61 hours and 42 minutes, but the fastest Amtrak train can make the trip in 54 hours and 21 minutes.
- Distance
- 1838 mi (2958 km)
- Fastest train
- 54h 21m
- Lowest price
- RON 1,052.70
- Trains per day
- 0
- Most frequent service
- Amtrak
- Train lines
- 1
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San Jose to Chicago Train Schedule
Is it better to travel by bus or train from San Jose to Chicago?
There are usually 3 daily bus trips available from San Jose to Chicago.
Train | Bus | |
|---|---|---|
Avg. Price | Avg. PriceRON 2,235.05 | Avg. PriceRON 1,422.76Cheaper |
Daily Trips | Daily Trips6 | Daily Trips3 |
Duration | Duration61h 42mFaster | Duration65h 33m |
There are several train options that can take you from San Jose to Chicago:
See more detailsWhat is the price of a train ticket from San Jose to Chicago?
In the last month, the average price of a train ticket from San Jose to Chicago was RON 1,413.48. Considering the distance between San Jose and Chicago, tickets on this route are relatively expensive. Good news! You can find the cheapest tickets if you book your trip at least 23 days prior to the travel date. You’ll likely pay around RON 1,648.21 more if you wait to book until the last minute.
Average train ticket prices from San Jose to Chicago by travel date
Over the next 30 days, a one-way train trip from San Jose to Chicago will cost between RON 1,182 and RON 2,087. Book in advance to secure the best price in the next few weeks.
Average train ticket prices from San Jose to Chicago by month
Ticket prices for the train from San Jose to Chicago 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 RON 1,464. If you're thinking of traveling from San Jose to Chicago during December, keep in mind that train ticket prices may be higher than usual, with an average price of RON 2,410 during this time of year. The best way to score a cheap deal, even in December, is to book your trip well in advance.
Prices as travel date approaches
By booking your train trip from San Jose to Chicago on Wanderu at least 23 days ahead of time, you can save about RON 1,648.21 on your ticket. Waiting until the last minute means missing out on these savings!
Which train should you take from San Jose to Chicago?
Amtrak is the one and only train line which connects San Jose to Chicago. However, there are 6 trains per day to choose from.
| Train | Daily Trips | Avg. Time | Avg. Price |
|---|---|---|---|
| Amtrak | 6 | 61h 42m | RON 2,235.07 |
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 6 Amtrak trains from San Jose to Chicago every day, as well as 5 trips on the weekends, with prices starting from RON 1,052.70.
Frequently asked questions about traveling by train from San Jose to Chicago
There are 6 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 set on traveling by train, you could always take the bus from San Jose to Chicago for RON 715.
Trains per day
6
Direct trains
0
The distance between San Jose and Chicago is approximately 1838 miles, or 2958 kilometers. The average train journey between these two cities takes 61 hours and 42 minutes, although the absolute fastest you could get there is 54 hours and 21 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 San Jose at 4:30am while the last train of the day leaves at 11:45pm. 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
4:30am
Last train
11:45pm
Trains from San Jose to Chicago are the most crowded on Wednesday. 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 Saturday instead, as it tends to be the least crowded day of the week.
Busiest
Wednesday
Least crowded
Saturday
City Information
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.
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.
Station Information
Where is the train station in San Jose?
Main departure station: Diridon Caltrain Station - 65 Cahill St
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
Where is the train station in Chicago?
Main arrival 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
Need a return trip from Chicago to San Jose?
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