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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
    $180–306

  2. Drive 319.2 mi

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

  3. Bus, train, taxi

    1. Take the bus from Oakbrook Mall to Illinois Terminalbus bus
    2. Take the train from Champaign-Urbana to Du Quoin Stationtrain train
    3. Take the taxi from Du Quoin Station to Chestertaxi taxi
    9h 21m
    $183–284

  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
    5h 10m
    $203–373

  5. Bus, taxi

    1. Take the bus from Naperville to Chicagobus bus
    2. Take the bus from Chicago Bus Station to Carbondale Intermodal Stationbus bus
    3. Take the taxi from Carbondale Intermodal Station to Chestertaxi taxi
    11h 40m

  6. 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
    6h 27m
    $391–856

  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
    5h 26m
    $223–383

  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
    $200–704

  9. 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
    6h 19m
    $77–342

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 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 Oak Brook Center / Macy's, take the bus to Illinois Terminal, walk to Champaign-Urbana, take the train to Du Quoin Station, then take the taxi to Chester.

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