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

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There are 8 ways to get from Sunnyvale to Chicago by plane, train, subway, bus (Greyhound, Flixbus), 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 14m
    $209–963

  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 48m
    $91–383

  3. 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
    $619–1,423

  4. Bus

    1. Take the bus from San Jose - King Rd Pink Elephant to 285 S East End Ave - Pomonabus bus
    2. Take the bus from Montclair Transcenter to St Louis Bus Stationbus bus
    3. Take the bus from St Louis Bus Station to Chicago Bus Stationbus bus
    2d 11h
    $428–791

  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 41m
    $119–563

  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 34m
    $146–673

  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 53m
    $186–834

Sunnyvale to Chicago by train and subway

Calendar7Weekly Services
Duration2d 7hAverage Duration
Ticket$619Cheapest Price
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Questions & Answers

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) every 4 hours. Alternatively, you can take a bus from El Camino & Mathilda to Chicago Bus Station via King & Virginia, San Jose - King Rd Pink Elephant, 285 S East End Ave - Pomona, East End Ave and Mission Blvd E, Montclair Transit Center, Montclair Transcenter, and St Louis Bus Station in around 2d 11h.

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