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

Find Transport to Pleasanton

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There are 9 ways to get from Chicago to Pleasanton by plane, bus, subway, train (Amtrak), car, 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 6m
    $168–764

  2. Fly Chicago O'Hare International Airport to Norman Y. Mineta San José International Airport, train

    cheapest
    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 train from Santa Clara Station to Pleasanton Stationtrain train
    8h 45m
    $122–518

  3. Bus, BART

    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 subway from West Oakland to Dublin / Pleasantonsubway subway
    2d 3h
    $401–615

  4. Train (Amtrak)

    1. Take the train from Chicago Union Station to Richmondtrain train California Zephyr
    2d 6h
    $1,329–2,039

  5. Drive  2,130.1 mi

    1. Drive from Chicago to Pleasantoncar car 2,130.1 mi
    32h 58m
    $389–562

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

    1. Fly from Chicago O'Hare International Airport (ORD) to San Francisco International Airport (SFO)plane plane ORD - SFO
    2. Take the subway from Daly City to Dublin / Pleasantonsubway subway
    7h 58m
    $188–297

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

    1. Fly from Chicago Midway International Airport (MDW) to San Francisco International Airport (SFO)plane plane MDW - SFO
    2. Take the subway from Daly City to Dublin / Pleasantonsubway subway
    7h 53m
    $188–437

  8. Fly Chicago Midway International Airport to Norman Y. Mineta San José International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Norman Y. Mineta San José International Airport (SJC)plane plane MDW - SJC
    2. Take the train from Santa Clara Station to Pleasanton Stationtrain train
    8h 23m
    $182–768

  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
    10h 26m
    $234–896

Chicago to Pleasanton by bus and subway

Calendar7Weekly Services
Duration2d 3hAverage Duration
Ticket$401Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Pleasanton.ExpandLaunch map view
  • Distance: 1,872.9 mi
  • Duration: 7h 6m

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

Southwest Airlines flies from Chicago Midway International Airport (MDW) to Oakland International Airport (OAK) 5 times a day. Alternatively, Amtrak operates a train from Chicago Union Station to Richmond once daily. Tickets cost $1,300–2,100 and the journey takes 2d 4h.

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Train operators
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