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How to get fromChicago to Paradise Cayby plane, bus (Greyhound), train (Amtrak), car, bus, subway, or train

Find Transport to Paradise Cay

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There are 9 ways to get from Chicago to Paradise Cay by plane, bus (Greyhound), train (Amtrak), car, bus, subway, or train

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 Oakland International Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Oakland International Airport (OAK)plane plane MDW - OAK
    7h 40m
    $244–884

  2. Fly Chicago Midway International Airport to San Francisco International Airport, bus

    cheapest
    1. Fly from Chicago Midway International Airport (MDW) to San Francisco International Airport (SFO)plane plane MDW - SFO
    2. Take the bus from San Francisco Airport to Mill Valley P&R - dropoffbus bus
    7h 52m
    $184–501

  3. Bus (Greyhound)

    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
    2d 2h
    $504–720

  4. Train (Amtrak)

    1. Take the train from Chicago Union Station to Richmondtrain train California Zephyr
    2d 5h
    $1,374–2,094

  5. Drive  2,124.2 mi

    1. Drive from Chicago to Paradise Caycar car 2,124.2 mi
    32h 59m
    $388–560

  6. Fly Chicago O'Hare International Airport to San Francisco International Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to San Francisco International Airport (SFO)plane plane ORD - SFO
    2. Take the bus from San Francisco Airport to Mill Valley P&R - dropoffbus bus
    8h 2m
    $204–331

  7. Fly Chicago Midway International Airport to Norman Y. Mineta San José International Airport, BART

    1. Fly from Chicago Midway International Airport (MDW) to Norman Y. Mineta San José International Airport (SJC)plane plane MDW - SJC
    2. Take the subway from Milpitas to Richmondsubway subway
    8h 43m
    $248–890

  8. Fly Chicago O'Hare International Airport to Norman Y. Mineta San José International Airport, BART

    1. Fly from Chicago O'Hare International Airport (ORD) to Norman Y. Mineta San José International Airport (SJC)plane plane ORD - SJC
    2. Take the subway from Milpitas to Richmondsubway subway
    9h 6m
    $188–640

  9. Fly Chicago Midway International Airport to Sacramento International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Sacramento International Airport (SMF)plane plane MDW - SMF
    2. Take the train from Sacramento to Richmondtrain train
    9h 25m
    $290–994

Chicago Midway International Airport (MDW) to Oakland International Airport (OAK) flights

Calendar48Weekly Planes
Duration5h 54mAverage Duration
Ticket$179Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Paradise Cay.ExpandLaunch map view
  • Distance: 1,886.8 mi
  • Duration: 7h 40m

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

Southwest Airlines flies from Chicago Midway International Airport (MDW) to Oakland International Airport (OAK) every 4 hours. Alternatively, you can take a bus from Chicago Bus Station to Paradise Cay via Denver Union Station, Sparks Transit Center, and Oakland in around 2d 2h.

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Need to know: Greyhound

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