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How to get fromSan Jose to Chicagoby plane, bus (Greyhound, Flixbus), train (Amtrak), car, subway, or train

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There are 9 ways to get from San Jose to Chicago by plane, bus (Greyhound, Flixbus), train (Amtrak), car, subway, or train

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

    best
    1. Fly from Norman Y. Mineta San José International Airport (SJC) to Chicago Midway International Airport (MDW)plane plane SJC - MDW
    5h 47m
    $134–558

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

    cheapest
    1. Fly from Norman Y. Mineta San José International Airport (SJC) to Chicago O'Hare International Airport (ORD)plane plane SJC - ORD
    6h 16m
    $114–488

  3. Bus

    1. Take the bus from San Jose Diridon Station to Oaklandbus bus
    2. Take the bus from Oakland to Sparks Transit Centerbus bus
    3. Take the bus from Sparks Transit Center to Denver Union Stationbus bus
    4. Take the bus from Denver Union Station to Chicago Bus Stationbus bus
    2d 3h
    $326–642

  4. Train (Amtrak)

    1. Take the train from San Jose to Emeryvilletrain train Capitol Corridor / ...
    2. Take the train from Emeryville to Chicago Union Stationtrain train California Zephyr
    2d 6h
    $664–1,530

  5. Drive 2,154.1 mi

    1. Drive from San Jose to Chicagocar car 2,154.1 mi
    33h 24m
    $394–568

  6. BART to Oakland International Airport, fly to Chicago Midway International Airport

    1. Take the subway from Berryessa / North San Jose to Coliseumsubway subway
    2. Fly from Oakland International Airport (OAK) to Chicago Midway International Airport (MDW)plane plane OAK - MDW
    6h 38m
    $151–617

  7. Caltrain to San Francisco International Airport, fly to Chicago Midway International Airport

    1. Take the train from San Jose Diridon Caltrain Northbound to Millbrae Caltrain Northboundtrain train
    2. Fly from San Francisco International Airport (SFO) to Chicago Midway International Airport (MDW)plane plane SFO - MDW
    6h 48m
    $188–435

  8. Caltrain to San Francisco International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from San Jose Diridon Caltrain Northbound to Millbrae Caltrain Northboundtrain train
    2. Fly from San Francisco International Airport (SFO) to Chicago O'Hare International Airport (ORD)plane plane SFO - ORD
    7h 6m
    $138–305

  9. Train to Sacramento International Airport, fly to Chicago Midway International Airport

    1. Take the train from San Jose to Sacramentotrain train
    2. Fly from Sacramento International Airport (SMF) to Chicago Midway International Airport (MDW)plane plane SMF - MDW
    9h 45m
    $172–641

San Jose to Chicago by bus

Calendar7Weekly Buses
Duration2d 3hAverage Duration
Ticket$326Cheapest Price
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Questions & Answers

Map of how to get from San Jose to Chicago.ExpandLaunch map view
  • Distance: 1,846.2 mi
  • Duration: 5h 47m

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

Southwest Airlines flies from Norman Y. Mineta San José International Airport (SJC) to Chicago Midway International Airport (MDW) 5 times a day. Alternatively, you can take a bus from San Jose Diridon Station to Chicago Bus Station via Oakland, Sparks Transit Center, and Denver Union Station in around 2d 3h.

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