Rome2Rio

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

Find Transport to Chicago

See all options

There are 10 ways to get from West Haven to Chicago by plane, train (Amtrak), bus (Greyhound, Flixbus), 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 40m
    $114–411

  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
    6h
    $94–408

  3. 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
    $517–1,433

  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 / ...
    23h 46m
    $152–249

  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 30m
    $109–498

  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 25m
    $223–690

  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 42m
    $153–590

  9. 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
    $534–853

  10. Train, bus

    1. Take the train from West Haven 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 36m
    $177–286

West Haven to Chicago by train (Amtrak)

Calendar10Weekly Trains
Duration22h 9mAverage Duration
Ticket$517Cheapest Price
See schedules

Comparing Your Travel Options

Map of how to get from West Haven to Chicago.ExpandLaunch map view
  • Distance: 793.9 mi
  • Duration: 3h 40m

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) 5 times a week. Alternatively, you can take a train from New Haven to Chicago Union Station via Ny Moynihan Train Hall At Penn Station in around 22h 9m.

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

Booking & Getting There