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How to get fromChicago to Sunnyvaleby plane, bus (Greyhound, Flixbus), train, subway, or car

Find Transport to Sunnyvale

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There are 8 ways to get from Chicago to Sunnyvale 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 Chicago Midway International Airport to Norman Y. Mineta San José International Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Norman Y. Mineta San José International Airport (SJC)plane plane MDW - SJC
    7h 5m
    $198–863

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

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to San Francisco International Airport (SFO)plane plane ORD - SFO
    2. Take the train from Millbrae Caltrain Southbound to Sunnyvale Caltrain Southboundtrain train
    7h 37m
    $92–375

  3. Bus

    1. Take the bus from Chicago Bus Station to Denver Union Stationbus bus
    2. Take the bus from Denver Union Station to Sparks Transit Centerbus bus
    3. Take the bus from Sparks Transit Center to Oaklandbus bus
    4. Take the bus from Oakland to San Jose Diridon Stationbus bus
    2d 4h
    $428–643

  4. Train, BART, Caltrain

    1. Take the train from Chicago Union Station to Richmondtrain train
    2. Take the subway from Richmond to Millbraesubway subway
    3. Take the train from Millbrae Caltrain Southbound to Sunnyvale Caltrain Southboundtrain train
    2d 7h
    $1,333–2,043

  5. Drive  2,156.2 mi

    1. Drive from Chicago to Sunnyvalecar car 2,156.2 mi
    33h 25m
    $369–533

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Norman Y. Mineta San José International Airport (SJC)plane plane ORD - SJC
    7h 27m
    $118–503

  7. Fly Chicago Midway International Airport to San Francisco International Airport, Caltrain

    1. Fly from Chicago Midway International Airport (MDW) to San Francisco International Airport (SFO)plane plane MDW - SFO
    2. Take the train from Millbrae Caltrain Southbound to Sunnyvale Caltrain Southboundtrain train
    7h 32m
    $146–435

  8. Fly Chicago Midway International Airport to Oakland International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Oakland International Airport (OAK)plane plane MDW - OAK
    2. Take the train from Oakland Coliseum/Airport Amtrak to Santa Clara Amtraktrain train
    8h 48m
    $188–798

Chicago to Sunnyvale by bus and train

Calendar7Weekly Services
Duration2d 4hAverage Duration
Ticket$428Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Sunnyvale.ExpandLaunch map view
  • Distance: 1,854.8 mi
  • Duration: 7h 5m

What companies run services between Chicago, IL, USA and Sunnyvale, CA, USA?

Southwest Airlines flies from Chicago Midway International Airport (MDW) to Norman Y. Mineta San José International Airport (SJC) every 4 hours. Alternatively, you can take a bus from Chicago Bus Station to Sunnyvale Caltrain Northbound via Denver Union Station, Sparks Transit Center, Oakland, San Jose Diridon Station, and San Jose Diridon Caltrain Northbound in around 2d 4h.

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