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

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There are 10 ways to get from Chicago to Chester by plane, train (Amtrak), bus (Greyhound), car, bus, 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 25m
    $146–408

  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 24m
    $78–382

  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
    $274–1,146

  4. Bus via Baltimore

    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 12m
    $135–253

  5. Drive 749.3 mi

    1. Drive from Chicago to Chestercar car 749.3 mi
    12h 28m
    $137–198

  6. Fly Chicago O'Hare International Airport to Philadelphia International Airport, line 37 bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Philadelphia International Airport (PHL)plane plane ORD - PHL
    2. Take the bus from Philadelphia Airport Terminal B to 3rd St & Madison Stbus bus
    4h 45m
    $106–558

  7. Train to General Mitchell International Airport, fly to Philadelphia International Airport

    1. Take the train from Chicago Union Station to Milwaukeetrain train
    2. Fly from General Mitchell International Airport (MKE) to Philadelphia International Airport (PHL)plane plane MKE - PHL
    5h 58m
    $183–821

  8. 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
    $144–910

  9. Bus

    1. Take the bus from Chicago Bus Station to Allentownbus bus FlixBus N2640
    2. Take the bus from Allentown Transportation Center to Philadelphia 30th St Stationbus bus Wilkes-Barre / ...
    21h 56m
    $174–276

  10. Train (Amtrak)

    1. Take the train from Chicago Union Station to Wilmingtontrain train Cardinal
    26h 47m
    $336–669

Chicago to Chester by train and subway (Amtrak)

Calendar7Weekly Services
Duration20h 12mAverage Duration
Ticket$274Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Chester.ExpandLaunch map view
  • Distance: 686.8 mi
  • Duration: 4h 25m

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) 5 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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