Rome2Rio

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

Find Transport to Chicago

See all options

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 Islandtaxi taxi
    2. Take the bus from Kent Island to Baltimorebus bus
    3. Fly from Baltimore-Washington International Airport (BWI) to Chicago Midway International Airport (MDW)plane plane BWI - MDW
    4h 52m
    $249–500

  2. Drive  748.8 mi

    cheapest
    1. Drive from Chestertown to Chicagocar car 748.8 mi
    13h 10m
    $137–198

  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 43m
    $194–277

  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 5m
    $426–684

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

    1. Take the taxi from Chestertown to Kent Islandtaxi taxi
    2. Take the bus from Kent Island to Baltimorebus bus
    3. Fly from Baltimore-Washington International Airport (BWI) to Chicago O'Hare International Airport (ORD)plane plane BWI - ORD
    5h 22m
    $189–550

  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 5m
    $147–679

  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 34m
    $315–583

  8. 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 32m
    $177–679

  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 58m
    $285–433

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

    1. Take the taxi from Chestertown to Kent Islandtaxi taxi
    2. Take the bus from Kent Island to Baltimorebus 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
    $294–984

  11. Taxi, bus, train

    1. Take the taxi from Chestertown to Odessa Park & Ridetaxi taxi
    2. Take the bus from Odessa Park & Ride to Wilmington Tcbus bus 301
    3. Take the train from Wilmington to Jefferson Stationtrain train Wil
    4. Take the bus from Philadelphia Bus Station to Chicago Bus Stationbus bus
    24h 23m
    $283–392

  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
    $514–876

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

Calendar46Weekly Planes
Duration2h 18mAverage Duration
Ticket$81Cheapest Price
See schedules

Comparing Your Travel Options

Map of how to get from Chestertown to Chicago.ExpandLaunch map view
  • Distance: 680.3 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, take the bus to Baltimore, 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.

Airlines
Train operators
Bus operators
Other operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound