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How to get fromWinchester to Chicagoby bus, taxi, train, car, or plane

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There are 7 ways to get from Winchester to Chicago by bus, taxi, train, 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. Bus

    best
    1. Take the bus from Portland, IN to Chicagobus bus Columbus-Chicago
    5h 41m
    $30–70

  2. Taxi, train (Amtrak)

    1. Take the taxi from Winchester to Connersville Stationtaxi taxi
    2. Take the train from Connersville Station to Chicago Union Stationtrain train Cardinal
    8h 18m
    $89–180

  3. Drive 224.3 mi

    1. Drive from Winchester to Chicagocar car 224.3 mi
    4h 53m
    $41–60

  4. Taxi to Dayton, fly to Chicago O'Hare International Airport

    1. Take the taxi from Winchester to Dayton-Airport-DAYtaxi taxi
    2. Fly from Dayton (DAY) to Chicago O'Hare International Airport (ORD)plane plane DAY - ORD
    3h 31m
    $182–509

  5. Bus to Fort Wayne International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Portland, IN to Fort Wayne, INbus bus
    2. Fly from Fort Wayne International Airport (FWA) to Chicago O'Hare International Airport (ORD)plane plane FWA - ORD
    4h 43m
    $70–315

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

    1. Take the bus from Muncie Ball State Univ, IN to Indianapolis Airportbus bus
    2. Fly from Indianapolis (IND) to Chicago O'Hare International Airport (ORD)plane plane IND - ORD
    5h 38m
    $456–1,155

  7. Bus to Indianapolis, fly to Chicago Midway International Airport

    1. Take the bus from Muncie Ball State Univ, IN to Indianapolis Airportbus bus
    2. Fly from Indianapolis (IND) to Chicago Midway International Airport (MDW)plane plane IND - MDW
    5h 14m
    $81–385

Dayton (DAY) to Chicago O'Hare International Airport (ORD) flights

Calendar55Weekly Planes
Duration1h 33mAverage Duration
Ticket$52Cheapest Price
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Questions & Answers

Map of how to get from Winchester to Chicago.ExpandLaunch map view
  • Distance: 238.1 mi
  • Duration: 5h 41m

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

Barons Bus operates a bus from Portland, IN to Chicago once daily. Tickets cost $21–60 and the journey takes 5h 15m.

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