Travel Information to Chicago, IL from San Jose, CA
| 1833 miles (2956 km) | |
| Train, flight or bus | |
| $59 - $179 | |
| Flight • $59 (€53) • 6 h 25 min | |
| Flight • $59 (€53) • 6 h 25 min | |
| Greyhound, United or Amtrak |
Travel 1833 miles (2956 km) by train, flight or bus from San Jose, CA to Chicago, IL. The most popular travel companies which serve this route are Greyhound, United or Amtrak among others. Travelers can even take a direct bus, flight or train from San Jose, CA to Chicago, IL.
Travel optionsfrom San Jose, CA to Chicago, IL
How to get from San Jose, CA to Chicago, IL by train, bus or flight.
Our recommendation
The best way to travel from San Jose, CA to Chicago, IL is by taking a bus because it’s the best combination of price and speed.

Cheapest

Fastest

Find all the dates and times for this journey by train, bus, flight, and ferry .
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FAQs: Travel from San Jose, CA to Chicago, IL
Travel to Chicago, IL easily. Whether you want fast, cheap or something entirely different, our travel experts have collected everything you need to know so you can find the best option from San Jose, CA to Chicago, IL.

There are 3 options to travel from San Jose, CA to Chicago, IL including taking a train, flight or bus.
The cheapest way to go to Chicago, IL from San Jose, CA is by taking a flight, which costs on average $59 (€53).
This is compared to other ways of getting from San Jose, CA to Chicago, IL:
A flight is $68 (€62) less than a bus with an average ticket price of $127 (€115) from San Jose, CA to Chicago, IL.
A flight is $120 (€108) less than a train with an average ticket price of $179 (€161) from San Jose, CA to Chicago, IL.
The fastest way to get to Chicago, IL from San Jose, CA is by flight with an average travel time of 6 h 25 min.
Other travel options to Chicago, IL take longer:
Getting to Chicago, IL by bus takes 59 h 25 min on average.
Train takes 54 h 32 min on average.
The distance is approximately 1833 miles (2956 km) from San Jose, CA to Chicago, IL.
The average frequency per day from San Jose, CA to Chicago, IL is:
- 7 buses per day.
- 30 flights per day.
- 6 trains a day.
However, we recommend checking specific travel dates for your trip from San Jose, CA to Chicago, IL as scheduled services by train, flight or bus can vary by season or day of the week.
These are the most popular departure and arrival points when traveling from San Jose, CA to Chicago, IL:
The following travel companies offer services from San Jose, CA to Chicago, IL:
- Travel with Greyhound to go to Chicago, IL by bus. For a good deal on tickets, you can find Greyhound San Jose, CA to Chicago, IL tickets on Omio for $127 (€115).
- Travel with United to go to Chicago, IL by plane. For a good deal on tickets, you can find United San Jose, CA to Chicago, IL tickets on Omio for $530 (€478).
- Amtrak can get you to Chicago, IL by train. You can find a good deal for train tickets with Amtrak from San Jose, CA to Chicago, IL for $179 (€161) on Omio.
Yes, there are direct services available from San Jose, CA to Chicago, IL with the following travel companies:
- Direct flights with with 1 direct flight per day.
Direct services tend to save you time and add more convenience in getting you to Chicago, IL as you won't need to transfer at another stop in between, so it's worth paying attention to before booking your tickets to Chicago, IL from San Jose, CA.
Travelling from San Jose, CA to Chicago, IL: related information
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