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How to get fromChicago to Milfordby plane, train, bus, train (Amtrak), bus (Flixbus), car, or subway

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There are 9 ways to get from Chicago to Milford by plane, train, bus, train (Amtrak), bus (Flixbus), car, or subway

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 O'Hare International Airport to Boston Logan Airport, train, line 06 bus

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS)plane plane ORD - BOS
    2. Take the train from Back Bay to Framinghamtrain train
    3. Take the bus from Framingham MBTA Station to Spruce Stbus bus
    7h 24m
    $616–1,026

  2. Fly Chicago O'Hare International Airport to Theodore Francis Green State Airport, train

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Theodore Francis Green State Airport (PVD)plane plane ORD - PVD
    2. Take the train from TF Green Airport to Back Baytrain train
    9h 32m
    $76–333

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Framingham Amtraktrain train Lake Shore Limited
    22h 57m
    $325–658

  4. Bus (Flixbus)

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2641 / ...
    2. Take the bus from New York Midtown to Bostonbus bus FlixBus 2610 / ...
    25h 37m
    $186–311

  5. Drive 957.2 mi

    1. Drive from Chicago to Milfordcar car 957.2 mi
    16h 31m
    $175–253

  6. Subway to Chicago Midway International Airport, fly to Boston Logan Airport, train, line 06 bus

    1. Take the subway from Adams/Wabash to Midwaysubway subway
    2. Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane plane MDW - BOS
    3. Take the train from Back Bay to Framinghamtrain train
    4. Take the bus from Framingham MBTA Station to Spruce Stbus bus
    7h 7m
    $116–526

  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
    8h 59m
    $116–582

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

    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 Back Baytrain train
    9h 2m
    $92–403

  9. Fly Chicago Midway International Airport to Bradley International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    2. Take the train from Springfield to Framingham Amtraktrain train
    9h 54m
    $134–575

Chicago to Milford by train and bus (Amtrak)

Calendar5Weekly Services
Duration22h 57mAverage Duration
Ticket$325Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Milford.ExpandLaunch map view
  • Distance: 924.8 mi
  • Duration: 7h 24m

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

Amtrak operates a train from Chicago Union Station to Framingham Amtrak once daily. Tickets cost $320–700 and the journey takes 21h 28m. Alternatively, you can take a bus from Chicago Bus Station to Spruce St via New York Midtown, Boston, Framingham, and Framingham MBTA Station in around 25h 37m.

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