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

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There are 8 ways to get from Sunnyvale to Chicago by plane, bus (Greyhound, Flixbus), 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 19m
    $209–863

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

    cheapest
    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
    6h 51m
    $116–423

  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 4h
    $340–663

  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
    $719–1,523

  5. Drive 2,156.7 mi

    1. Drive from Sunnyvale to Chicagocar car 2,156.7 mi
    33h 27m
    $394–569

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

    1. Fly from Norman Y. Mineta San José International Airport (SJC) to Chicago O'Hare International Airport (ORD)plane plane SJC - ORD
    6h 42m
    $159–663

  7. 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
    6h 44m
    $146–573

  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
    7h 57m
    $188–737

Sunnyvale to Chicago by train and bus

Calendar7Weekly Services
Duration2d 4hAverage Duration
Ticket$340Cheapest Price
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Questions & Answers

Map of how to get from Sunnyvale to Chicago.ExpandLaunch map view
  • Distance: 1,854.4 mi
  • Duration: 6h 19m

What companies run services between Sunnyvale, 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 train from Sunnyvale Caltrain Southbound to Chicago Bus Station via San Jose Diridon Caltrain Southbound, San Jose Diridon Station, Oakland, Sparks Transit Center, and Denver Union Station in around 2d 4h.

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