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How to get fromWinchester to Milwaukeeby bus, plane, train (Amtrak), bus (Greyhound, Flixbus), car, taxi, or train

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There are 7 ways to get from Winchester to Milwaukee by bus, plane, train (Amtrak), bus (Greyhound, Flixbus), car, taxi, 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 Ronald Reagan Washington National Airport, fly to General Mitchell International Airport

    best
    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 General Mitchell International Airport (MKE)plane plane DCA - MKE
    5h 51m
    $488–1,168

  2. Drive 708.1 mi

    cheapest
    1. Drive from Winchester to Milwaukeecar car 708.1 mi
    12h 36m
    $130–187

  3. Train (Amtrak)

    1. Take the train from Martinsburg Amtrak Station to Chicago Union Stationtrain train Floridian
    2. Take the train from Chicago Union Station to Milwaukeetrain train Hiawatha Service / ...
    19h 3m
    $302–585

  4. Bus

    1. Take the bus from Crooked Run Park & Ride to 14th St @ F St NWbus bus
    2. Take the bus from Washington Union Station to Chicago Bus Stationbus bus
    3. Take the bus from Chicago Bus Station to Milwaukee Intermodal Stationbus bus
    23h
    $169–300

  5. Taxi, train, train to Baltimore-Washington International Airport, fly to General Mitchell 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 General Mitchell International Airport (MKE)plane plane BWI - MKE
    7h 1m
    $184–1,295

  6. Bus to Washington Dulles International Airport, fly to Chicago O'Hare International Airport, bus

    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
    3. Take the bus from Chicago to Milwaukee Intermodal Stationbus bus
    7h 13m
    $253–1,000

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

    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
    3. Take the bus from Chicago to Milwaukee Intermodal Stationbus bus
    7h 59m
    $188–943

Ronald Reagan Washington National Airport (DCA) to General Mitchell International Airport (MKE) flights

Calendar74Weekly Planes
Duration3h 9mAverage Duration
Ticket$169Cheapest Price
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Questions & Answers

Map of how to get from Winchester to Milwaukee.ExpandLaunch map view
  • Distance: 733.9 mi
  • Duration: 5h 51m

What companies run services between Winchester, VA, USA and Milwaukee, WI, USA?

You can take a vehicle from Winchester to Milwaukee via Martinsburg Amtrak Station and Chicago Union Station in around 19h 3m. Alternatively, you can take a vehicle from Winchester to Milwaukee Intermodal Station via Crooked Run Park & Ride, 14th St @ F St NW, 13 St NW+F St NW, Massachusetts Av NE+1 St NE, Washington Union Station, and Chicago Bus Station in around 23h.

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