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How to get fromChicago to Oakland Cityby plane, taxi, bus, train, or car

Find Transport to Oakland City

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There are 6 ways to get from Chicago to Oakland City by plane, taxi, bus, 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 to Evansville, taxi

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Evansville (EVV)plane plane ORD - EVV
    2. Take the taxi from Evansville (EVV) to Oakland Citytaxi taxi
    3h 36m
    $92–335

  2. Drive  264.3 mi

    cheapest
    1. Drive from Chicago to Oakland Citycar car 264.3 mi
    5h 47m
    $47–68

  3. Bus, taxi

    1. Take the bus from Chicago Bus Station to Indianapolis Union Stationbus bus
    2. Take the bus from Indianapolis Union Station to Dale, IN - Denny'sbus bus
    3. Take the taxi from Dale, IN to Oakland Citytaxi taxi
    8h 18m
    $143–289

  4. Train, bus, taxi

    1. Take the train from Chicago Union Station to Indianapolistrain train
    2. Take the bus from Indianapolis Union Station to Dale, IN - Denny'sbus bus
    3. Take the taxi from Dale, IN to Oakland Citytaxi taxi
    10h 7m
    $218–405

  5. Fly to Owensboro–Daviess County Regional Airport, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Owensboro–Daviess County Regional Airport (OWB)plane plane ORD - OWB
    2. Take the taxi from Owensboro–Daviess County Regional Airport (OWB) to Oakland Citytaxi taxi
    4h 59m
    $162–415

  6. Bus, taxi via Bloomington

    1. Take the bus from Chicago Bus Station to Bloomingtonbus bus
    2. Take the bus from Bloomington, IN to Dale, IN - Denny'sbus bus
    3. Take the taxi from Dale, IN to Oakland Citytaxi taxi
    9h 3m
    $133–235

Chicago O'Hare International Airport (ORD) to Evansville (EVV) flights

Calendar14Weekly Planes
Duration1h 26mAverage Duration
Ticket$39Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Oakland City.ExpandLaunch map view
  • Distance: 315.5 mi
  • Duration: 3h 36m

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

There is no direct connection from Chicago to Oakland City. However, you can take the subway to O'Hare, walk to Chicago O'Hare International Airport (ORD) airport, fly to Evansville (EVV), then take the taxi to Oakland City. Alternatively, you can take the bus to Indianapolis Union Station, take the bus to Dale, IN - Denny's, then take the taxi to Oakland City.

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