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How to get fromSan Jose to Chicago Midway Airport (MDW)by plane, train (Amtrak), car, subway, train, or bus

Find Transport to Chicago Midway Airport (MDW)

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

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 6m
    $132–602

  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 45m
    $116–502

  3. 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 7h
    $720–1,639

  4. Drive 2,148.6 mi

    1. Drive from San Jose to Chicago Midway Airport (MDW)car car 2,148.6 mi
    33h 26m
    $393–567

  5. 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
    5h 57m
    $139–612

  6. 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 6m
    $186–460

  7. 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 40m
    $140–310

  8. 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 3m
    $183–689

  9. Bus, train

    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 Salt Lake City Intermodal Trans Ctrbus bus
    4. Take the train from Salt Lake City to Chicago Union Stationtrain train
    2d 7h
    $598–1,333

San Jose to Chicago Midway Airport (MDW) by train, bus, and subway (Amtrak)

Calendar7Weekly Services
Duration2d 7hAverage Duration
Ticket$720Cheapest Price
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Questions & Answers

Map of how to get from San Jose to Chicago Midway Airport (MDW).ExpandLaunch map view
  • Distance: 1,835.2 mi
  • Duration: 5h 6m

What companies run services between San Jose, CA, USA and Chicago Midway Airport (MDW), 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 train from San Jose to Midway via Emeryville, Chicago Union Station, Jackson & Clinton, Jackson & Wabash, and Adams/Wabash in around 2d 7h.

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