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

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There are 11 ways to get from New Haven to Chicago by train, plane, bus (Greyhound, Flixbus), train (Amtrak), car, or bus (Greyhound)

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 New Haven to Windsor Lockstrain train
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    5h 23m
    $93–419

  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
    5h 57m
    $83–359

  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 / ...
    19h 56m
    $152–281

  4. Train (Amtrak)

    1. Take the train from New Haven to Springfieldtrain train Amtrak Hartford Line / ...
    2. Take the train from Springfield to Chicago Union Stationtrain train Lake Shore Limited
    22h 8m
    $320–690

  5. Drive 857.3 mi

    1. Drive from New Haven to Chicagocar car 857.3 mi
    14h 32m
    $157–226

  6. 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
    6h 28m
    $203–591

  7. 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
    6h 49m
    $233–691

  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
    4h 59m
    $104–338

  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
    8h 5m
    $105–1,015

  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 / ...
    22h 9m
    $327–1,233

  11. Bus via Baltimore

    1. Take the bus from New Haven Union Station to Port Authority Bus Terminalbus bus
    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 19m
    $177–401

New Haven to Chicago by bus and foot

Calendar15Weekly Services
Duration19h 56mAverage Duration
Ticket$152Cheapest Price
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Questions & Answers

Map of how to get from New Haven to Chicago.ExpandLaunch map view
  • Distance: 836.1 mi
  • Duration: 5h 23m

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

You can take a bus from New Haven Union Station to Chicago Bus Station via Port Authority Bus Terminal and New York Midtown in around 19h 56m. Alternatively, you can take a train from New Haven to Chicago Union Station via Springfield in around 22h 8m.

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