Rome2Rio

How to get fromChicago to Chestertownby plane, bus, taxi, train, car or subway

Find Transport to Chestertown

See all options

There are 12 ways to get from Chicago to Chestertown by plane, bus, taxi, train, car, or subway

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 Chicago Midway International Airport to Baltimore-Washington International Airport, bus, taxi

    best
    1. Fly from Chicago Midway International Airport (MDW) to Baltimore-Washington International Airport (BWI)plane plane MDW - BWI
    2. Take the bus from BWI-Thurgood Marshall Airport to Kent Island, MDbus bus
    3. Take the taxi from Kent Island, MD to Chestertowntaxi taxi
    5h 41m
    $218–625

  2. Bus, drive

    cheapest
    1. Take the bus from Chicago Bus Station to Harrisburg Bus Stationbus bus
    2. Take the bus from Market St. at 5th St. to York Transfer Centerbus bus 83N
    3. Take the bus from York Transfer Center to 701 E. Joppa Rd. Black and Deckerbus bus 83S
    4. Drive from Bayner Rd & Sandalwood Rd to Chestertowncar car
    24h 7m
    $109–193

  3. Bus, taxi

    1. Take the bus from Chicago Bus Station to Washington Union Stationbus bus
    2. Take the bus from N CAPITOL ST & H ST NW sb to Kent Narrows P & Rbus bus 250 / ...
    3. Take the taxi from Kent Narrows P & R to Chestertowntaxi taxi
    20h 19m
    $155–297

  4. Train, drive via Washington

    1. Take the train from Chicago Union Station to Rockville Amtraktrain train
    2. Take the train from Washington Union Station to Edgewoodtrain train
    3. Drive from Edgewood to Chestertowncar car
    21h 31m
    $126–348

  5. Drive 752.1 mi

    1. Drive from Chicago to Chestertowncar car 752.1 mi
    13h
    $138–199

  6. Fly Chicago O'Hare International Airport to Baltimore-Washington International Airport, bus, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Baltimore-Washington International Airport (BWI)plane plane ORD - BWI
    2. Take the bus from BWI-Thurgood Marshall Airport to Kent Island, MDbus bus
    3. Take the taxi from Kent Island, MD to Chestertowntaxi taxi
    6h 9m
    $222–535

  7. Fly Chicago Midway International Airport to Ronald Reagan Washington National Airport, train, drive

    1. Fly from Chicago Midway International Airport (MDW) to Ronald Reagan Washington National Airport (DCA)plane plane MDW - DCA
    2. Take the train from Washington Union Station to Edgewoodtrain train
    3. Drive from Edgewood to Chestertowncar car
    7h 59m
    $170–940

  8. Fly Chicago O'Hare International Airport to Ronald Reagan Washington National Airport, train, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to Ronald Reagan Washington National Airport (DCA)plane plane ORD - DCA
    2. Take the train from Washington Union Station to Edgewoodtrain train
    3. Drive from Edgewood to Chestertowncar car
    8h 19m
    $140–790

  9. Fly Chicago Midway International Airport to Philadelphia International Airport, train, taxi

    1. Fly from Chicago Midway International Airport (MDW) to Philadelphia International Airport (PHL)plane plane MDW - PHL
    2. Take the train from 30th Street Station to Aberdeen Amtrak Stationtrain train
    3. Take the taxi from Aberdeen Amtrak Station to Chestertowntaxi taxi
    7h 13m
    $216–855

  10. Fly Chicago O'Hare International Airport to Philadelphia International Airport, train, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Philadelphia International Airport (PHL)plane plane ORD - PHL
    2. Take the train from 30th Street Station to Aberdeen Amtrak Stationtrain train
    3. Take the taxi from Aberdeen Amtrak Station to Chestertowntaxi taxi
    7h 38m
    $240–795

  11. Fly Chicago O'Hare International Airport to Washington Dulles International Airport, subway, train, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to Washington Dulles International Airport (IAD)plane plane ORD - IAD
    2. Take the subway from Washington Dulles International Airport, Silver Line Center Platform to Farragut West, Blue/Orange/Silver Line Track 1 Platformsubway subway
    3. Take the train from Washington Union Station to Edgewoodtrain train
    4. Drive from Edgewood to Chestertowncar car
    9h 5m
    $170–845

  12. Train, drive (Amtrak)

    1. Take the train from Chicago Union Station to Baltimore Penn Stationtrain train Cardinal
    2. Drive from Edgewood to Chestertowncar car
    27h 50m
    $142–436

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

Calendar36Weekly Planes
Duration2h 5mAverage Duration
Ticket$78Cheapest Price
See schedules

Questions & Answers

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

There is no direct connection from Chicago to Chestertown. However, you can take the subway to Midway, walk to Chicago-Midway-Airport-MDW airport, fly to Baltimore-Washington International Airport (BWI), walk to BWI-Thurgood Marshall Airport, take the bus to Kent Island, MD, then take the taxi to Chestertown. Alternatively, you can take the bus to Washington Union Station, walk to N CAPITOL ST & H ST NW sb, take the bus to Kent Narrows P & R, then take the taxi to Chestertown.

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

Trips from Chicago

Trips to Chestertown

Popular routes