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How to get fromChicago to Winchesterby plane, taxi, or car

Find Transport to Winchester

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There are 6 ways to get from Chicago to Winchester by plane, taxi, 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 Blue Grass Airport, taxi

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Blue Grass Airport (LEX)plane plane ORD - LEX
    2. Take the taxi from Lexington-Airport-LEX to Winchestertaxi taxi
    3h 48m
    $182–755

  2. Drive 372.3 mi

    cheapest
    1. Drive from Chicago to Winchestercar car 372.3 mi
    6h 38m
    $68–99

  3. Fly Chicago O'Hare International Airport to Covington, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to Covington (CVG)plane plane ORD - CVG
    2. Drive from Covington (CVG) to Winchestercar car
    4h 42m
    $168–880

  4. Fly Chicago Midway International Airport to Louisville International Airport, drive

    1. Fly from Chicago Midway International Airport (MDW) to Louisville International Airport (SDF)plane plane MDW - SDF
    2. Drive from Louisville-Airport-SDF to Winchestercar car
    4h 18m
    $98–580

  5. Fly Chicago Midway International Airport to Covington, drive

    1. Fly from Chicago Midway International Airport (MDW) to Covington (CVG)plane plane MDW - CVG
    2. Drive from Covington (CVG) to Winchestercar car
    4h 19m
    $168–390

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Louisville International Airport (SDF)plane plane ORD - SDF
    2. Drive from Louisville-Airport-SDF to Winchestercar car
    4h 50m
    $84–450

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

Calendar49Weekly Planes
Duration1h 34mAverage Duration
Ticket$101Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Winchester.ExpandLaunch map view
  • Distance: 368.8 mi
  • Duration: 3h 48m

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

There is no direct connection from Chicago to Winchester. However, you can take the subway to O'Hare, walk to Chicago O'Hare International Airport (ORD) airport, fly to Blue Grass Airport (LEX), then take the taxi to Winchester. Alternatively, you can drive from Chicago to Winchester in around 6h 38m.

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