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

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

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 Bradley International Airport, bus

    best
    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    2. Take the bus from Central Row South Side @ Travelers to Chester Park & Ride @ W Main Stbus bus
    6h 6m
    $104–515

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

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane plane ORD - BDL
    2. Take the bus from Central Row South Side @ Travelers to Chester Park & Ride @ W Main Stbus bus
    6h 36m
    $80–405

  3. Train, bus

    1. Take the train from Chicago Union Station to Springfieldtrain train
    2. Take the train from Springfield to Hartford Amtrak Stationtrain train
    3. Take the bus from Asylum St @ Bushnell Park to Chester Park & Ride @ W Main Stbus bus 921
    22h 36m
    $308–623

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus
    2. Take the bus from Port Authority Bus Terminal to Hartford Union Stationbus bus
    3. Take the bus from Asylum St @ Bushnell Park to Chester Park & Ride @ W Main Stbus bus 921
    22h 46m
    $169–304

  5. Drive 887.5 mi

    1. Drive from Chicago to Chestercar car 887.5 mi
    15h 18m
    $162–234

  6. Fly Chicago Midway International Airport to Laguardia Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Old Saybrook Amtrak Stationtrain train
    8h 51m
    $220–636

  7. Fly Chicago Midway International Airport to Theodore Francis Green State Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Theodore Francis Green State Airport (PVD)plane plane MDW - PVD
    2. Take the train from Providence to Old Saybrook Amtrak Stationtrain train
    8h 34m
    $110–457

  8. Train (Amtrak)

    1. Take the train from Chicago Union Station to Ny Moynihan Train Hall At Penn Stationtrain train Lake Shore Limited / ...
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Old Saybrook Amtrak Stationtrain train Northeast Regional
    24h 40m
    $347–701

  9. Bus, train

    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 New Haven Union Stationbus bus
    4. Take the train from New Haven to Old Saybrook Amtrak Stationtrain train
    27h
    $188–414

Chicago to Chester by train and bus

Calendar7Weekly Services
Duration22h 36mAverage Duration
Ticket$308Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Chester.ExpandLaunch map view
  • Distance: 830.5 mi
  • Duration: 6h 6m

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

You can take a bus from Chicago Bus Station to Chester Park & Ride @ W Main St via New York Midtown, Port Authority Bus Terminal, Hartford Union Station, and Asylum St @ Bushnell Park in around 22h 46m. Alternatively, you can take a train from Chicago Union Station to Chester Center @ Water Street Parking Lot via Ny Moynihan Train Hall At Penn Station, Old Saybrook Amtrak Station, and Stage Rd & Rt 1 in around 24h 40m.

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