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How to get fromBoston to Chicago Loopby plane, train (Amtrak), bus (Greyhound, Flixbus), car, bus, or train

Find Transport to Chicago Loop

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There are 8 ways to get from Boston to Chicago Loop by plane, train (Amtrak), bus (Greyhound, Flixbus), car, bus, or train

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
    3h 14m
    $83–399

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

    cheapest
    1. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    3h 33m
    $71–340

  3. Train (Amtrak)

    1. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    22h 22m
    $330–700

  4. Bus

    1. Take the bus from Boston to Newark Penn Stationbus bus Greyhound US0235 / ...
    2. Take the bus from Newark Penn Station to Chicago Bus Stationbus bus FlixBus N2641 / ...
    22h 40m
    $160–284

  5. Drive 980.9 mi

    1. Drive from Boston to Chicago Loopcar car 980.9 mi
    16h 49m
    $179–259

  6. 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
    5h 9m
    $100–480

  7. 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
    5h 37m
    $85–410

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

    1. Take the train from South Station 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 52m
    $87–391

Boston to Chicago Loop by train (Amtrak)

Calendar7Weekly Trains
Duration22h 22mAverage Duration
Ticket$330Cheapest Price
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Questions & Answers

Map of how to get from Boston to Chicago Loop.ExpandLaunch map view
  • Distance: 869 mi
  • Duration: 3h 14m

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

Southwest Airlines and Delta fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW) every 4 hours. Alternatively, Amtrak operates a train from Boston to Chicago Union Station once daily. Tickets cost $330–700 and the journey takes 22h 22m.

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