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

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There are 11 ways to get from West Haven to Chicago by plane, bus (Greyhound, Flixbus), train (Amtrak), car, train, 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. Fly Tweed-New Haven Airport to Chicago O'Hare International Airport

    best
    1. Fly from Tweed-New Haven Airport (HVN) to Chicago O'Hare International Airport (ORD)plane plane HVN - ORD
    3h 38m
    $103–333

  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 59m
    $84–359

  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
    $152–280

  4. 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

  5. Drive 855.7 mi

    1. Drive from West Haven to Chicagocar car 855.7 mi
    14h 29m
    $157–226

  6. 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
    5h 25m
    $94–419

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

    1. Take the train from West Haven to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    6h 23m
    $203–590

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

    1. Take the train from West Haven to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    6h 44m
    $233–690

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

    1. Take the train from West Haven to Stamfordtrain train
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    8h
    $108–481

  10. 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 10m
    $310–641

  11. Train, bus

    1. Take the train from West Haven to Grand Central Terminaltrain train
    2. Take the bus from Port Authority Bus Terminal to Baltimorebus bus
    3. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus
    26h 5m
    $167–341

West Haven to Chicago by bus and foot

Calendar22Weekly Services
Duration19h 56mAverage Duration
Ticket$152Cheapest Price
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Questions & Answers

Map of how to get from West Haven to Chicago.ExpandLaunch map view
  • Distance: 793.9 mi
  • Duration: 3h 38m

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

Avelo Airlines flies from Tweed-New Haven Airport (HVN) to Chicago O'Hare International Airport (ORD) 4 times a week. Alternatively, 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.

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