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How to get fromChicago Midway Airport (MDW) to Oaklandby plane, train (Amtrak), bus (Flixbus, Greyhound), subway, train, or car

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There are 8 ways to get from Chicago Midway Airport (MDW) to Oakland by plane, train (Amtrak), bus (Flixbus, Greyhound), subway, train, or car

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
    4h 59m
    $192–792

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

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to San Francisco International Airport (SFO)plane plane ORD - SFO
    7h 41m
    $136–304

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Emeryvilletrain train California Zephyr
    2d 6h
    $706–1,608

  4. Bus

    1. Take the bus from Chicago Midway Airport to Illinois Terminalbus bus
    2. Take the bus from Champaign Intermodal Trans Ctr to St Louis Bus Stationbus bus
    3. Take the bus from St Louis Bus Station to Los Angeles Union Stationbus bus
    4. Take the bus from Los Angeles Union Station to Oaklandbus bus
    2d 8h
    $407–765

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

    1. Fly from Chicago Midway International Airport (MDW) to San Francisco International Airport (SFO)plane plane MDW - SFO
    5h 18m
    $182–447

  6. Fly Chicago Midway International Airport to Norman Y. Mineta San José International Airport, BART

    1. Fly from Chicago Midway International Airport (MDW) to Norman Y. Mineta San José International Airport (SJC)plane plane MDW - SJC
    2. Take the subway from Milpitas to 12th Street / Oakland City Centersubway subway
    6h 8m
    $191–769

  7. 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
    7h 44m
    $217–854

  8. Drive 2,114.4 mi

    1. Drive from Chicago Midway Airport (MDW) to Oaklandcar car 2,114.4 mi
    32h 51m
    $386–558

Chicago Midway Airport (MDW) to Oakland by subway, bus, and train (Amtrak)

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

Map of how to get from Chicago Midway Airport (MDW) to Oakland.ExpandLaunch map view
  • Distance: 1,849 mi
  • Duration: 4h 59m

What companies run services between Chicago Midway Airport (MDW), USA and Oakland, 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 Emeryville once daily. Tickets cost $700–1,600 and the journey takes 2d 4h.

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