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How to get fromCharlestown to Chicagoby plane, bus (Amtrak), bus, train, car, or bus (Greyhound)

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There are 7 ways to get from Charlestown to Chicago by plane, bus (Amtrak), bus, train, car, or bus (Greyhound)

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 Louisville International Airport to Chicago Midway International Airport

    best
    1. Fly from Louisville International Airport (SDF) to Chicago Midway International Airport (MDW)plane plane SDF - MDW
    2h 24m
    $111–425

  2. Drive 282.7 mi

    cheapest
    1. Drive from Charlestown to Chicagocar car 282.7 mi
    4h 55m
    $52–75

  3. Bus (Amtrak)

    1. Take the bus from Louisville, KY to Chicago Union Stationbus bus
    6h 28m
    $98–116

  4. Bus, train (Amtrak)

    1. Take the bus from Louisville, KY to Indianapolis Union Stationbus bus
    2. Take the train from Indianapolis to Chicago Union Stationtrain train Cardinal
    8h 48m
    $130–231

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

    1. Fly from Louisville International Airport (SDF) to Chicago O'Hare International Airport (ORD)plane plane SDF - ORD
    2h 56m
    $106–375

  6. Drive to Blue Grass Airport, fly to Chicago O'Hare International Airport

    1. Drive from Charlestown to Lexington-Airport-LEXcar car
    2. Fly from Blue Grass Airport (LEX) to Chicago O'Hare International Airport (ORD)plane plane LEX - ORD
    4h
    $77–416

  7. Bus via Speedway

    1. Take the bus from El Mercadito Grocery - Clarksville, IN to Indianapolisbus bus Memphis
    2. Take the bus from Indianapolis Union Station to Chicago Bus Stationbus bus Greyhound US0100 / ...
    8h 16m
    $108–244

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

Calendar20Weekly Planes
Duration1h 15mAverage Duration
Ticket$54Cheapest Price
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Questions & Answers

Map of how to get from Charlestown to Chicago.ExpandLaunch map view
  • Distance: 302.5 mi
  • Duration: 2h 24m

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

Southwest Airlines flies from Louisville International Airport (SDF) to Chicago Midway International Airport (MDW) 3 times a day. Alternatively, Amtrak Thruway operates a bus from Louisville, KY to Chicago Union Station twice daily. Tickets cost $50–60 and the journey takes 6h.

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