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How to get fromOakland to Chicago Midway Airport (MDW)by plane, train (Amtrak), bus (Greyhound, Flixbus), subway, train, or car

Find Transport to Chicago Midway Airport (MDW)

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There are 9 ways to get from Oakland to Chicago Midway Airport (MDW) by plane, train (Amtrak), bus (Greyhound, Flixbus), 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 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
    5h 23m
    $135–606

  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
    8h 9m
    $124–512

  3. 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 19m
    $135–303

  4. Train (Amtrak)

    1. Take the train from Emeryville to Chicago Union Stationtrain train California Zephyr
    2d 4h
    $743–1,557

  5. Bus

    1. Take the bus from Oakland to Los Angeles Union Stationbus bus
    2. Take the bus from Los Angeles Union Station to St Louis Bus Stationbus bus
    3. Take the bus from St Louis Bus Station to Chicagobus bus
    2d 10h
    $388–745

  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
    5h 45m
    $181–453

  7. 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
    6h 30m
    $140–612

  8. 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
    7h 50m
    $169–662

  9. Drive 2,114.2 mi

    1. Drive from Oakland to Chicago Midway Airport (MDW)car car 2,114.2 mi
    32h 49m
    $386–558

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

Calendar7Weekly Services
Duration2d 4hAverage Duration
Ticket$743Cheapest Price
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Questions & Answers

Map of how to get from Oakland to Chicago Midway Airport (MDW).ExpandLaunch map view
  • Distance: 1,849 mi
  • Duration: 5h 23m

What companies run services between Oakland, CA, USA and Chicago Midway Airport (MDW), USA?

Southwest Airlines flies from Oakland International Airport (OAK) to Chicago Midway International Airport (MDW) 5 times a day. Alternatively, Amtrak operates a train from Emeryville to Chicago Union Station once daily. Tickets cost $700–1,600 and the journey takes 2d 4h.

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