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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 30m
    $115–585

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

    cheapest
    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 48m
    $65–315

  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 40m
    $226–510

  4. Bus

    1. Take the bus from New Haven Union Station to Port Authority Bus Terminalbus bus Providence
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640
    25h 8m
    $124–226

  5. Drive 847.9 mi

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

  6. Train to John F. Kennedy International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Milford to Grand Central Terminaltrain train
    2. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    7h 5m
    $76–307

  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
    7h 2m
    $116–829

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

    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 25m
    $76–559

  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
    8h 1m
    $72–329

  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 58m
    $289–739

  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
    25h 36m
    $168–326

Milford to Chicago by train

Calendar7Weekly Trains
Duration22h 40mAverage Duration
Ticket$226Cheapest Price
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Questions & Answers

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 40m. Alternatively, you can take a bus from Gulf St @ George St to Chicago Bus Station via Union Ave @ Union Station, New Haven Union Station, Port Authority Bus Terminal, and New York Midtown in around 25h 8m.

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