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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
    5h 7m
    $209–602

  2. Drive, train via Washington

    cheapest
    1. Drive from Chestertown to EDGEWOOD MARC sbcar car
    2. Take the train from EDGEWOOD MARC sb to Washington Union Stationtrain train
    3. Take the train from Rockville Amtrak to Chicago Union Stationtrain train
    21h 57m
    $106–344

  3. Taxi, bus

    1. Take the taxi from Chestertown to Kent Narrows P & Rtaxi taxi
    2. Take the bus from Kent Narrows P & R to N CAPITOL ST & H ST nbbus bus 250 / ...
    3. Take the bus from Washington Union Station to Chicago Bus Stationbus bus
    20h 58m
    $155–290

  4. Drive 748.8 mi

    1. Drive from Chestertown to Chicagocar car 748.8 mi
    13h 2m
    $137–198

  5. 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 23m
    $219–532

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

    1. Drive from Chestertown to EDGEWOOD MARC sbcar car
    2. Take the train from EDGEWOOD MARC sb to NEW CARROLLTON MARC sbtrain train
    3. Fly from Ronald Reagan Washington National Airport (DCA) to Chicago Midway International Airport (MDW)plane plane DCA - MDW
    7h 24m
    $150–843

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

    1. Drive from Chestertown to EDGEWOOD MARC sbcar car
    2. Take the train from EDGEWOOD MARC sb to NEW CARROLLTON MARC sbtrain train
    3. Fly from Ronald Reagan Washington National Airport (DCA) to Chicago O'Hare International Airport (ORD)plane plane DCA - ORD
    7h 40m
    $120–643

  8. 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 41m
    $221–834

  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
    7h 4m
    $246–794

  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 28m
    $271–807

  11. Drive, bus

    1. Drive from Chestertown to Bayner Rd & Sandalwood Rdcar car
    2. Take the bus from 701 E. Joppa Rd. Black and Decker to York Transfer Centerbus bus 83S
    3. Take the bus from York Transfer Center to Market St. at 5th St.bus bus 83N
    4. Take the bus from Harrisburg Bus Station to Chicago Bus Stationbus bus
    25h 32m
    $106–227

  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 29m
    $134–618

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

Calendar45Weekly Planes
Duration2h 47mAverage Duration
Ticket$74Cheapest Price
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Questions & Answers

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 the taxi to Kent Narrows P & R, take the bus to N CAPITOL ST & H ST nb, walk to Washington Union Station, then take the bus to Chicago Bus Station.

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