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

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There are 12 ways to get from Chestertown to Chicago by taxi, bus, plane, 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. Taxi, bus to Baltimore-Washington International Airport, fly to Chicago Midway International Airport

    best
    1. Take the taxi from Chestertown to Kent Island, MDtaxi taxi
    2. Take the bus from Kent Island, MD to BWI-Thurgood Marshall Airportbus bus
    3. Fly from Baltimore-Washington International Airport (BWI) to Chicago Midway International Airport (MDW)plane plane BWI - MDW
    4h 52m
    $249–480

  2. Drive, train to Ronald Reagan Washington National Airport, fly to Chicago Midway International Airport

    cheapest
    1. Drive from Chestertown to Edgewoodcar car
    2. Take the train from Edgewood to Washington Union Stationtrain train
    3. Fly from Ronald Reagan Washington National Airport (DCA) to Chicago Midway International Airport (MDW)plane plane DCA - MDW
    7h 5m
    $120–643

  3. Drive, bus (Greyhound)

    1. Drive from Chestertown to Baltimorecar car
    2. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus Greyhound US0164
    21h 52m
    $126–248

  4. Drive, train via Washington

    1. Drive from Chestertown to Edgewoodcar car
    2. Take the train from Edgewood to Washington Union Stationtrain train
    3. Take the train from Rockville Amtrak to Chicago Union Stationtrain train
    22h 6m
    $246–524

  5. Drive 748.8 mi

    1. Drive from Chestertown to Chicagocar car 748.8 mi
    13h 11m
    $137–198

  6. Taxi, bus to Baltimore-Washington International Airport, fly to Chicago O'Hare International Airport

    1. Take the taxi from Chestertown to Kent Island, MDtaxi taxi
    2. Take the bus from Kent Island, MD to BWI-Thurgood Marshall Airportbus bus
    3. Fly from Baltimore-Washington International Airport (BWI) to Chicago O'Hare International Airport (ORD)plane plane BWI - ORD
    5h 20m
    $309–730

  7. Taxi, train to Philadelphia International Airport, fly to Chicago Midway International Airport

    1. Take the taxi from Chestertown to Aberdeen Amtrak Stationtaxi taxi
    2. Take the train from Aberdeen Amtrak Station to 30th Street Stationtrain train
    3. Fly from Philadelphia International Airport (PHL) to Chicago Midway International Airport (MDW)plane plane PHL - MDW
    6h 28m
    $300–572

  8. Drive, train to Ronald Reagan Washington National Airport, fly to Chicago O'Hare International Airport

    1. Drive from Chestertown to Edgewoodcar car
    2. Take the train from Edgewood to Washington Union Stationtrain train
    3. Fly from Ronald Reagan Washington National Airport (DCA) to Chicago O'Hare International Airport (ORD)plane plane DCA - ORD
    7h 28m
    $180–893

  9. Taxi, train to Philadelphia International Airport, fly to Chicago O'Hare International Airport

    1. Take the taxi from Chestertown to Aberdeen Amtrak Stationtaxi taxi
    2. Take the train from Aberdeen Amtrak Station to 30th Street Stationtrain train
    3. Fly from Philadelphia International Airport (PHL) to Chicago O'Hare International Airport (ORD)plane plane PHL - ORD
    6h 57m
    $270–422

  10. Taxi, bus to Baltimore-Washington International Airport, fly to General Mitchell International Airport, train

    1. Take the taxi from Chestertown to Kent Island, MDtaxi taxi
    2. Take the bus from Kent Island, MD to BWI-Thurgood Marshall Airportbus bus
    3. Fly from Baltimore-Washington International Airport (BWI) to General Mitchell International Airport (MKE)plane plane BWI - MKE
    4. Take the train from Milwaukee to Chicago Union Stationtrain train
    7h 21m
    $265–894

  11. Drive, bus via Harrisburg

    1. Drive from Chestertown to Bayner Rd & Sandalwood Rdcar car
    2. Take the bus from Baltimore Downtown Bus Station to Harrisburg Bus Stationbus bus
    3. Take the bus from Harrisburg Bus Station to Chicago Bus Stationbus bus
    23h 24m
    $138–245

  12. Drive, train (Amtrak)

    1. Drive from Chestertown to Edgewoodcar car
    2. Take the train from Baltimore Penn Station to Chicago Union Stationtrain train Cardinal
    28h 55m
    $304–676

Baltimore-Washington International Airport (BWI) to Chicago Midway International Airport (MDW) flights

Calendar56Weekly Planes
Duration2h 18mAverage Duration
Ticket$77Cheapest Price
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Questions & Answers

Map of how to get from Chestertown to Chicago.ExpandLaunch map view
  • Distance: 680.1 mi
  • Duration: 4h 52m

What companies run services between Chestertown, MD, USA and Chicago, IL, USA?

There is no direct connection from Chestertown to Chicago. However, you can take the taxi to Kent Island, MD, take the bus to BWI-Thurgood Marshall Airport, walk to Baltimore-Washington International Airport (BWI) airport, fly to Chicago Midway International Airport (MDW), walk to Midway, then take the subway to Harold Washington Library. Alternatively, you can take a vehicle from Chestertown to Chicago Bus Station via Baltimore and Baltimore Downtown Bus Station in around 21h 52m.

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