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How to get fromMadison to Winchesterby car, plane, taxi, or bus

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There are 6 ways to get from Madison to Winchester by car, plane, taxi, or bus

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 518.9 mi

    best
    1. Drive from Madison to Winchestercar car 518.9 mi
    9h 7m
    $95–137

  2. Fly Dane County Regional Airport-Truax Field to Blue Grass Airport, taxi

    1. Fly from Dane County Regional Airport-Truax Field (MSN) to Blue Grass Airport (LEX)plane plane MSN - LEX
    2. Take the taxi from Lexington-Airport-LEX to Winchestertaxi taxi
    6h 2m
    $242–1,102

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

    1. Take the bus from 250 N. Lake St - Madison UW Campus to O'Hare International Airport - Terminal 1 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
    6h 2m
    $204–800

  4. Fly Dane County Regional Airport-Truax Field to Covington, drive

    1. Fly from Dane County Regional Airport-Truax Field (MSN) to Covington (CVG)plane plane MSN - CVG
    2. Drive from Covington (CVG) to Winchestercar car
    6h 33m
    $128–727

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

    1. Take the bus from 250 N. Lake St - Madison UW Campus to O'Hare International Airport - Terminal 1 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
    6h 56m
    $190–925

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

    1. Take the bus from 250 N. Lake St - Madison UW Campus to O'Hare International Airport - Terminal 1 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
    7h 4m
    $105–495

Dane County Regional Airport-Truax Field (MSN) to Blue Grass Airport (LEX) flights

Calendar83Weekly Planes
Duration5h 38mAverage Duration
Ticket$167Cheapest Price
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Questions & Answers

Map of how to get from Madison to Winchester.ExpandLaunch map view
  • Distance: 518.9 mi
  • Duration: 9h 7m

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

You can drive from Madison to Winchester in around 9h 7m.

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