Rome2Rio

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

Find Transport to Chester

See all options

There are 10 ways to get from Chicago to Chester by plane, bus, bus (Flixbus), train (Amtrak), car, train, 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. Fly Chicago Midway International Airport to Laguardia Airport, bus

    best
    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the bus from Port Authority Bus Terminal to Chester Park Ridebus bus
    6h 27m
    $220–593

  2. Fly Chicago O'Hare International Airport to Westchester County Airport, bus

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the bus from White Plains Bus Center to Chester Park Ridebus bus
    7h 59m
    $110–528

  3. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2641 / ...
    2. Take the bus from Port Authority Bus Terminal to Chester Park Ridebus bus ShortLine Hudson
    19h 32m
    $165–287

  4. Train (Amtrak)

    1. Take the train from Chicago Union Station to Poughkeepsie Amtrak Stationtrain train Lake Shore Limited
    20h 1m
    $416–747

  5. Drive 782.2 mi

    1. Drive from Chicago to Chestercar car 782.2 mi
    12h 56m
    $143–207

  6. Fly Chicago O'Hare International Airport to Laguardia Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    2. Take the bus from Port Authority Bus Terminal to Chester Park Ridebus bus
    6h 47m
    $230–693

  7. Fly Chicago O'Hare International Airport to John F. Kennedy International Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK)plane plane ORD - JFK
    2. Take the bus from Port Authority Bus Terminal to Chester Park Ridebus bus
    6h 58m
    $342–909

  8. Fly Chicago O'Hare International Airport to Newark Liberty International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane plane ORD - EWR
    2. Take the train from Secaucus Lower Level to Harrimantrain train
    7h 45m
    $148–908

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

    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 Ny Moynihan Train Hall At Penn Stationtrain train
    3. Take the bus from Port Authority Bus Terminal to Chester Park Ridebus bus
    8h 17m
    $184–1,021

  10. Bus via Baltimore

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore Downtown Bus Station to Port Authority Bus Terminalbus bus
    3. Take the bus from Port Authority Bus Terminal to Chester Park Ridebus bus
    23h 45m
    $176–385

Chicago to Chester by bus

Calendar16Weekly Buses
Duration19h 32mAverage Duration
Ticket$165Cheapest Price
See schedules

Questions & Answers

Map of how to get from Chicago to Chester.ExpandLaunch map view
  • Distance: 830.4 mi
  • Duration: 6h 27m

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

You can take a bus from Chicago Bus Station to Chester Park Ride via New York Midtown, 8 Av/W 31 St, 8 Av/W 41 St, and Port Authority Bus Terminal in around 19h 32m. Alternatively, Amtrak operates a train from Chicago Union Station to Poughkeepsie Amtrak Station once daily. Tickets cost $280–600 and the journey takes 18h 43m.

Airlines
Train operators
Bus 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

More Questions & Answers