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How to get fromMilwaukee to Winchesterby car, plane, taxi, bus, or train

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There are 7 ways to get from Milwaukee to Winchester by car, plane, taxi, bus, or train

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

  1. Drive 461.2 mi

    best
    1. Drive from Milwaukee to Winchestercar car 461.2 mi
    8h 18m
    $85–122

  2. Fly General Mitchell International Airport to Blue Grass Airport, taxi

    1. Fly from General Mitchell International Airport (MKE) to Blue Grass Airport (LEX)plane plane MKE - LEX
    2. Take the taxi from Lexington-Airport-LEX to Winchestertaxi taxi
    5h 37m
    $242–1,052

  3. Bus to Chicago O'Hare International Airport, fly to Blue Grass Airport, taxi

    1. Take the bus from Milwaukee Intermodal/Amtrak Station to O'Hare International Airport - Terminal 2 Departuresbus bus
    2. Fly from Chicago O'Hare International Airport (ORD) to Blue Grass Airport (LEX)plane plane ORD - LEX
    3. Take the taxi from Lexington-Airport-LEX to Winchestertaxi taxi
    4h 52m
    $218–791

  4. Bus to Chicago O'Hare International Airport, fly to Covington, drive

    1. Take the bus from Milwaukee Intermodal/Amtrak Station to O'Hare International Airport - Terminal 2 Departuresbus bus
    2. Fly from Chicago O'Hare International Airport (ORD) to Covington (CVG)plane plane ORD - CVG
    3. Drive from Covington (CVG) to Winchestercar car
    5h 46m
    $204–916

  5. Bus to Chicago O'Hare International Airport, fly to Louisville International Airport, drive

    1. Take the bus from Milwaukee Intermodal/Amtrak Station to O'Hare International Airport - Terminal 2 Departuresbus bus
    2. Fly from Chicago O'Hare International Airport (ORD) to Louisville International Airport (SDF)plane plane ORD - SDF
    3. Drive from Louisville-Airport-SDF to Winchestercar car
    5h 54m
    $119–486

  6. Train to Chicago Midway International Airport, fly to Louisville International Airport, drive

    1. Take the train from Milwaukee to Chicago Union Stationtrain train
    2. Fly from Chicago Midway International Airport (MDW) to Louisville International Airport (SDF)plane plane MDW - SDF
    3. Drive from Louisville-Airport-SDF to Winchestercar car
    6h 5m
    $128–639

  7. Train to Chicago Midway International Airport, fly to Covington, drive

    1. Take the train from Milwaukee to Chicago Union Stationtrain train
    2. Fly from Chicago Midway International Airport (MDW) to Covington (CVG)plane plane MDW - CVG
    3. Drive from Covington (CVG) to Winchestercar car
    6h 6m
    $198–449

General Mitchell International Airport (MKE) to Blue Grass Airport (LEX) flights

Calendar117Weekly Planes
Duration5h 9mAverage Duration
Ticket$160Cheapest Price
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Questions & Answers

Map of how to get from Milwaukee to Winchester.ExpandLaunch map view
  • Distance: 461.2 mi
  • Duration: 8h 18m

What companies run services between Milwaukee, WI, USA and Winchester, KY, USA?

You can drive from Milwaukee to Winchester in around 8h 18m.

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