The cheapest and fastest trains from San Jose, CA to Chicago, IL
Cheapest price
$296
Average price
$526
Fastest journey
2 d 6 h 22 m
Average duration
2 d 11 h 6 m
Trains per day
3
Distance
2957 km
The best way to find a cheap train ticket from San Jose, CA to Chicago, IL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from San Jose, CA to Chicago, IL will cost around $526 if you buy it on the day, but the cheapest tickets can be found for only $296.
Of the 3 trains that leave San Jose, CA for Chicago, IL on Sun, Mar 22, 3 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Sun, Mar 22 the direct trains cover the 2957 km distance in an average of 2 d 11 h 6 m but if you time it right, some trains will get you there in just 2 d 6 h 22 m .
On Sun, Mar 22 the slowest trains will take 2 d 18 h 47 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.






Travel Information
Compare train, bus, and flight for San Jose, CA to Chicago, IL
Omio recommends booking the train as it is the most popular option from San Jose, CA to Chicago, IL among Omio's users. If you are prioritising price take the train with prices starting from $170. For those with little time consider booking a flight which can get you there in 4h 55m. In case you are seeking to minimise your carbon footprint the train is your best bet as it emits only 0.9 - 2.7kg. The ticket price range depends on the travel mode: a train costs an average of $170, and a flight costs an average of $165.
Distance: 1837 miles (2957 km)
Compare train with
Most popular Train | Flight | Bus |
|---|---|---|
$380 Average price Cheapest | $432 Average price | $391 Average price |
58h 26m Average total duration 57h 56m Onboard + 30m Additional time* | 7h 55m Average total duration Fastest 4h 55m Onboard + 3h 0m Additional time* | 60h 22m Average total duration 59h 52m Onboard + 30m Additional time* |
0.9 - 2.7kg CO2 emissions Lowest | 8.9 - 17.7kg CO2 emissions | 3.0 - 7.4kg CO2 emissions |
Direct Options | Direct Options | Direct Options |
Additional time: Average total travel duration to departure point, security checks and transfers.
Live departures
San Jose, CA to Chicago, IL train times
The table below shows live departures for San Jose, CA to Chicago, IL trains for tomorrow, Saturday, March 21. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 3:58 AM San Jose, CA | 66h47 | 10:45 PM Chicago, IL | 0 transfersDirect | |
![]() | 12:30 PM San Jose, CA | 56h09 | 8:39 PM Chicago, IL | 0 transfersDirect | |
This is the last train of the day. | |||||
Find all the dates and times for this journey
Compare prices and tickets San Jose, CA to Chicago, IL by train, bus, or flight
Compare train, bus, and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
Mar 22
Mar 23
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Mar 27
Mar 28
Journey information
Overview: Train from San Jose, CA to Chicago, IL
Trains from San Jose, CA to Chicago, IL run on average 5 times per day, taking around 57h 56m. Cheap train tickets for this journey start at $170 (€137) but you can travel from only $155 (€126) by bus.
The earliest train runs at 04:30, the last at 23:45. The fastest train covers the 1837 miles (2957 km) distance in 54h 14m.
Distance 1837 miles (2957 km) |
Average train duration 57h 56m |
Cheapest ticket price $170 (€137) |
Trains per day 5 |
Fastest train 54h 14m |
First train 04:30 |
Last train 23:45 |
Cheapest month May |
Cheapest day Wed |
High season Oct - Dec |
Low season Apr - Jun |
Best day to book ahead 14 days |
Train companies: Amtrak from San Jose, CA to Chicago, IL trainsAmtrak trains will get you between San Jose, CA and Chicago, IL from $155 (€126). With over 1000 travel companies on Omio, you can find the best train times and tickets for your trip.
Amtrak
FAQs: Trains from San Jose, CA to Chicago, IL
Find answers to the most common questions about traveling from San Jose, CA to Chicago, IL by train. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest train, the cheapest option, or tips for making the most of your visit at Chicago, IL, this guide helps you travel smarter and with confidence.

popular train stations
Popular train stations from San Jose, CA to Chicago, IL
- 6:00 AM - 10:00 PM Monday - Sunday
- Parking is available 7 days a week, with multiple lots surrounding the station.
- The Farmers Union
- Poor House Bistro
- La Victoria Taqueria
- Outside the main entrance.
- Elevators, ramps, restrooms.
- $0.50
- Hotel De Anza
- The Westin San Jose
- AC Hotel by Marriott San Jose Downtown
- Located in the main hall
- Enterprise
- Hertz
- Located in the main hall
- Free
- The station has a main hall with ticketing and waiting areas, platforms for Caltrain, Amtrak, and ACE services, and connections to VTA buses and light rail.
- Bus: VTA Bus Lines 22, 64A, 64B, 68, 168, 181
- Light Rail: VTA Green Line
- Caltrain
- Amtrak
- ACE
- 5:00 AM - 12:00 AM Monday - Sunday
- Free
- The car park is open 7 days a week from 5:00 a.m. to 12:00 a.m. Departures can be made outside of opening hours. Access via Canal Street.
- The Chicago Firehouse Restaurant
- Lou Mitchell's
- Outside the main entrance.
- Elevators, ramps, restrooms.
- $1
- The Kimpton Gray Hotel
- JW Marriott Chicago
- W Chicago - City Center
- Located in the main hall
- Located in the main hall
- Avis
- Budget
- Enterprise
- Located in the main hall
- Free
- Hall 1: main entrance, Amtrak services
- Hall 2: Metra services
- Hall 3: food court and retail shops
- Bus: Several lines available
- CTA: Blue Line, Pink Line
Most popular train connections from San Jose, CA
More options for your journey from San Jose, CA to Chicago, IL
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