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

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There are 9 ways to get from Oakland to Chicago 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 Oakland International Airport to Chicago Midway International Airport

    best
    1. Fly from Oakland International Airport (OAK) to Chicago Midway International Airport (MDW)plane plane OAK - MDW
    6h 4m
    $147–661

  2. BART to Norman Y. Mineta San José International Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the subway from 12th Street / Oakland City Center to Milpitassubway subway
    2. Fly from Norman Y. Mineta San José International Airport (SJC) to Chicago O'Hare International Airport (ORD)plane plane SJC - ORD
    7h 39m
    $132–567

  3. Bus (Greyhound)

    1. Take the bus from Oakland to Sparks Transit Centerbus bus
    2. Take the bus from Sparks Transit Center to Denver Union Stationbus bus
    3. Take the bus from Denver Union Station to Chicago Bus Stationbus bus
    2d 1h
    $344–674

  4. Train (Amtrak)

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

  5. Drive 2,119.7 mi

    1. Drive from Oakland to Chicagocar car 2,119.7 mi
    32h 47m
    $387–559

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

    1. Fly from San Francisco International Airport (SFO) to Chicago Midway International Airport (MDW)plane plane SFO - MDW
    6h 27m
    $213–458

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

    1. Fly from San Francisco International Airport (SFO) to Chicago O'Hare International Airport (ORD)plane plane SFO - ORD
    6h 51m
    $133–298

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

    1. Take the subway from 12th Street / Oakland City Center to Milpitassubway subway
    2. Fly from Norman Y. Mineta San José International Airport (SJC) to Chicago Midway International Airport (MDW)plane plane SJC - MDW
    7h 12m
    $152–617

  9. Train to Sacramento International Airport, fly to Chicago Midway International Airport

    1. Take the train from Oakland to Sacramentotrain train
    2. Fly from Sacramento International Airport (SMF) to Chicago Midway International Airport (MDW)plane plane SMF - MDW
    8h 32m
    $184–717

Oakland to Chicago by bus (Greyhound)

Calendar7Weekly Buses
Duration2d 1hAverage Duration
Ticket$344Cheapest Price
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Questions & Answers

Map of how to get from Oakland to Chicago.ExpandLaunch map view
  • Distance: 1,860 mi
  • Duration: 6h 4m

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

Southwest Airlines flies from Oakland International Airport (OAK) to Chicago Midway International Airport (MDW) 5 times a day. Alternatively, you can take a bus from Oakland to Chicago Bus Station via Sparks Transit Center and Denver Union Station in around 2d 1h.

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