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

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There are 10 ways to get from Milford to Chicago by train, plane, bus (Greyhound, Flixbus), 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. 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 15m
    $172–588

  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 18m
    $84–373

  3. 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 N2641 / ...
    21h 38m
    $143–278

  4. 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
    $327–642

  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 36m
    $222–688

  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 44m
    $94–433

  8. 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 52m
    $102–469

  9. 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 21m
    $181–507

  10. 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 38m
    $175–384

Milford to Chicago by bus and foot

Calendar15Weekly Services
Duration21h 38mAverage Duration
Ticket$143Cheapest Price
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Questions & Answers

Map of how to get from Milford to Chicago.ExpandLaunch map view
  • Distance: 800.3 mi
  • Duration: 6h 15m

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

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 21h 38m. Alternatively, you can take a train from Milford to Chicago Union Station via 125th Street - Harlem and Croton-Harmon Amtrak Station in around 22h 41m.

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