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

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There are 9 ways to get from Naperville 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

    best
    1. Take the train from Naperville to Chicago Union Stationtrain train
    2. Take the train from Chicago Union Station to Du Quoin Stationtrain train
    3. Take the taxi from Du Quoin Station to Chestertaxi taxi
    8h 11m
    $165–326

  2. Drive  319.2 mi

    cheapest
    1. Drive from Naperville to Chestercar car 319.2 mi
    5h 43m
    $59–85

  3. Bus, taxi

    1. Take the bus from Chicago to Marathon Gas Station - Marionbus bus Chicago / ...
    2. Take the taxi from Marathon Gas Station - Marion to Chestertaxi taxi
    9h 47m
    $181–232

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

    1. Take the train from Naperville to Chicago Union Stationtrain train
    2. Fly from Chicago O'Hare International Airport (ORD) to Williamson County Regional Airport (MWA)plane plane ORD - MWA
    3. Take the taxi from Williamson County Regional Airport (MWA) to Chestertaxi taxi
    5h 43m
    $197–361

  5. Train, bus, taxi

    1. Take the train from Naperville to Chicago Union Stationtrain train
    2. Take the bus from Chicago Bus Station to St Louis Bus Stationbus bus
    3. Take the taxi from COLLEGE station to Chestertaxi taxi
    10h 9m
    $163–224

  6. Train to Chicago O'Hare International Airport, fly to Cape Girardeau Municipal Airport, taxi

    1. Take the train from Naperville to Chicago Union Stationtrain train
    2. Fly from Chicago O'Hare International Airport (ORD) to Cape Girardeau Municipal Airport (CGI)plane plane ORD - CGI
    3. Take the taxi from Cape Girardeau Municipal Airport (CGI) to Chestertaxi taxi
    5h 44m
    $227–581

  7. Train to Chicago O'Hare International Airport, fly to Lambert–St. Louis International Airport, train, taxi

    1. Take the train from Naperville to Chicago Union Stationtrain train
    2. Fly from Chicago O'Hare International Airport (ORD) to Lambert–St. Louis International Airport (STL)plane plane ORD - STL
    3. Take the train from LAMBERT AIRPORT TERMINAL #1 station to COLLEGE stationtrain train
    4. Take the taxi from COLLEGE station to Chestertaxi taxi
    6h 55m
    $440–854

  8. Train to Chicago Midway International Airport, fly to Lambert–St. Louis International Airport, train, taxi

    1. Take the train from Naperville to Chicago Union Stationtrain train
    2. Fly from Chicago Midway International Airport (MDW) to Lambert–St. Louis International Airport (STL)plane plane MDW - STL
    3. Take the train from LAMBERT AIRPORT TERMINAL #1 station to COLLEGE stationtrain train
    4. Take the taxi from COLLEGE station to Chestertaxi taxi
    6h 46m
    $190–654

  9. Train to Chicago O'Hare International Airport, fly to Barkley Regional Airport, drive

    1. Take the train from Naperville to Chicago Union Stationtrain train
    2. Fly from Chicago O'Hare International Airport (ORD) to Barkley Regional Airport (PAH)plane plane ORD - PAH
    3. Drive from Barkley Regional Airport (PAH) to Chestercar car
    6h 42m
    $66–320

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

Calendar12Weekly Planes
Duration1h 34mAverage Duration
Ticket$45Cheapest Price
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Comparing Your Travel Options

Map of how to get from Naperville to Chester.ExpandLaunch map view
  • Distance: 355.2 mi
  • Duration: 8h 11m

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

There is no direct connection from Naperville to Chester. However, you can take the train to Chicago Union Station, take the train to Du Quoin Station, then take the taxi to Chester. Alternatively, you can take the line 722 bus to Yorktown Center, take the line 322 bus to 54th Ave CTA Station/Pink Line, take the bus to Cicero & 24th Place, take the line 35 bus to California & 35th Street, take the bus to Marathon Gas Station - Marion, then take the taxi to Chester.

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