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

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There are 8 ways to get from Chicago to Kentucky Derby by subway, plane, bus (Greyhound, Flixbus), 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 Adams/Wabash to Midwaysubway subway
    2. Fly from Chicago Midway International Airport (MDW) to Louisville International Airport (SDF)plane plane MDW - SDF
    4h 12m
    $88–608

  2. Bus

    cheapest
    1. Take the bus from Chicago Bus Station to Louisville Bus Stationbus bus Greyhound US0100
    7h 41m
    $43–82

  3. Train, bus via Indianapolis

    1. Take the train from Chicago Union Station to Indianapolistrain train Cardinal
    2. Take the bus from Indianapolis Union Station to Louisville Bus Stationbus bus Greyhound US0100 / ...
    9h 20m
    $75–163

  4. Drive  298 mi

    1. Drive from Chicago to Kentucky Derbycar car 298 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 42m
    $68–448

  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 41m
    $56–315

  7. Train, bus

    1. Take the train from Van Buren St. to Gary Metro Centertrain train Ssl / ...
    2. Take the bus from Gary Bus Station to Louisville Bus Stationbus bus Greyhound US0100
    8h 42m
    $44–86

  8. Bus via Lafayette (Amtrak)

    1. Take the bus from Chicago Union Station to Lafayette Amtrak Stationbus bus Chicago
    2. Take the bus from Lafayette Amtrak Station to Louisville, KYbus bus Chicago
    9h 56m
    $55–97

Chicago Midway International Airport (MDW) to Louisville International Airport (SDF) flights

Calendar21Weekly Planes
Duration1h 28mAverage Duration
Ticket$89Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Kentucky Derby.ExpandLaunch map view
  • Distance: 286.7 mi
  • Duration: 4h 12m

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

Greyhound USA operates a bus from Chicago Bus Station to Louisville Bus Station 4 times a day. Tickets cost $40–80 and the journey takes 6h 5m. Flixbus USA also services this route twice daily. Alternatively, American Airlines and United Airlines fly from Chicago O'Hare International Airport (ORD) to Louisville International Airport (SDF) hourly.

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