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How to get fromOakland–Jack London Square Station to Chicagoby plane, bus (Greyhound), train (Amtrak), car, subway, or train

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There are 9 ways to get from Oakland–Jack London Square Station 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 14m
    $136–611

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

    cheapest
    1. Take the subway from Lake Merritt 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 50m
    $122–507

  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 2h
    $332–658

  4. Train (Amtrak)

    1. Take the train from Emeryville to Chicago Union Stationtrain train California Zephyr
    2d 5h
    $751–1,603

  5. Drive 2,120.7 mi

    1. Drive from Oakland–Jack London Square Station to Chicagocar car 2,120.7 mi
    32h 48m
    $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 44m
    $183–458

  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
    7h 8m
    $133–298

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

    1. Take the subway from Lake Merritt 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 21m
    $142–617

  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
    $172–668

Oakland–Jack London Square Station to Chicago by foot, subway, and bus (Greyhound)

Calendar7Weekly Services
Duration2d 2hAverage Duration
Ticket$332Cheapest Price
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Questions & Answers

Map of how to get from Oakland–Jack London Square Station to Chicago.ExpandLaunch map view
  • Distance: 1,859.8 mi
  • Duration: 6h 14m

What companies run services between Oakland–Jack London Square Station, 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 vehicle from Oakland–Jack London Square Station to Chicago Bus Station via Lake Merritt, West Oakland, Oakland, Sparks Transit Center, and Denver Union Station in around 2d 2h.

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Train operators
Bus operators

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