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How to get fromChicago to San Joseby plane, train, subway, bus (Flixbus, Greyhound), or car

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There are 8 ways to get from Chicago to San Jose by plane, train, subway, bus (Flixbus, Greyhound), or car

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Fly Chicago Midway International Airport to Norman Y. Mineta San José International Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Norman Y. Mineta San José International Airport (SJC)plane plane MDW - SJC
    6h 18m
    $206–858

  2. Fly Chicago O'Hare International Airport to San Francisco International Airport, Caltrain

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to San Francisco International Airport (SFO)plane plane ORD - SFO
    2. Take the train from Millbrae Caltrain Southbound to San Jose Diridon Caltrain Southboundtrain train
    7h 46m
    $138–306

  3. Train, BART

    1. Take the train from Chicago Union Station to Richmondtrain train California Zephyr
    2. Take the subway from Richmond to Berryessa / North San Josesubway subway Orange-S
    2d 6h
    $798–1,592

  4. Bus

    1. Take the bus from Chicago Bus Station to St Louis Bus Stationbus bus
    2. Take the bus from St Louis Bus Station to Los Angeles Union Stationbus bus
    3. Take the bus from Los Angeles Union Station to San Jose Diridon Stationbus bus
    2d 6h
    $400–792

  5. Drive 2,154 mi

    1. Drive from Chicago to San Josecar car 2,154 mi
    33h 23m
    $394–568

  6. Fly Chicago O'Hare International Airport to Norman Y. Mineta San José International Airport

    1. Fly from Chicago O'Hare International Airport (ORD) to Norman Y. Mineta San José International Airport (SJC)plane plane ORD - SJC
    6h 50m
    $166–558

  7. Fly Chicago Midway International Airport to Oakland International Airport, BART

    1. Fly from Chicago Midway International Airport (MDW) to Oakland International Airport (OAK)plane plane MDW - OAK
    2. Take the subway from Coliseum to Berryessa / North San Josesubway subway
    7h 4m
    $230–917

  8. Fly Chicago Midway International Airport to San Francisco International Airport, Caltrain

    1. Fly from Chicago Midway International Airport (MDW) to San Francisco International Airport (SFO)plane plane MDW - SFO
    2. Take the train from Millbrae Caltrain Southbound to San Jose Diridon Caltrain Southboundtrain train
    7h 26m
    $218–466

Chicago to San Jose by train and subway

Calendar7Weekly Services
Duration2d 6hAverage Duration
Ticket$798Cheapest Price
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Questions & Answers

Map of how to get from Chicago to San Jose.ExpandLaunch map view
  • Distance: 1,846.6 mi
  • Duration: 6h 18m

What companies run services between Chicago, IL, USA and San Jose, CA, USA?

Southwest Airlines flies from Chicago Midway International Airport (MDW) to Norman Y. Mineta San José International Airport (SJC) 5 times a day. Alternatively, you can take a bus from Chicago Bus Station to San Jose Diridon Station via St Louis Bus Station and Los Angeles Union Station in around 2d 6h.

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