How to travel from San Jose, CA to Chicago, IL

Sun, Jul 21
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Travel Information from San Jose, CA to Chicago, IL

distanceDistance1833 miles (2956 km)
modeAvailable travel modesBus, train or flight
priceTicket price range$85 - $185
cheapestCheapest modeFlight • $85 (€73) • 5 h 45 min
fastestFastest modeFlight • $85 (€73) • 5 h 45 min
carriersPopular travel companiesGreyhound, United or Amtrak

Travel 1833 miles (2956 km) by bus, train or flight between San Jose, CA and Chicago, IL. The most popular travel companies which serve this trip 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 options
from San Jose, CA to Chicago, IL

How to get from San Jose, CA to Chicago, IL by train, bus or flight.

Our recommendation
bus

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.

Greyhound
08:50PM71h25
San Jose, CA
08:15PMChicago, IL
$2871One-way
0 transfers
Cheapest
Greyhound
08:50PM71h25
San Jose, CA
08:15PMChicago, IL
$2871One-way
0 transfers
Fastest
Greyhound
08:50PM71h25
San Jose, CA
08:15PMChicago, IL
$2871One-way
0 transfers

Find all the dates and times for this journey by train, bus, flight, and ferry .

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All travel companies: Airlines, Train and Bus from San Jose to Chicago

Find the best route from San Jose to Chicago with Omio's travel partners Amtrak, American Airlines and United! You'll find the best deals, schedules and tickets when comparing and booking the most affordable journey for you.

Amtrak is the main travel company in the United States operating medium and long-distance intercity services in 46 US states as well as in 3 Canadian provinces. There are over 300 Amtrak travel running daily. With Amtrak you can travel by travel across the country and explore destinations near and far with routes such as the Northeast Regional connecting cities in the East Coast, the Coast Starlight connecting destinations up and down the West Coast, the Empire Builder connecting Chicago and Midwestern cities to the Northwest, and many more. Amtrak offers different class options suiting any budget, from Coach Class to Business Class, First Class, and the Sleeper Class, where you can book a Roomette, Bedroom, and Bedroom suite among others for night travel. There are several different ticket types including Saver, Value, Flexible, Business and Premium for you to book for your next travel journey to Chicago from San Jose.

      American Airlines is one of the leading airlines in the USA and the world; they offer Main Cabin, Business and First Class tickets for your travel from San Jose to Chicago.

        FAQs: Travel from San Jose, CA to Chicago, IL

        FAQs: 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.
        FAQs

        You can get to Chicago, IL from San Jose, CA 3 different ways: bus, train or flight.

        The cheapest way to travel from San Jose, CA to Chicago, IL is a flight with an average price of $85 (€73).

        This is compared to other travel options from San Jose, CA to Chicago, IL:

        A flight is $100 (€87) less than a bus for this route with tickets for a bus from San Jose, CA to Chicago, IL costing on average $185 (€160).

        A flight is $73 (€63) less than a train for this trip with tickets for a train from San Jose, CA to Chicago, IL costing on average $158 (€136).

        The fastest way from San Jose, CA to Chicago, IL is by flight with an average journey time of 5 h 45 min.

        There are alternative travel options to Chicago, IL that take longer:

        Getting to Chicago, IL by bus takes 53 h 55 min on average.

        Train takes 54 h 40 min on average.

        You should expect to travel around 1833 miles (2956 km) between San Jose, CA and Chicago, IL.

        The average frequency per day from San Jose, CA to Chicago, IL is:

          However, we recommend checking specific travel dates for your route from San Jose, CA to Chicago, IL as scheduled services by bus, train or flight 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 for buses to Chicago, IL. If you’re looking for a good deal on tickets, check for Greyhound San Jose, CA to Chicago, IL tickets on Omio for $188 (€162).
            • Travel with United or American Airlines 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 $555 (€478).
            • Travel with Amtrak to go to Chicago, IL by train. For a good deal on tickets, you can find Amtrak San Jose, CA to Chicago, IL tickets on Omio for $158 (€136).

            Yes, there are direct routes from San Jose, CA to Chicago, IL with the following travel companies:

            • You can book a direct bus with.
            • You can book a direct flight with.
            • You'll find direct trains with.

            Direct services to Chicago, IL tend to save you time and add more convenience as you won't need to transfer at another stop in between, so it's worth paying attention to before booking tickets for your journey.

            Many of our customers who book a trip from San Jose, CA to Chicago, IL often extend their vacation and travel to other popular destinations like San Francisco, CA, Indianapolis, IN, New York, NY, Milwaukee, WI or Champaign, IL. If you’re thinking of adding another destination to your San Jose, CA and Chicago, IL itinerary, let Omio find you the best connections between Chicago, IL and any of these top destinations today!

            Travel to popular destinations by train, bus or flight

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