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How to get fromMilford to Chicagoby train, plane, train (Amtrak), bus (Greyhound, Flixbus), car, or bus

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There are 11 ways to get from Milford to Chicago by train, plane, train (Amtrak), bus (Greyhound, Flixbus), 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. Train to Laguardia Airport, fly to Chicago Midway International Airport

    best
    1. Take the train from Milford to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    6h 17m
    $222–688

  2. Train to Bradley International Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the train from New Haven to Windsor Lockstrain train
    2. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    7h 22m
    $101–422

  3. Train

    1. Take the train from Milford to 125th Street - Harlemtrain train
    2. Take the train from 125th Street - Harlem to Croton-Harmontrain train
    3. Take the train from Croton-Harmon Amtrak Station to Chicago Union Stationtrain train
    22h 41m
    $527–842

  4. Bus

    1. Take the bus from Bridgeport Bus Stop to Port Authority Bus Terminalbus bus Greyhound US0255s
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    25h 37m
    $162–258

  5. Drive  847.9 mi

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

  6. Train to Laguardia Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Milford to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    6h 38m
    $152–528

  7. Train to Bradley International Airport, fly to Chicago Midway International Airport

    1. Take the train from New Haven to Windsor Lockstrain train
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    6h 49m
    $121–522

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

    1. Fly from Tweed-New Haven Airport (HVN) to Chicago O'Hare International Airport (ORD)plane plane HVN - ORD
    6h 22m
    $122–426

  9. Train to Westchester County Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Milford to Stamfordtrain train
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    7h 58m
    $128–627

  10. Train to Laguardia Airport, fly to General Mitchell International Airport, train

    1. Take the train from Milford to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to General Mitchell International Airport (MKE)plane plane LGA - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain train
    8h 51m
    $217–922

  11. Train, bus

    1. Take the train from Milford to Grand Central Terminaltrain train
    2. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus bus
    3. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus
    26h 28m
    $190–299

Milford to Chicago by train

Calendar7Weekly Trains
Duration22h 41mAverage Duration
Ticket$527Cheapest Price
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Comparing Your Travel Options

Map of how to get from Milford to Chicago.ExpandLaunch map view
  • Distance: 800.2 mi
  • Duration: 6h 17m

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

You can take a train from Milford to Chicago Union Station via 125th Street - Harlem and Croton-Harmon Amtrak Station in around 22h 41m. Alternatively, you can take a bus from River St. at Milford Railroad Station to Chicago Bus Station via Bridgeport Bus Stop, Port Authority Bus Terminal, and New York Midtown in around 25h 37m.

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