Rome2Rio

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

Find Transport to Chicago

See all options

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 12m
    $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 23m
    $91–416

  3. 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 N2641 / ...
    22h 7m
    $130–218

  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 40m
    $267–592

  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 25m
    $152–588

  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 51m
    $101–476

  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 51m
    $117–579

  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 18m
    $181–577

  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
    26h 3m
    $150–299

Milford to Chicago by bus and foot

Calendar7Weekly Services
Duration22h 7mAverage Duration
Ticket$130Cheapest Price
See schedules

Questions & Answers

Map of how to get from Milford to Chicago.ExpandLaunch map view
  • Distance: 800.2 mi
  • Duration: 6h 12m

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

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 22h 7m. Alternatively, you can take a train from Milford to Chicago Union Station via 125th Street - Harlem and Croton-Harmon Amtrak Station in around 22h 40m.

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

More Questions & Answers