Rome2Rio

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

Find Transport to Chicago

See all options

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 31m
    $204–363

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

    cheapest
    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 20m
    $61–283

  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
    $176–291

  4. Taxi, bus

    1. Take the taxi from Chester to Carbondaletaxi taxi
    2. Take the bus from Carbondale to St. Louisbus bus
    3. Take the bus from St Louis Bus Station to Chicago Bus Stationbus bus
    9h 55m
    $152–237

  5. Drive 337.4 mi

    1. Drive from Chester to Chicagocar car 337.4 mi
    6h 11m
    $62–89

  6. 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 35m
    $225–366

  7. 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 8m
    $171–500

  8. 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
    $386–840

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

Calendar19Weekly Planes
Duration1h 41mAverage Duration
Ticket$44Cheapest Price
See schedules

Questions & Answers

Map of how to get from Chester to Chicago.ExpandLaunch map view
  • Distance: 366.1 mi
  • Duration: 3h 31m

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.

Airlines
Train operators
Bus operators
Other operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides