Rome2Rio

How to get fromChester to Chicagoby bus, plane, bus (Flixbus), train (Amtrak), car, train, or bus (Greyhound)

Find Transport to Chicago

See all options

There are 12 ways to get from Chester to Chicago by bus, plane, bus (Flixbus), train (Amtrak), car, train, or bus (Greyhound)

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

  1. Bus to Newark Liberty International Airport, fly to Chicago O'Hare International Airport

    best
    1. Take the bus from Bedminster to Newarkbus bus
    2. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    5h 7m

  2. Train, train to Philadelphia International Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the train from Gladstone to Newark Broad Sttrain train
    2. Take the train from Newark Penn Station to 30th Street Stationtrain train
    3. Fly from Philadelphia International Airport (PHL) to Chicago O'Hare International Airport (ORD)plane plane PHL - ORD
    7h 52m
    $135–1,111

  3. Bus

    1. Take the bus from Clinton to Allentownbus bus Blu 10Amny / ...
    2. Take the bus from Allentown to Chicago Bus Stationbus bus FlixBus N2640
    19h 59m

  4. Train via Ossining (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Croton-Harmon Amtrak Stationtrain train Empire Service / ...
    2. Take the train from Croton-Harmon Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    23h 35m
    $337–727

  5. Drive 753.3 mi

    1. Drive from Chester to Chicagocar car 753.3 mi
    12h 28m
    $138–199

  6. Bus to Lehigh Valley International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Clinton to Allentown Airportbus bus
    2. Fly from Lehigh Valley International Airport (ABE) to Chicago O'Hare International Airport (ORD)plane plane ABE - ORD
    5h 37m
    $172–450

  7. Train, train to Laguardia Airport, fly to Chicago Midway International Airport

    1. Take the train from Gladstone to Summittrain train
    2. Take the train from Summit to New York Penn Stationtrain train
    3. Take the train from New York Penn Station to Flushing Main Streettrain train
    4. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    7h 29m
    $217–627

  8. Train, train to Laguardia Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Gladstone to Summittrain train
    2. Take the train from Summit to New York Penn Stationtrain train
    3. Take the train from New York Penn Station to Flushing Main Streettrain train
    4. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    7h 50m
    $247–727

  9. Train, train to Philadelphia International Airport, fly to Chicago Midway International Airport

    1. Take the train from Gladstone to Newark Broad Sttrain train
    2. Take the train from Newark Penn Station to 30th Street Stationtrain train
    3. Fly from Philadelphia International Airport (PHL) to Chicago Midway International Airport (MDW)plane plane PHL - MDW
    7h 23m
    $190–1,061

  10. Bus to Newark Liberty International Airport, fly to General Mitchell International Airport, train

    1. Take the bus from Bedminster to Newarkbus bus
    2. Fly from Newark Liberty International Airport (EWR) to General Mitchell International Airport (MKE)plane plane EWR - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain train
    7h 22m

  11. Bus via Baltimore

    1. Take the bus from Newark Penn Station to Baltimorebus bus New York / ...
    2. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus Greyhound US0164
    27h 16m
    $177–388

  12. Train

    1. Take the train from Gladstone to Newark Broad Sttrain train Mneg
    2. Take the train from Newark Penn Station to Chicago Union Stationtrain train Cardinal
    31h
    $386–798

Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD) flights

Calendar146Weekly Planes
Duration2h 58mAverage Duration
Ticket$63Cheapest Price
See schedules

Questions & Answers

Map of how to get from Chester to Chicago.ExpandLaunch map view
  • Distance: 776 mi
  • Duration: 5h 7m

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

You can take a vehicle from Chester to Chicago Bus Station via Clinton and Allentown in around 19h 59m. Alternatively, you can take a vehicle from Chester to Chicago Union Station via Gladstone, Summit, Penn Station, Ny Moynihan Train Hall At Penn Station, and Croton-Harmon Amtrak Station in around 23h 35m.

Airlines
Train operators
Bus 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

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

More Questions & Answers