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How to get fromSan Jose Airport (SJC) to Chicagoby plane, subway, bus, train, or car

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There are 8 ways to get from San Jose Airport (SJC) to Chicago by plane, subway, bus, train, 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 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
    4h 41m
    $141–563

  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
    5h 10m
    $119–479

  3. Fly San Francisco International Airport to Chicago Midway International Airport

    1. Fly from San Francisco International Airport (SFO) to Chicago Midway International Airport (MDW)plane plane SFO - MDW
    6h 36m
    $220–458

  4. BART, bus

    1. Take the subway from Milpitas to El Cerrito Del Nortesubway subway
    2. Take the bus from El Cerrito del Norte Station to Suisun-Fairfield Amtrak Stationbus bus 90 / ...
    3. Take the bus from Suisun City Bus Stop to Sparks Transit Centerbus bus
    4. Take the bus from Sparks Transit Center to Denver Union Stationbus bus
    5. Take the bus from Denver Union Station to Chicago Bus Stationbus bus
    2d 4h
    $342–664

  5. BART, train

    1. Take the subway from Milpitas to Richmondsubway subway Orange-N
    2. Take the train from Richmond to Chicago Union Stationtrain train California Zephyr
    2d 7h
    $760–1,614

  6. Fly San Francisco International Airport to Chicago O'Hare International Airport

    1. Fly from San Francisco International Airport (SFO) to Chicago O'Hare International Airport (ORD)plane plane SFO - ORD
    7h
    $160–328

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

    1. Take the subway from Milpitas to Coliseumsubway subway
    2. Fly from Oakland International Airport (OAK) to Chicago Midway International Airport (MDW)plane plane OAK - MDW
    7h 11m
    $152–618

  8. Drive 2,154.2 mi

    1. Drive from San Jose Airport (SJC) to Chicagocar car 2,154.2 mi
    33h 26m
    $394–568

San Jose Airport (SJC) to Chicago by bus and subway

Calendar14Weekly Services
Duration2d 4hAverage Duration
Ticket$342Cheapest Price
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Questions & Answers

Map of how to get from San Jose Airport (SJC) to Chicago.ExpandLaunch map view
  • Distance: 1,844.6 mi
  • Duration: 4h 41m

What companies run services between San Jose Airport (SJC), 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.

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