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

Find Transport to Winchester

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

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

  1. Train, taxi via Springfield (Amtrak)

    best
    1. Take the train from Chicago Union Station to Springfieldtrain train Lincoln Service / ...
    2. Take the taxi from Ymca to Winchestertaxi taxi
    4h 59m
    $182–274

  2. Drive 248.9 mi

    cheapest
    1. Drive from Chicago to Winchestercar car 248.9 mi
    4h 18m
    $46–66

  3. Bus, taxi

    1. Take the bus from Chicago Bus Station to Springfield SMTD Transfer Centerbus bus FlixBus 2510 / ...
    2. Take the taxi from Springfield SMTD Transfer Center to Winchestertaxi taxi
    5h 4m
    $176–230

  4. Fly to Abraham Lincoln Capital Airport, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Abraham Lincoln Capital Airport (SPI)plane plane ORD - SPI
    2. Take the taxi from Abraham Lincoln Capital Airport (SPI) to Winchestertaxi taxi
    3h 52m
    $178–445

  5. Train, taxi (Amtrak)

    1. Take the train from Chicago Union Station to Carlinville Stationtrain train Texas Eagle / ...
    2. Take the taxi from Carlinville Station to Winchestertaxi taxi
    5h 9m
    $193–298

  6. Fly to Quincy Regional Airport, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Quincy Regional Airport (UIN)plane plane ORD - UIN
    2. Take the taxi from Quincy Regional Airport (UIN) to Winchestertaxi taxi
    4h 21m
    $178–285

Chicago O'Hare International Airport (ORD) to Abraham Lincoln Capital Airport (SPI) flights

Calendar14Weekly Planes
Duration1h 7mAverage Duration
Ticket$38Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Winchester.ExpandLaunch map view
  • Distance: 239.8 mi
  • Duration: 4h 59m

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

There is no direct connection from Chicago to Winchester. However, you can take the train to Springfield, walk to Jefferson & 4th, take the line 7 bus to Ymca, then take the taxi to Winchester. Alternatively, you can take the bus to Springfield SMTD Transfer Center then take the taxi to Winchester.

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