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

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There are 9 ways to get from Chicago to Oakland by plane, bus (Greyhound), train (Amtrak), car, 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
    6h 35m
    $226–962

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

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to San Francisco International Airport (SFO)plane plane ORD - SFO
    7h 12m
    $134–299

  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 1h
    $349–669

  4. Train (Amtrak)

    1. Take the train from Chicago Union Station to Emeryvilletrain train California Zephyr
    2d 4h
    $750–1,600

  5. Drive 2,119.3 mi

    1. Drive from Chicago to Oaklandcar car 2,119.3 mi
    32h 45m
    $387–559

  6. Fly Chicago Midway International Airport to San Francisco International Airport

    1. Fly from Chicago Midway International Airport (MDW) to San Francisco International Airport (SFO)plane plane MDW - SFO
    6h 52m
    $214–459

  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 12th Street / Oakland City Centersubway subway
    7h 44m
    $222–918

  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 12th Street / Oakland City Centersubway subway
    8h 15m
    $172–568

  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 Oaklandtrain train
    9h 18m
    $244–969

Chicago to Oakland by bus (Greyhound)

Calendar7Weekly Buses
Duration2d 1hAverage Duration
Ticket$349Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Oakland.ExpandLaunch map view
  • Distance: 1,860.1 mi
  • Duration: 6h 35m

What companies run services between Chicago, IL, USA and Oakland, 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 Oakland via Denver Union Station and Sparks Transit Center in around 2d 1h.

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