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

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There are 12 ways to get from Chicago to Milford by plane, train, train (Amtrak), bus (Flixbus, Greyhound), car, 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 Chicago Midway International Airport to Laguardia Airport, train

    best
    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from 125th Street - Harlem to Milfordtrain train
    6h 23m
    $222–689

  2. Fly Chicago O'Hare International Airport to Westchester County Airport, train

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the train from Stamford to Milfordtrain train
    7h 58m
    $92–437

  3. Train via Springfield (Amtrak)

    1. Take the train from Chicago Union Station to Springfieldtrain train Lake Shore Limited
    2. Take the train from Springfield to New Haventrain train Amtrak Hartford Line / ...
    22h 12m
    $544–845

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2640 / ...
    2. Take the bus from Port Authority Bus Terminal to Bridgeport Bus Stopbus bus Greyhound US0255s
    24h 19m
    $167–246

  5. Drive  847.9 mi

    1. Drive from Chicago to Milfordcar car 847.9 mi
    14h 22m
    $155–224

  6. Fly Chicago O'Hare International Airport to Laguardia Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    2. Take the train from 125th Street - Harlem to Milfordtrain train
    6h 40m
    $152–529

  7. 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 Windsor Locks to New Haventrain train
    6h 41m
    $166–763

  8. Fly Chicago O'Hare International Airport to Newark Liberty International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane plane ORD - EWR
    2. Take the train from Newark Liberty International Airport to Bridgeport Amtrak Stationtrain train
    7h 30m
    $164–931

  9. Fly Chicago O'Hare International Airport to Bradley International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane plane ORD - BDL
    2. Take the train from Windsor Locks to New Haventrain train
    7h 10m
    $126–543

  10. Fly Chicago O'Hare International Airport to Tweed-New Haven Airport

    1. Fly from Chicago O'Hare International Airport (ORD) to Tweed-New Haven Airport (HVN)plane plane ORD - HVN
    7h 5m
    $162–570

  11. Train

    1. Take the train from Chicago Union Station to Ny Moynihan Train Hall At Penn Stationtrain train
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Stamford Amtrak Stationtrain train
    3. Take the train from Stamford to Milfordtrain train
    22h 54m
    $548–1,380

  12. Bus, train

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore to New Yorkbus bus
    3. Take the train from Grand Central Terminal to Milfordtrain train
    24h 42m
    $199–317

Chicago to Milford by train (Amtrak)

Calendar7Weekly Trains
Duration22h 12mAverage Duration
Ticket$544Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Milford.ExpandLaunch map view
  • Distance: 800 mi
  • Duration: 6h 23m

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

You can take a train from Chicago Union Station to Milford via Springfield and New Haven in around 22h 12m. Alternatively, you can take a bus from Chicago Bus Station to River St. at Milford Railroad Station via New York Midtown, Port Authority Bus Terminal, and Bridgeport Transportation Center in around 24h 19m.

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