How much does a train ticket from San Jose to Chicago cost?

The average train ticket price from San Jose to Chicago is $399. The best way to find 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 1836 miles that separates the two cities.

How many daily trains 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 have layovers. 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.

What are the best sights and things to do in Chicago?

Once in Chicago, you can explore the city. The top sights and things to do are Museum of Contemporary Art, Willis Tower (Sears Tower), Chicago Shakespeare Theater on Navy Pier, Navy Pier, Lincoln Park Zoo.

Train San Jose to Chicago from $189 | Refundable Tickets

Previously seen trips

Next departures for San Jose to Chicago on November 22
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	7:58pm	Diridon Station	2d 18h	4:45pm	Chicago (Union Station), IL	No tags
Train	10:26am	Diridon Station	3d 1h	1:44pm	Chicago (Union Station), IL	No tags
Train	7:58pm	Diridon Station	2d 18h	4:45pm	Chicago (Union Station), IL	No tags
Train	10:26am	Diridon Station	3d 1h	1:44pm	Chicago (Union Station), IL	No tags
Train	6:18am	Diridon Station	2d 6h	2:39pm	Chicago (Union Station), IL	No tags

Compare 2 ways to go from San Jose to Chicago

We recommend taking the bus

Among the sustainable travel choices, the bus stands out as the good way to reach Chicago. The journey takes about 2 days, 13 hours 35 minutes and with fares starting at just $157, it presents an excellent value for a comfortable ride.

6bus per day

2d 13hAverage Duration

1835 milesDistance

74kgCO₂ emissions

	Average Price	Average Duration	CO₂ emissions	Actions
Bus	Average Price$157 - $731	Average Duration2d 13h	CO₂ emissions 74kg CO₂e
Train	Average Price$145 - $1,886	Average Duration2d 18h	CO₂ emissions 269kg CO₂e

Where are the popular train stations and stops in San Jose, US and Chicago?

San Jose, US

A
Diridon Station
65 Cahill St., San Jose, CA 95110
Visit page

Chicago

A
Union Station
225 S Canal St, Chicago, IL 60606, USA

Train Companies

Amtrak

4/55,599 reviews

Staff4.7

Timeliness3.8

Cleanliness4.6

Wifi3.6

Based on 5599 reviews, the company was rated 4.1 stars on Busbud. Travelers were especially satisfied with the seats and the ticket access but often complained with the wifi. Amtrak ticket prices on this trip start at $145

Train and bus companies in US:Amtrak, Trenitalia, Renfe, VIA Rail Canada, Amtrak Acela, NS Nederlandse Spoorwegen, Iryo

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

How much does a train ticket from San Jose to Chicago cost?
How long is the train trip from San Jose to Chicago?
How many daily trains are there between San Jose and Chicago?
Which train companies travel from San Jose to Chicago?
What are the best sights and things to do in Chicago?

Find cheapest prices for trains

Price is for a one-way ticket for one passenger and based on past searches.

Best price found

11/20

$467

11/21

$189

Today

$485

11/23

$429

11/24

$321

11/25

$271

11/26

$229

11/27

$429

The cheapest trip from San Jose, US to Chicago was searched and found on Nov 21, 2025 with a price of $189

To 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 $189 to $3,633 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 $229 which is on 2025-11-26.