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

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There are 12 ways to get from Chicago to Milford by plane, train, bus (Flixbus, Greyhound), train (Amtrak), 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 11m
    $222–589

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

    cheapest
    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 11m
    $98–464

  3. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2641 / ...
    2. Take the bus from Port Authority Bus Terminal to New Haven Union Stationbus bus New York
    20h 42m
    $149–264

  4. 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
    $303–636

  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 32m
    $152–689

  7. 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 44m
    $344–900

  8. 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
    $118–554

  9. 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 47m
    $112–529

  10. Fly Chicago O'Hare International Airport to Tweed-New Haven Airport, line 206 bus, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Tweed-New Haven Airport (HVN)plane plane ORD - HVN
    2. Take the bus from Lighthouse Park Terminus to Chapel St @ Orange Stbus bus
    3. Take the train from New Haven to Milfordtrain train
    6h 58m
    $180–502

  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 49m
    $309–1,178

  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 52m
    $178–368

Chicago to Milford by bus, foot, and train

Calendar16Weekly Services
Duration20h 42mAverage Duration
Ticket$149Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Milford.ExpandLaunch map view
  • Distance: 800 mi
  • Duration: 6h 11m

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

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 20h 42m. Alternatively, you can take a train from Chicago Union Station to Milford via Springfield and New Haven in around 22h 12m.

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