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How to get fromChicago to Chesterby train, taxi, bus, car, or plane

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There are 8 ways to get from Chicago to Chester by train, taxi, bus, car, or plane

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

  1. Train, taxi (Amtrak)

    best
    1. Take the train from Chicago Union Station to Du Quoin Stationtrain train Saluki / ...
    2. Take the taxi from Du Quoin Station to Chestertaxi taxi
    6h 7m
    $179–299

  2. Drive 341.1 mi

    cheapest
    1. Drive from Chicago to Chestercar car 341.1 mi
    6h 5m
    $63–90

  3. Bus, taxi

    1. Take the bus from Chicago Bus Station to St Louis Bus Stationbus bus
    2. Take the bus from St. Louis to Carbondalebus bus
    3. Take the taxi from Carbondale to Chestertaxi taxi
    9h 45m
    $151–243

  4. Fly Chicago O'Hare International Airport to Williamson County Regional Airport, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Williamson County Regional Airport (MWA)plane plane ORD - MWA
    2. Take the taxi from Williamson County Regional Airport (MWA) to Chestertaxi taxi
    4h 14m
    $198–365

  5. Fly Chicago O'Hare International Airport to Lambert–St. Louis International Airport, train, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Lambert–St. Louis International Airport (STL)plane plane ORD - STL
    2. Take the train from LAMBERT AIRPORT TERMINAL #1 station to COLLEGE stationtrain train
    3. Take the taxi from COLLEGE station to Chestertaxi taxi
    5h 32m
    $386–848

  6. Fly Chicago Midway International Airport to Lambert–St. Louis International Airport, train, taxi

    1. Fly from Chicago Midway International Airport (MDW) to Lambert–St. Louis International Airport (STL)plane plane MDW - STL
    2. Take the train from LAMBERT AIRPORT TERMINAL #1 station to COLLEGE stationtrain train
    3. Take the taxi from COLLEGE station to Chestertaxi taxi
    5h 16m
    $196–698

  7. Fly Chicago O'Hare International Airport to Cape Girardeau Municipal Airport, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Cape Girardeau Municipal Airport (CGI)plane plane ORD - CGI
    2. Take the taxi from Cape Girardeau Municipal Airport (CGI) to Chestertaxi taxi
    4h 30m
    $218–375

  8. Fly Chicago O'Hare International Airport to Barkley Regional Airport, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to Barkley Regional Airport (PAH)plane plane ORD - PAH
    2. Drive from Barkley Regional Airport (PAH) to Chestercar car
    5h 23m
    $72–334

Chicago O'Hare International Airport (ORD) to Williamson County Regional Airport (MWA) flights

Calendar19Weekly Planes
Duration1h 31mAverage Duration
Ticket$49Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Chester.ExpandLaunch map view
  • Distance: 326.9 mi
  • Duration: 6h 7m

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

There is no direct connection from Chicago to Chester. However, you can take the train to Du Quoin Station then take the taxi to Chester. Alternatively, you can take the bus to St Louis Bus Station, walk to St. Louis, take the bus to Carbondale, then take the taxi to Chester.

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