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How to get fromWinchester to Chicagoby plane or car

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There are 6 ways to get from Winchester to Chicago by plane 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 Blue Grass Airport to Chicago O'Hare International Airport

    best
    1. Fly from Blue Grass Airport (LEX) to Chicago O'Hare International Airport (ORD)plane plane LEX - ORD
    3h 7m
    $136–482

  2. Drive to Louisville International Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Drive from Winchester to Louisville-Airport-SDFcar car
    2. Fly from Louisville International Airport (SDF) to Chicago O'Hare International Airport (ORD)plane plane SDF - ORD
    3h 59m
    $64–329

  3. Drive 373.8 mi

    1. Drive from Winchester to Chicagocar car 373.8 mi
    6h 38m
    $69–99

  4. Drive to Louisville International Airport, fly to Chicago Midway International Airport

    1. Drive from Winchester to Louisville-Airport-SDFcar car
    2. Fly from Louisville International Airport (SDF) to Chicago Midway International Airport (MDW)plane plane SDF - MDW
    3h 27m
    $69–379

  5. Drive to Covington, fly to Chicago Midway International Airport

    1. Drive from Winchester to Covington (CVG)car car
    2. Fly from Covington (CVG) to Chicago Midway International Airport (MDW)plane plane CVG - MDW
    3h 22m
    $169–389

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

    1. Drive from Winchester to Covington (CVG)car car
    2. Fly from Covington (CVG) to Chicago O'Hare International Airport (ORD)plane plane CVG - ORD
    3h 50m
    $169–879

Blue Grass Airport (LEX) to Chicago O'Hare International Airport (ORD) flights

Calendar56Weekly Planes
Duration2h 7mAverage Duration
Ticket$62Cheapest Price
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Questions & Answers

Map of how to get from Winchester to Chicago.ExpandLaunch map view
  • Distance: 366 mi
  • Duration: 3h 7m

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

American Airlines, United Airlines, and Delta fly from Blue Grass Airport (LEX) to Chicago O'Hare International Airport (ORD) every 4 hours.

Airlines

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