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How to get fromChester to Chicagoby taxi, plane, train, bus, or car

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

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

  1. Taxi to Williamson County Regional Airport, fly to Chicago O'Hare International Airport

    best
    1. Take the taxi from Chester to Williamson County Regional Airport (MWA)taxi taxi
    2. Fly from Williamson County Regional Airport (MWA) to Chicago O'Hare International Airport (ORD)plane plane MWA - ORD
    3h 36m
    $199–353

  2. Drive  337.7 mi

    cheapest
    1. Drive from Chester to Chicagocar car 337.7 mi
    6h 10m
    $58–84

  3. Taxi, train (Amtrak)

    1. Take the taxi from Chester to Du Quoin Stationtaxi taxi
    2. Take the train from Du Quoin Station to Chicago Union Stationtrain train Saluki / ...
    6h 14m
    $236–351

  4. Taxi, bus

    1. Take the taxi from Chester to Carbondale Intermodal Stationtaxi taxi
    2. Take the bus from Carbondale Intermodal Station to St Louis Bus Stationbus bus
    3. Take the bus from St Louis Bus Station to Chicago Bus Stationbus bus
    9h 50m
    $152–200

  5. Taxi to Cape Girardeau Municipal Airport, fly to Chicago O'Hare International Airport

    1. Take the taxi from Chester to Cape Girardeau Municipal Airport (CGI)taxi taxi
    2. Fly from Cape Girardeau Municipal Airport (CGI) to Chicago O'Hare International Airport (ORD)plane plane CGI - ORD
    3h 47m
    $230–506

  6. Taxi, train to Lambert–St. Louis International Airport, fly to Chicago Midway International Airport

    1. Take the taxi from Chester to COLLEGE stationtaxi taxi
    2. Take the train from COLLEGE station to LAMBERT AIRPORT TERMINAL #1 stationtrain train
    3. Fly from Lambert–St. Louis International Airport (STL) to Chicago Midway International Airport (MDW)plane plane STL - MDW
    5h 6m
    $171–540

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

    1. Take the taxi from Chester to COLLEGE stationtaxi taxi
    2. Take the train from COLLEGE station to LAMBERT AIRPORT TERMINAL #1 stationtrain train
    3. Fly from Lambert–St. Louis International Airport (STL) to Chicago O'Hare International Airport (ORD)plane plane STL - ORD
    5h 31m
    $436–840

  8. Drive to Barkley Regional Airport, fly to Chicago O'Hare International Airport

    1. Drive from Chester to Barkley Regional Airport (PAH)car car
    2. Fly from Barkley Regional Airport (PAH) to Chicago O'Hare International Airport (ORD)plane plane PAH - ORD
    4h 23m
    $60–291

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

Calendar12Weekly Planes
Duration1h 46mAverage Duration
Ticket$38Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chester to Chicago.ExpandLaunch map view
  • Distance: 366.1 mi
  • Duration: 3h 36m

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

There is no direct connection from Chester to Chicago. However, you can take the taxi to Williamson County Regional Airport (MWA) airport, fly to Chicago O'Hare International Airport (ORD), walk to O'Hare, then take the subway to Jackson-Blue. Alternatively, you can take the taxi to Du Quoin Station then take the train to Chicago Union Station.

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