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 | ||||
| Train | Diridon Station | Chicago (Union Station), IL | No tags | ||||
| Train | Diridon Station | Chicago (Union Station), IL | No tags |
Last refresh of the prices: Last Saturday at 8:42 AM 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 35 minutes and with fares starting at just R 2 747, it presents an excellent value for a comfortable ride.
Train Companies
Based on 5583 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 2 961
Where are the popular train stations and stops in San Jose, US and Chicago?
Frequently asked questions on the trip San Jose, US - Chicago
How much does a cheap train ticket from San Jose to Chicago cost?
The average train ticket price from San Jose to Chicago is R 6 808. The best way to find cheap train tickets from San Jose to Chicago is to book your tickets as early as possible. Prices tend to rise as your travel date approaches, so book in advance to secure the best prices!
How long is the train trip from San Jose to Chicago?
A train trip between San Jose and Chicago is around 2d 18h, although the fastest train will take about 2d 6h. This is the time it takes to travel the 2960 km that separates the two cities.
How many daily train are there between San Jose and Chicago?
The number of trains from San Jose to Chicago can differ depending on the day of the week. On average, there are 2. Some trains are direct while others include transferring trains. Simplify your train trip from San Jose to Chicago by comparing and selecting the train that fits your travel style and budget on Busbud.
Which train companies travel from San Jose to Chicago?
When taking the train from San Jose to Chicago, you can travel comfortably and safely with Amtrak.
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 12 Nov 2025 with a price of R 4 752To 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 4 752 to R 49 233 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 4 752, which is on 2025-11-17.
Top Travelled Train Routes
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