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How to get fromPleasanton to Chicagoby plane, subway, bus, train (Amtrak), car or train

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There are 8 ways to get from Pleasanton to Chicago by plane, subway, bus, 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 Oakland International Airport to Chicago Midway International Airport

    best
    1. Fly from Oakland International Airport (OAK) to Chicago Midway International Airport (MDW)planeOAK - MDW
    6h 26m
    $157–663

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

    cheapest
    1. Take the subway from Dublin / Pleasanton to Daly Citysubway
    2. Fly from San Francisco International Airport (SFO) to Chicago O'Hare International Airport (ORD)planeSFO - ORD
    7h 26m
    $117–455

  3. BART, bus

    1. Take the subway from Dublin / Pleasanton to West Oaklandsubway
    2. Take the bus from Oakland to Sparks Transit Centerbus
    3. Take the bus from Sparks Transit Center to Denver Union Stationbus
    4. Take the bus from Denver Union Station to Chicago Bus Stationbus
    2d 3h
    $202–599

  4. Train (Amtrak)

    1. Take the train from Richmond to Chicago Union StationtrainCalifornia Zephyr
    2d 6h
    $176–1,609

  5. Drive 2,130.4 mi

    1. Drive from Pleasanton to Chicagocar2,130.4 mi
    32h 49m
    $389–562

  6. BART to San Francisco International Airport, fly to Chicago Midway International Airport

    1. Take the subway from Dublin / Pleasanton to Daly Citysubway
    2. Fly from San Francisco International Airport (SFO) to Chicago Midway International Airport (MDW)planeSFO - MDW
    7h 1m
    $147–625

  7. Train to Norman Y. Mineta San José International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Pleasanton Station to Santa Clara Stationtrain
    2. Fly from Norman Y. Mineta San José International Airport (SJC) to Chicago O'Hare International Airport (ORD)planeSJC - ORD
    7h 13m
    $145–621

  8. Train to Norman Y. Mineta San José International Airport, fly to Chicago Midway International Airport

    1. Take the train from Pleasanton Station to Santa Clara Stationtrain
    2. Fly from Norman Y. Mineta San José International Airport (SJC) to Chicago Midway International Airport (MDW)planeSJC - MDW
    7h 4m
    $195–821

Pleasanton to Chicago by bus and subway

Calendar7Weekly Services
Duration2d 3hAverage Duration
Ticket$202Cheapest Price
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Questions & Answers

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

Southwest Airlines flies from Oakland International Airport (OAK) to Chicago Midway International Airport (MDW) 4 times a day. Alternatively, Amtrak operates a train from Richmond to Chicago Union Station once daily. Tickets cost $170–1,600 and the journey takes 2d 4h.

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