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

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There are 10 ways to get from Chester to Chicago by bus, plane, bus (Greyhound, Flixbus), train (Amtrak), car, or bus (Greyhound)

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Bus to Laguardia Airport, fly to Chicago Midway International Airport

    best
    1. Take the bus from Chester Park Ride to Port Authority Bus Terminalbus bus
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    6h 6m
    $217–583

  2. Bus to Westchester County Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the bus from Chester Park Ride to Main St & Broadwaybus bus
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    7h 23m
    $105–498

  3. Bus

    1. Take the bus from Chester Park Ride to Port Authority Bus Terminalbus bus
    2. Take the bus from Port Authority Bus Terminal to Newark Penn Stationbus bus 108
    3. Take the bus from Newark Penn Station to Chicago Bus Stationbus bus
    19h 42m
    $149–295

  4. Train (Amtrak)

    1. Take the train from Poughkeepsie Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    20h 5m
    $411–759

  5. Drive 782.1 mi

    1. Drive from Chester to Chicagocar car 782.1 mi
    12h 55m
    $143–207

  6. Bus to Laguardia Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Chester Park Ride to Port Authority Bus Terminalbus bus
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    6h 26m
    $227–683

  7. Bus, bus to Newark Liberty International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Chester Park Ride to Port Authority Bus Terminalbus bus
    2. Take the bus from Port Authority Bus Terminal to Terminal Bbus bus
    3. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    6h 48m
    $159–905

  8. Bus to John F. Kennedy International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Chester Park Ride to Port Authority Bus Terminalbus bus
    2. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    6h 47m
    $338–899

  9. Bus, bus to Lehigh Valley International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Chester Park Ride to Port Authority Bus Terminalbus bus
    2. Take the bus from Port Authority Bus Terminal to Lehigh Valley International Airport Trans Bridge Bus Stopbus bus
    3. Fly from Lehigh Valley International Airport (ABE) to Chicago O'Hare International Airport (ORD)plane plane ABE - ORD
    9h 40m
    $134–420

  10. Bus via Baltimore

    1. Take the bus from Chester Park Ride to Port Authority Bus Terminalbus bus
    2. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus bus
    3. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus
    24h 59m
    $167–375

Chester to Chicago by bus

Calendar15Weekly Buses
Duration19h 42mAverage Duration
Ticket$149Cheapest Price
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Questions & Answers

Map of how to get from Chester to Chicago.ExpandLaunch map view
  • Distance: 807.2 mi
  • Duration: 6h 6m

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

You can take a bus from Chester Park Ride to Chicago Bus Station via Port Authority Bus Terminal and Newark Penn Station in around 19h 42m. Alternatively, Amtrak operates a train from Poughkeepsie Amtrak Station to Chicago Union Station once daily. Tickets cost $280–600 and the journey takes 18h 2m.

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