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How to get fromChicago Union Station to Kentucky Derbyby subway, plane, bus (Greyhound, Amtrak), train, bus, car, or bus (Amtrak)

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There are 7 ways to get from Chicago Union Station to Kentucky Derby by subway, plane, bus (Greyhound, Amtrak), train, bus, car, or bus (Amtrak)

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Subway to Chicago Midway International Airport, fly to Louisville International Airport

    best
    1. Take the subway from Quincy to Midwaysubway subway
    2. Fly from Chicago Midway International Airport (MDW) to Louisville International Airport (SDF)plane plane MDW - SDF
    4h 27m
    $84–558

  2. Bus via Indianapolis

    cheapest
    1. Take the bus from Chicago Bus Station to Indianapolis Union Stationbus bus Greyhound US0100 / ...
    2. Take the bus from Indianapolis Union Station to Louisville, KYbus bus Chicago
    8h 10m
    $50–100

  3. Train, bus (Amtrak)

    1. Take the train from Chicago Union Station to Indianapolistrain train Cardinal
    2. Take the bus from Indianapolis Union Station to Louisville, KYbus bus Chicago
    9h 50m
    $86–177

  4. Drive 298.8 mi

    1. Drive from Chicago Union Station to Kentucky Derbycar car 298.8 mi
    5h 10m
    $55–79

  5. Fly Chicago O'Hare International Airport to Louisville International Airport

    1. Fly from Chicago O'Hare International Airport (ORD) to Louisville International Airport (SDF)plane plane ORD - SDF
    4h 58m
    $68–428

  6. Fly Chicago O'Hare International Airport to Blue Grass Airport, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to Blue Grass Airport (LEX)plane plane ORD - LEX
    2. Drive from Lexington-Airport-LEX to Kentucky Derbycar car
    4h 54m
    $116–675

  7. Bus (Amtrak)

    1. Take the bus from Chicago Union Station to Louisville, KYbus bus Chicago
    8h 31m
    $51–59

Chicago Union Station to Kentucky Derby by foot and bus

Calendar14Weekly Services
Duration8h 10mAverage Duration
Ticket$50Cheapest Price
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Questions & Answers

Map of how to get from Chicago Union Station to Kentucky Derby.ExpandLaunch map view
  • Distance: 288.4 mi
  • Duration: 4h 27m

What companies run services between Chicago Union Station, IL, USA and Kentucky Derby, KY, USA?

You can take a vehicle from Chicago Union Station to Kentucky Derby via Chicago Bus Station, Indianapolis Union Station, Louisville, KY, W Broadway @ S 11th, Eastern Parkway @ Bardstown, and Taylor @ Larchmont in around 8h 10m. Alternatively, American Airlines and United Airlines fly from Chicago O'Hare International Airport (ORD) to Louisville International Airport (SDF) every 3 hours.

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