Next train departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Train | Diridon Station | Chicago (Union Station), IL | CheapestFastest | ||||
| Train | Diridon Station | Chicago (Union Station), IL | No tags |
Last refresh of the prices: Last Tuesday at 7:09 PM PST.
Compare 2 ways to travel from San Jose to Chicago
Among the sustainable travel choices, the bus stands out as a good way to reach Chicago. The journey takes about 2 days, 13 hours 25 minutes and with fares starting at just R 1 861, it presents an excellent value for a comfortable ride.
Where are the popular train stations and stops in San Jose, US and Chicago?
Chicago
- A
Union Station
225 S Canal St, Chicago, IL 60606, USA
Train Companies
Based on 5639 reviews, the company was rated 4.1 stars on Busbud. Travellers were especially satisfied with the seats and the ticket access but often complained with the Wi-Fi. Amtrak ticket prices on this trip start at R 2 920
Frequently asked questions about travelling from San Jose, US to Chicago by train
Please note that timetables, routes, or operator details shown here may be updated or differ at the time of your trip.
How much is the train ticket from San Jose to Chicago?
The cheapest train tickets from San Jose to Chicago start from R 2 920. The average price for this train route is around R 7 357. Busbud recommends booking your tickets in advance for a better chance to secure the lowest possible price.
How long is the train journey from San Jose to Chicago?
The average train journey time from San Jose to Chicago is 2d 18h, covering a distance of 2959 km. The quickest train can get you there in 2d 6h and is operated by Amtrak.
Which train operators serve the San Jose to Chicago route?
Several major train operators run on this route, with 2 trains available per day.
What are the earliest and latest departure times for the train from San Jose to Chicago?
The earliest train from San Jose to Chicago departs at 06:18. And the latest train departs at 19:58.
Find cheapest prices for trains
Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from San Jose, US to Chicago was searched and found on 15 Dec 2025 with a price of R 3 268To save money and be sure you have the best seat, it's a good idea to buy your train tickets from San Jose, US to Chicago as early as possible.
You can expect to pay from R 3 268 to R 54 491 for a train ticket from San Jose, US to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at R 3 268, which is on 2025-12-15.
