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

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There are 8 ways to get from Chicago to Pleasanton by plane, 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 57m
    $258–1,214

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

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to San Francisco International Airport (SFO)plane plane ORD - SFO
    2. Take the subway from Embarcadero to Dublin / Pleasantonsubway subway
    8h 3m
    $102–415

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Richmondtrain train California Zephyr
    2d 6h
    $706–1,509

  4. Drive 2,130.1 mi

    1. Drive from Chicago to Pleasantoncar car 2,130.1 mi
    32h 57m
    $389–562

  5. 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 Embarcadero to Dublin / Pleasantonsubway subway
    7h 40m
    $136–625

  6. 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 20m
    $302–1,418

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

    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 56m
    $212–968

  8. 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 4m
    $304–1,376

Chicago to Pleasanton by train and subway (Amtrak)

Calendar7Weekly Services
Duration2d 6hAverage Duration
Ticket$706Cheapest Price
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Questions & Answers

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) every 4 hours. Alternatively, Amtrak operates a train from Chicago Union Station to Richmond once daily. Tickets cost $700–1,500 and the journey takes 2d 4h.

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