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How to get fromCupertino to Chicagoby plane, bus (Greyhound), train, subway, or car

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There are 8 ways to get from Cupertino to Chicago by plane, bus (Greyhound), train, subway, 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
    6h 52m
    $130–568

  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
    7h 18m
    $120–478

  3. Bus

    1. Take the bus from San Jose Park and Ride to Heavenly Valley Ski Lodgebus bus
    2. Take the bus from Gardnerville - Smith's, 1341 US 395 to Reno - RTC Centennial Plaza Bay "O" - 1421 Victorian Avenue, Sparks, NV 89431bus bus 395
    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 4h
    $496–812

  4. Caltrain, BART, train

    1. Take the train from Sunnyvale Caltrain Northbound to Millbrae Caltrain Northboundtrain train
    2. Take the subway from Millbrae to Richmondsubway subway
    3. Take the train from Richmond to Chicago Union Stationtrain train
    2d 7h
    $620–1,529

  5. Drive  2,159.7 mi

    1. Drive from Cupertino to Chicagocar car 2,159.7 mi
    33h 32m
    $395–570

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

    1. Take the train from Sunnyvale 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
    7h 10m
    $188–439

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

    1. Take the train from Sunnyvale 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 28m
    $138–309

  8. Train to Oakland International Airport, fly to Chicago Midway International Airport

    1. Take the train from Santa Clara Amtrak to Oakland Coliseum/Airport Amtraktrain train
    2. Fly from Oakland International Airport (OAK) to Chicago Midway International Airport (MDW)plane plane OAK - MDW
    8h 8m
    $146–632

Cupertino to Chicago by bus, train, and subway

Calendar7Weekly Services
Duration2d 7hAverage Duration
Ticket$620Cheapest Price
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Questions & Answers

Map of how to get from Cupertino to Chicago.ExpandLaunch map view
  • Distance: 1,859.5 mi
  • Duration: 6h 52m

What companies run services between Cupertino, 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 McClellan & Felton to Chicago Bus Station via Tamien Station, San Jose Park and Ride, Heavenly Valley Ski Lodge, Gardnerville - Smith's, 1341 US 395, Reno - RTC Centennial Plaza Bay "O" - 1421 Victorian Avenue, Sparks, NV 89431, Sparks Transit Center, and Denver Union Station in around 2d 4h.

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