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How to get fromChicago to Chesterby plane, train (Amtrak), bus (Greyhound), car, train, or bus (Flixbus)

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There are 9 ways to get from Chicago to Chester by plane, train (Amtrak), bus (Greyhound), car, train, or bus (Flixbus)

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 Philadelphia International Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Philadelphia International Airport (PHL)plane plane MDW - PHL
    4h 26m
    $144–379

  2. Fly Chicago O'Hare International Airport to Lancaster, drive

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Lancaster (LNS)plane plane ORD - LNS
    2. Drive from Lancaster-Airport-LNS to Chestercar car
    5h 23m
    $68–352

  3. Train via Washington (Amtrak)

    1. Take the train from Chicago Union Station to Rockville Amtraktrain train Floridian
    2. Take the train from Washington Union Station to Wilmingtontrain train Carolinian / ...
    20h 12m
    $235–1,179

  4. Bus via Baltimore (Greyhound)

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus Greyhound US0164
    2. Take the bus from Baltimore Downtown Bus Station to Wilmington Bus Stationbus bus Greyhound US0305 / ...
    21h 17m
    $137–212

  5. Drive  749.3 mi

    1. Drive from Chicago to Chestercar car 749.3 mi
    12h 27m
    $137–198

  6. Fly Chicago O'Hare International Airport to Philadelphia International Airport

    1. Fly from Chicago O'Hare International Airport (ORD) to Philadelphia International Airport (PHL)plane plane ORD - PHL
    4h 50m
    $124–229

  7. Fly Chicago Midway International Airport to Baltimore-Washington International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Baltimore-Washington International Airport (BWI)plane plane MDW - BWI
    2. Take the train from BWI Thurgood Marshall to Wilmingtontrain train
    6h 23m
    $144–911

  8. Bus (Flixbus)

    1. Take the bus from Chicago Bus Station to Philadelphia Bus Stationbus bus FlixBus N2642
    22h 22m
    $144–216

  9. Train (Amtrak)

    1. Take the train from Chicago Union Station to Wilmingtontrain train Cardinal
    26h 47m
    $283–712

Chicago to Chester by train and subway (Amtrak)

Calendar7Weekly Services
Duration20h 12mAverage Duration
Ticket$235Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Chester.ExpandLaunch map view
  • Distance: 686.8 mi
  • Duration: 4h 26m

What companies run services between Chicago, IL, USA and Chester, PA, USA?

Southwest Airlines flies from Chicago Midway International Airport (MDW) to Philadelphia International Airport (PHL) 4 times a day. Alternatively, you can take a train from Chicago Union Station to Chester Transit Center via Rockville Amtrak, Rockville, Red Line Center Platform, Union Station, Red Line Center Platform, Washington Union Station, and Wilmington in around 20h 12m.

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