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How to get fromLeesburg to Chicagoby plane, bus (Greyhound), subway, train, or car

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There are 9 ways to get from Leesburg to Chicago by plane, bus (Greyhound), subway, train, or car

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

  1. Fly Washington Dulles International Airport to Chicago O'Hare International Airport

    best
    1. Fly from Washington Dulles International Airport (IAD) to Chicago O'Hare International Airport (ORD)plane plane IAD - ORD
    4h 31m
    $185–919

  2. Subway to Baltimore-Washington International Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the subway from Ashburn, Silver Line Center Platform to New Carrollton, Orange Line Center Platformsubway subway
    2. Fly from Baltimore-Washington International Airport (BWI) to Chicago O'Hare International Airport (ORD)plane plane BWI - ORD
    6h 46m
    $72–387

  3. Bus

    1. Take the bus from Market St & Harrison St to Frederick Transit Stationbus bus 581
    2. Take the bus from Frederick Bus Station to Chicago Bus Stationbus bus Greyhound US0164
    17h 12m
    $101–211

  4. Subway, train

    1. Take the subway from Ashburn, Silver Line Center Platform to Farragut West, Blue/Orange/Silver Line Track 1 Platformsubway subway S
    2. Take the train from Rockville Amtrak to Chicago Union Stationtrain train Floridian
    20h 14m
    $245–517

  5. Drive 656.3 mi

    1. Drive from Leesburg to Chicagocar car 656.3 mi
    11h 38m
    $120–173

  6. Subway to Ronald Reagan Washington National Airport, fly to Chicago Midway International Airport

    1. Take the subway from Ashburn, Silver Line Center Platform to Rosslyn, Blue/Orange/Silver Line Track 1 Platformsubway subway
    2. Fly from Ronald Reagan Washington National Airport (DCA) to Chicago Midway International Airport (MDW)plane plane DCA - MDW
    5h 7m
    $117–622

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

    1. Take the subway from Ashburn, Silver Line Center Platform to Rosslyn, Blue/Orange/Silver Line Track 1 Platformsubway subway
    2. Fly from Ronald Reagan Washington National Airport (DCA) to Chicago O'Hare International Airport (ORD)plane plane DCA - ORD
    5h 30m
    $127–872

  8. Subway to Baltimore-Washington International Airport, fly to Chicago Midway International Airport

    1. Take the subway from Ashburn, Silver Line Center Platform to New Carrollton, Orange Line Center Platformsubway subway
    2. Fly from Baltimore-Washington International Airport (BWI) to Chicago Midway International Airport (MDW)plane plane BWI - MDW
    6h 18m
    $127–327

  9. Fly Washington Dulles International Airport to South Bend, train

    1. Fly from Washington Dulles International Airport (IAD) to South Bend (SBN)plane plane IAD - SBN
    2. Take the train from South Bend Airport to Van Buren St.train train
    6h 17m
    $126–1,229

Leesburg to Chicago by bus

Calendar7Weekly Buses
Duration17h 12mAverage Duration
Ticket$101Cheapest Price
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Questions & Answers

Map of how to get from Leesburg to Chicago.ExpandLaunch map view
  • Distance: 621.1 mi
  • Duration: 4h 31m

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

United Airlines flies from Washington Dulles International Airport (IAD) to Chicago O'Hare International Airport (ORD) hourly. Alternatively, you can take a bus from Market St & Harrison St to Chicago Bus Station via Frederick Bus Station in around 17h 12m.

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