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

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There are 10 ways to get from Dorchester to Chicago by plane, bus (Flixbus), train (Amtrak), car, train, or bus

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

  1. Fly Boston Logan Airport to Chicago Midway International Airport

    best
    1. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    4h 56m
    $90–432

  2. Train to Theodore Francis Green State Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the train from Ruggles to TF Green Airporttrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane plane PVD - ORD
    6h 8m
    $81–380

  3. 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 / ...
    23h 20m
    $151–262

  4. Train (Amtrak)

    1. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    23h 36m
    $282–652

  5. Drive 981.1 mi

    1. Drive from Dorchester to Chicagocar car 981.1 mi
    16h 56m
    $180–259

  6. 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 20m
    $605–1,012

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

    1. Take the train from Ruggles to TF Green Airporttrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    5h 41m
    $91–420

  8. Bus to Manchester Airport, fly to Chicago Midway International Airport

    1. Take the bus from Boston to Boston Manchester Airportbus bus
    2. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)plane plane MHT - MDW
    6h 18m
    $111–571

  9. Bus to Manchester Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Boston to Boston Manchester Airportbus bus
    2. Fly from Manchester Airport (MHT) to Chicago O'Hare International Airport (ORD)plane plane MHT - ORD
    6h 52m
    $101–481

  10. 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 26m
    $678–1,976

Dorchester to Chicago by subway and bus (Flixbus)

Calendar15Weekly Services
Duration23h 20mAverage Duration
Ticket$151Cheapest Price
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Questions & Answers

Map of how to get from Dorchester to Chicago.ExpandLaunch map view
  • Distance: 877.8 mi
  • Duration: 4h 56m

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

Southwest Airlines and Delta fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW) every 4 hours. Alternatively, you can take a subway from Fields Corner to Chicago Bus Station via South Station, Boston, and New York Midtown in around 23h 20m.

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