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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 8m
    $100–476

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

    cheapest
    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 31m
    $70–286

  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
    $137–708

  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 New Haven Union Stationbus bus New York
    23h 48m
    $114–211

  5. Drive 847.9 mi

    1. Drive from Chicago to Milfordcar car 847.9 mi
    14h 20m
    $155–224

  6. Fly Chicago O'Hare International Airport to John F. Kennedy International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK)plane plane ORD - JFK
    2. Take the train from Grand Central Terminal to Milfordtrain train
    6h 45m
    $782–1,048

  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 33m
    $126–830

  8. 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 4m
    $92–650

  9. 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 32m
    $70–517

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

    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 44m
    $102–499

  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 51m
    $136–872

  12. Bus, train

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore Downtown Bus Station to Port Authority Bus Terminalbus bus
    3. Take the train from Grand Central Terminal to Milfordtrain train
    23h 53m
    $126–277

Chicago to Milford by train (Amtrak)

Calendar7Weekly Trains
Duration22h 12mAverage Duration
Ticket$137Cheapest Price
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Questions & Answers

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 Milford via New York Midtown, Port Authority Bus Terminal, New Haven Union Station, and New Haven in around 23h 48m.

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