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

Find Transport to Winchester

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There are 7 ways to get from Chicago to Winchester by plane, taxi, bus, car, 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. Fly Chicago O'Hare International Airport to Huntsville International Airport-Carl T Jones Field, taxi

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Huntsville International Airport-Carl T Jones Field (HSV)plane plane ORD - HSV
    2. Take the taxi from Huntsville International Airport-Carl T Jones Field (HSV) to Winchestertaxi taxi
    4h 49m
    $208–595

  2. Drive 518.5 mi

    cheapest
    1. Drive from Chicago to Winchestercar car 518.5 mi
    10h 5m
    $95–137

  3. Bus, taxi (Greyhound)

    1. Take the bus from Chicago Train Station to Manchesterbus bus Greyhound US0100
    2. Take the taxi from Manchester to Winchestertaxi taxi
    13h 19m
    $135–221

  4. Fly Chicago O'Hare International Airport to Chattanooga Metropolitan Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Chattanooga Metropolitan Airport (CHA)plane plane ORD - CHA
    2. Take the bus from Groome Transportation Chattanooga to Monteaglebus bus
    5h 51m
    $210–775

  5. Fly Chicago Midway International Airport to Nashville, bus

    1. Fly from Chicago Midway International Airport (MDW) to Nashville (BNA)plane plane MDW - BNA
    2. Take the bus from Nashville Airport to Monteaglebus bus
    5h 40m
    $158–550

  6. Fly Chicago O'Hare International Airport to Nashville, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Nashville (BNA)plane plane ORD - BNA
    2. Take the bus from Nashville Airport to Monteaglebus bus
    6h 2m
    $188–400

  7. Train, bus, taxi

    1. Take the train from Chicago Union Station to Carbondaletrain train
    2. Take the bus from Carbondale Intermodal Station to Nashville Bus Stationbus bus
    3. Take the bus from Nashville Bus Station to Manchesterbus bus
    4. Take the taxi from Manchester to Winchestertaxi taxi
    13h 49m
    $191–346

Chicago O'Hare International Airport (ORD) to Huntsville International Airport-Carl T Jones Field (HSV) flights

Calendar39Weekly Planes
Duration2h 39mAverage Duration
Ticket$77Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Winchester.ExpandLaunch map view
  • Distance: 585.6 mi
  • Duration: 4h 49m

What companies run services between Chicago, IL, USA and Winchester, Franklin County, TN, 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 Huntsville International Airport-Carl T Jones Field (HSV), then take the taxi to Winchester. Alternatively, you can take the bus to Manchester then take the taxi to Winchester.

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