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How to get fromChester to Chicagoby plane, train (Amtrak), bus (Greyhound), car, train, or bus (Flixbus)

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There are 8 ways to get from Chester to Chicago 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 Philadelphia International Airport to Chicago Midway International Airport

    best
    1. Fly from Philadelphia International Airport (PHL) to Chicago Midway International Airport (MDW)plane plane PHL - MDW
    4h 5m
    $145–408

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

    cheapest
    1. Fly from Philadelphia International Airport (PHL) to Chicago O'Hare International Airport (ORD)plane plane PHL - ORD
    4h 34m
    $90–458

  3. Train via Washington (Amtrak)

    1. Take the train from Wilmington to Washington Union Stationtrain train Northeast Regional / ...
    2. Take the train from Rockville Amtrak to Chicago Union Stationtrain train Floridian
    21h 20m
    $270–1,146

  4. Bus via Baltimore

    1. Take the bus from Wilmington Bus Station to Baltimore Downtown Bus Stationbus bus Greyhound US0305 / ...
    2. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus Greyhound US0164
    22h 18m
    $124–255

  5. Drive 749.3 mi

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

  6. Train to Baltimore-Washington International Airport, fly to Chicago Midway International Airport

    1. Take the train from Wilmington to BWI Thurgood Marshalltrain train
    2. Fly from Baltimore-Washington International Airport (BWI) to Chicago Midway International Airport (MDW)plane plane BWI - MDW
    5h 38m
    $143–908

  7. Bus

    1. Take the bus from Philadelphia 30th St Station to Allentown Transportation Centerbus bus Philadelphia / ...
    2. Take the bus from Allentown to Chicago Bus Stationbus bus FlixBus N2640
    22h 56m
    $166–281

  8. Train (Amtrak)

    1. Take the train from Wilmington to Chicago Union Stationtrain train Cardinal
    28h 3m
    $333–703

Chester to Chicago by train and subway (Amtrak)

Calendar7Weekly Services
Duration21h 20mAverage Duration
Ticket$270Cheapest Price
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Questions & Answers

Map of how to get from Chester to Chicago.ExpandLaunch map view
  • Distance: 684.3 mi
  • Duration: 4h 5m

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

Southwest Airlines and Delta fly from Philadelphia International Airport (PHL) to Chicago Midway International Airport (MDW) every 4 hours. Alternatively, you can take a train from Chester Transit Center to Chicago Union Station via Wilmington, Washington, Columbus Circle, Union Station, Union Station, Red Line Center Platform, Rockville, Red Line Center Platform, and Rockville Amtrak in around 21h 20m.

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