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

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There are 7 ways to get from Chicago to Winchester by bus, train, taxi, 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 Chicago to Portland, INbus bus Chicago
    5h 51m
    $29–71

  2. Train, taxi

    1. Take the train from Chicago Union Station to Connersville Stationtrain train Cardinal
    2. Take the taxi from Connersville Station to Winchestertaxi taxi
    7h 45m
    $90–178

  3. Drive 224.3 mi

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

  4. Fly Chicago O'Hare International Airport to Dayton, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Dayton (DAY)plane plane ORD - DAY
    2. Take the taxi from Dayton-Airport-DAY to Winchestertaxi taxi
    4h 22m
    $172–455

  5. Fly Chicago O'Hare International Airport to Fort Wayne International Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Fort Wayne International Airport (FWA)plane plane ORD - FWA
    2. Take the bus from Fort Wayne, IN to Portland, INbus bus
    5h 45m
    $74–355

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Indianapolis (IND)plane plane ORD - IND
    2. Take the bus from Indianapolis Airport to Muncie, INbus bus
    6h 34m
    $456–1,156

  7. Fly Chicago Midway International Airport to Indianapolis, bus

    1. Fly from Chicago Midway International Airport (MDW) to Indianapolis (IND)plane plane MDW - IND
    2. Take the bus from Indianapolis Airport to Muncie, INbus bus
    6h 15m
    $100–546

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

Calendar55Weekly Planes
Duration1h 25mAverage Duration
Ticket$42Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Winchester.ExpandLaunch map view
  • Distance: 235.9 mi
  • Duration: 5h 51m

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

Barons Bus operates a bus from Chicago to Portland, IN once daily. Tickets cost $21–60 and the journey takes 5h 25m.

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