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How to get fromChicago to Drakesboroby plane, taxi, bus, train, or car

Find Transport to Drakesboro

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There are 10 ways to get from Chicago to Drakesboro 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 Chicago O'Hare International Airport to Owensboro–Daviess County Regional Airport, taxi

    best
    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 Drakesborotaxi taxi
    4h 18m
    $178–335

  2. Drive  358.6 mi

    cheapest
    1. Drive from Chicago to Drakesborocar car 358.6 mi
    7h 35m
    $66–95

  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 Evansville, INbus bus
    3. Take the bus from Evansville Bus Station to Madisonvillebus bus
    4. Take the taxi from Madisonville to Drakesborotaxi taxi
    11h 16m
    $156–336

  4. Train, bus, taxi

    1. Take the train from Chicago Union Station to Carbondaletrain train
    2. Take the bus from Carbondale Intermodal Station to Clarksville Park & Ridebus bus
    3. Take the bus from Clarksville Park & Ride to Madisonvillebus bus
    4. Take the taxi from Madisonville to Drakesborotaxi taxi
    12h 11m
    $266–393

  5. Fly Chicago O'Hare International Airport to Evansville, bus, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Evansville (EVV)plane plane ORD - EVV
    2. Take the bus from Evansville Bus Station to Madisonvillebus bus
    3. Take the taxi from Madisonville to Drakesborotaxi taxi
    5h 58m
    $126–389

  6. Fly Chicago Midway International Airport to Nashville, bus, taxi

    1. Fly from Chicago Midway International Airport (MDW) to Nashville (BNA)plane plane MDW - BNA
    2. Take the bus from Nashville Bus Station to Madisonvillebus bus
    3. Take the taxi from Madisonville to Drakesborotaxi taxi
    7h 9m
    $156–588

  7. Fly Chicago O'Hare International Airport to Nashville, bus, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Nashville (BNA)plane plane ORD - BNA
    2. Take the bus from Nashville Bus Station to Madisonvillebus bus
    3. Take the taxi from Madisonville to Drakesborotaxi taxi
    7h 30m
    $182–368

  8. Train, bus, taxi via St. Louis

    1. Take the train from Chicago Union Station to St. Louistrain train
    2. Take the bus from St Louis Bus Station to Madisonvillebus bus
    3. Take the taxi from Madisonville to Drakesborotaxi taxi
    11h 17m
    $251–374

  9. Bus, taxi via Bloomington

    1. Take the bus from Chicago Bus Station to Bloomingtonbus bus
    2. Take the bus from Bloomington, IN to Evansville, INbus bus
    3. Take the bus from Evansville Bus Station to Madisonvillebus bus
    4. Take the taxi from Madisonville to Drakesborotaxi taxi
    12h 1m
    $145–293

  10. Train, bus, taxi via Indianapolis

    1. Take the train from Chicago Union Station to Indianapolistrain train
    2. Take the bus from Indianapolis Union Station to Evansville, INbus bus
    3. Take the bus from Evansville Bus Station to Madisonvillebus bus
    4. Take the taxi from Madisonville to Drakesborotaxi taxi
    13h 5m
    $232–455

Chicago O'Hare International Airport (ORD) to Owensboro–Daviess County Regional Airport (OWB) flights

Calendar7Weekly Planes
Duration1h 35mAverage Duration
Ticket$40Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Drakesboro.ExpandLaunch map view
  • Distance: 355.7 mi
  • Duration: 4h 18m

What companies run services between Chicago, IL, USA and Drakesboro, KY, USA?

There is no direct connection from Chicago to Drakesboro. However, you can take the subway to O'Hare, walk to Chicago O'Hare International Airport (ORD) airport, fly to Owensboro–Daviess County Regional Airport (OWB), then take the taxi to Drakesboro. Alternatively, you can take the bus to Indianapolis Union Station, take the bus to Evansville, IN, take the bus to Madisonville, then take the taxi to Drakesboro.

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