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How to get fromChicago Loop to Bostonby plane, train (Amtrak), bus (Greyhound), car, bus, train, or bus (Flixbus)

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There are 9 ways to get from Chicago Loop to Boston by plane, train (Amtrak), bus (Greyhound), car, bus, train, or bus (Flixbus)

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 Chicago Midway International Airport to Boston Logan Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane plane MDW - BOS
    3h 51m
    $112–555

  2. Fly Chicago Midway International Airport to Theodore Francis Green State Airport, train

    cheapest
    1. Fly from Chicago Midway International Airport (MDW) to Theodore Francis Green State Airport (PVD)plane plane MDW - PVD
    2. Take the train from TF Green Airport to South Stationtrain train
    6h 32m
    $96–441

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Bostontrain train Lake Shore Limited
    22h 2m
    $310–650

  4. Bus via Brook Park (Greyhound)

    1. Take the bus from Chicago Bus Station to Cleveland Bus Stationbus bus Greyhound US0164
    2. Take the bus from Cleveland Bus Station to Bostonbus bus Greyhound US0171
    22h 5m
    $151–285

  5. Drive 981.1 mi

    1. Drive from Chicago Loop to Bostoncar car 981.1 mi
    16h 52m
    $179–259

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS)plane plane ORD - BOS
    4h 7m
    $102–605

  7. Fly Chicago Midway International Airport to Manchester Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Manchester Airport (MHT)plane plane MDW - MHT
    2. Take the bus from Boston Manchester Airport to Bostonbus bus
    6h 16m
    $140–670

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Manchester Airport (MHT)plane plane ORD - MHT
    2. Take the bus from Boston Manchester Airport to Bostonbus bus
    6h 41m
    $104–490

  9. Bus (Flixbus)

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2642 / ...
    2. Take the bus from New York Midtown to Bostonbus bus FlixBus 2610 / ...
    27h 47m
    $171–284

Chicago Loop to Boston by train (Amtrak)

Calendar7Weekly Trains
Duration22h 2mAverage Duration
Ticket$310Cheapest Price
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Questions & Answers

Map of how to get from Chicago Loop to Boston.ExpandLaunch map view
  • Distance: 869.5 mi
  • Duration: 3h 51m

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

Southwest Airlines and Delta fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS) every 4 hours. Alternatively, Amtrak operates a train from Chicago Union Station to Boston once daily. Tickets cost $310–650 and the journey takes 22h 2m.

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