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

Find Transport to Chicago

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There are 10 ways to get from North Haven to Chicago by train, plane, train (Amtrak), bus (Greyhound, Flixbus), or car

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 Bradley International Airport, fly to Chicago Midway International Airport

    best
    1. Take the train from Wallingford Amtrak to Windsor Lockstrain train
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    6h 33m
    $104–491

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

    cheapest
    1. Take the train from Wallingford Amtrak to Windsor Lockstrain train
    2. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    7h 3m
    $89–401

  3. Train (Amtrak)

    1. Take the train from Wallingford Amtrak to Springfieldtrain train Amtrak Hartford Line / ...
    2. Take the train from Springfield to Chicago Union Stationtrain train Lake Shore Limited
    23h 13m
    $529–848

  4. Bus

    1. Take the bus from New Haven Bus Stop to Port Authority Bus Terminalbus bus Greyhound US0230 / ...
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    25h 41m
    $155–256

  5. Drive  864.5 mi

    1. Drive from North Haven to Chicagocar car 864.5 mi
    14h 38m
    $158–228

  6. 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 16m
    $115–422

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

    1. Take the train from New Haven to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    7h 47m
    $226–698

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

    1. Take the train from New Haven to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    8h 4m
    $156–598

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

    1. Take the train from New Haven to Stamfordtrain train
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    9h 20m
    $118–1,219

  10. Train via New York (Amtrak)

    1. Take the train from New Haven to Ny Moynihan Train Hall At Penn Stationtrain train Northeast Regional / ...
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    23h 41m
    $520–1,457

North Haven to Chicago by bus and train (Amtrak)

Calendar7Weekly Services
Duration23h 13mAverage Duration
Ticket$529Cheapest Price
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Comparing Your Travel Options

Map of how to get from North Haven to Chicago.ExpandLaunch map view
  • Distance: 830.9 mi
  • Duration: 6h 33m

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

You can take a bus from Washington Ave @ opp Walgreens to Chicago Union Station via Center St @ N Colony St, Wallingford Amtrak, and Springfield in around 23h 13m. Alternatively, you can take a bus from Washington Ave @ Walgreens to Chicago Bus Station via Temple St @ New Haven Green, Temple St @ Chapel St, Union Ave @ Cinque Grn, New Haven Bus Stop, Port Authority Bus Terminal, and New York Midtown in around 25h 41m.

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