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

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There are 10 ways to get from Ipswich to Chicago by train, plane, bus (Flixbus), train (Amtrak), car, bus, 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. Train to Boston Logan Airport, fly to Chicago Midway International Airport

    best
    1. Take the train from Ipswich to Chelseatrain train
    2. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    5h 26m
    $92–430

  2. Bus (Flixbus)

    1. Take the bus from Boston to New York Midtownbus bus FlixBus 2610 / ...
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    24h 20m
    $180–325

  3. Train

    1. Take the train from Ipswich to North Stationtrain train Newburyport/Rockport Line
    2. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    24h 22m
    $338–714

  4. Drive 1,005.7 mi

    1. Drive from Ipswich to Chicagocar car 1,005.7 mi
    17h 29m
    $184–266

  5. Fly Boston Logan Airport to Chicago O'Hare International Airport

    1. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    5h 51m
    $607–1,020

  6. Train, bus to Manchester Airport, fly to Chicago Midway International Airport

    1. Take the train from Ipswich to North Stationtrain train
    2. Take the bus from Boston to Boston Manchester Airportbus bus
    3. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)plane plane MHT - MDW
    7h 19m
    $112–504

  7. Train, train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport

    1. Take the train from Ipswich to North Stationtrain train
    2. Take the train from Ruggles to TF Green Airporttrain train
    3. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    7h 51m
    $94–424

  8. Train, bus to Manchester Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Ipswich to North Stationtrain train
    2. Take the bus from Boston to Boston Manchester Airportbus bus
    3. Fly from Manchester Airport (MHT) to Chicago O'Hare International Airport (ORD)plane plane MHT - ORD
    7h 54m
    $97–434

  9. Fly Boston Logan Airport to General Mitchell International Airport, train

    1. Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)plane plane BOS - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain train
    7h 55m
    $684–1,989

  10. Bus via Brook Park (Greyhound)

    1. Take the bus from Boston to Cleveland Bus Stationbus bus Greyhound US0171
    2. Take the bus from Cleveland Bus Station to Chicago Bus Stationbus bus Greyhound US0164
    24h 27m
    $155–315

Ipswich to Chicago by train and bus (Flixbus)

Calendar15Weekly Services
Duration24h 20mAverage Duration
Ticket$180Cheapest Price
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Questions & Answers

Map of how to get from Ipswich to Chicago.ExpandLaunch map view
  • Distance: 895.7 mi
  • Duration: 5h 26m

What companies run services between Ipswich, MA, USA and Chicago, IL, USA?

You can take a train from Ipswich to Chicago Bus Station via Chelsea, Chelsea, South Station, Boston, and New York Midtown in around 24h 20m. Alternatively, you can take a train from Ipswich to Chicago Union Station via North Station, North Station, Back Bay, and Boston in around 24h 22m.

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