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

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There are 9 ways to get from Winchester to Chicago by bus, plane, train (Amtrak), taxi, 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. Bus to Washington Dulles International Airport, fly to Chicago O'Hare International Airport

    best
    1. Take the bus from Front Royal Walmart to Dulles International Airportbus bus
    2. Fly from Washington Dulles International Airport (IAD) to Chicago O'Hare International Airport (ORD)plane plane IAD - ORD
    5h 28m
    $242–977

  2. Drive 620.3 mi

    cheapest
    1. Drive from Winchester to Chicagocar car 620.3 mi
    10h 53m
    $114–164

  3. Train (Amtrak)

    1. Take the train from Martinsburg Amtrak Station to Chicago Union Stationtrain train Floridian
    16h 34m
    $275–525

  4. Taxi, bus

    1. Take the taxi from Winchester to Purcellville Park & Ridetaxi taxi
    2. Take the bus from Market St & Harrison St to Frederick Transit Stationbus bus 581
    3. Take the bus from Frederick Bus Station to Chicago Bus Stationbus bus
    19h 16m
    $164–285

  5. Bus to Ronald Reagan Washington National Airport, fly to Chicago Midway International Airport

    1. Take the bus from Crooked Run Park & Ride to Virginia Ave @ 21st St NWbus bus
    2. Fly from Ronald Reagan Washington National Airport (DCA) to Chicago Midway International Airport (MDW)plane plane DCA - MDW
    5h 51m
    $167–670

  6. Bus to Ronald Reagan Washington National Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Crooked Run Park & Ride to Virginia Ave @ 21st St NWbus bus
    2. Fly from Ronald Reagan Washington National Airport (DCA) to Chicago O'Hare International Airport (ORD)plane plane DCA - ORD
    6h 14m
    $177–920

  7. Taxi, train, train to Baltimore-Washington International Airport, fly to Chicago Midway International Airport

    1. Take the taxi from Winchester to DUFFIELDS W VA MARC ebtaxi taxi
    2. Take the train from DUFFIELDS W VA MARC eb to Washington Union Stationtrain train
    3. Take the train from Washington Union Station to BWI Thurgood Marshalltrain train
    4. Fly from Baltimore-Washington International Airport (BWI) to Chicago Midway International Airport (MDW)plane plane BWI - MDW
    7h 1m
    $193–947

  8. Taxi, train, train to Baltimore-Washington International Airport, fly to Chicago O'Hare International Airport

    1. Take the taxi from Winchester to DUFFIELDS W VA MARC ebtaxi taxi
    2. Take the train from DUFFIELDS W VA MARC eb to Washington Union Stationtrain train
    3. Take the train from Washington Union Station to BWI Thurgood Marshalltrain train
    4. Fly from Baltimore-Washington International Airport (BWI) to Chicago O'Hare International Airport (ORD)plane plane BWI - ORD
    7h 28m
    $138–1,007

  9. Bus, bus to Charlottesville, fly to Chicago O'Hare International Airport

    1. Take the bus from Crooked Run Park & Ride to University Commuter Lotbus bus
    2. Take the bus from Gainesville Park and Ride to Alderman Rd / Floyd Dr - Charlottesvillebus bus
    3. Fly from Charlottesville (CHO) to Chicago O'Hare International Airport (ORD)plane plane CHO - ORD
    8h 1m
    $151–446

Washington Dulles International Airport (IAD) to Chicago O'Hare International Airport (ORD) flights

Calendar102Weekly Planes
Duration3h 22mAverage Duration
Ticket$55Cheapest Price
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Questions & Answers

Map of how to get from Winchester to Chicago.ExpandLaunch map view
  • Distance: 680.7 mi
  • Duration: 5h 28m

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

Amtrak operates a train from Martinsburg Amtrak Station to Chicago Union Station once daily. Tickets cost $220–460 and the journey takes 16h 8m.

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