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

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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 25m
    $284–984

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

    cheapest
    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
    7h 57m
    $174–341

  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
    $448–802

  4. Train (Amtrak)

    1. Take the train from Chicago Union Station to Richmondtrain train California Zephyr
    2d 5h
    $844–1,649

  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 Midway International Airport to San Francisco International Airport, bus

    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 37m
    $254–501

  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 33m
    $268–940

  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 5m
    $228–640

  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 15m
    $294–1,034

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

Calendar33Weekly Planes
Duration6hAverage Duration
Ticket$220Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Paradise Cay.ExpandLaunch map view
  • Distance: 1,886.8 mi
  • Duration: 7h 25m

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) 5 times a day. 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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