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How to get fromChicago to Westbrookby plane, train, bus, train (Amtrak), or car

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There are 12 ways to get from Chicago to Westbrook by plane, train, bus, train (Amtrak), 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. Fly Chicago Midway International Airport to Laguardia Airport, train

    best
    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from 125th Street - Harlem to New Haventrain train
    3. Take the train from New Haven to Westbrooktrain train
    7h 48m
    $208–599

  2. Fly Chicago O'Hare International Airport to Bradley International Airport, train

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane plane ORD - BDL
    2. Take the train from Windsor Locks to New Haventrain train
    3. Take the train from New Haven to Westbrooktrain train
    7h 49m
    $98–441

  3. Bus, train

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus
    2. Take the bus from Port Authority Bus Terminal to New Haven Union Stationbus bus
    3. Take the train from New Haven to Westbrooktrain train
    21h 2m
    $163–292

  4. Train

    1. Take the train from Chicago Union Station to Springfieldtrain train
    2. Take the train from Springfield to New Haventrain train
    3. Take the train from New Haven to Westbrooktrain train
    22h 49m
    $325–658

  5. Drive 883.8 mi

    1. Drive from Chicago to Westbrookcar car 883.8 mi
    15h 2m
    $162–233

  6. Fly Chicago Midway International Airport to Bradley International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    2. Take the train from Windsor Locks to New Haventrain train
    3. Take the train from New Haven to Westbrooktrain train
    7h 18m
    $124–551

  7. Fly Chicago O'Hare International Airport to John F. Kennedy International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK)plane plane ORD - JFK
    2. Take the train from Ny Moynihan Train Hall At Penn Station to New Haventrain train
    3. Take the train from New Haven to Westbrooktrain train
    8h 9m
    $348–1,482

  8. Fly Chicago O'Hare International Airport to Westchester County Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the train from Stamford to New Haventrain train
    3. Take the train from New Haven to Westbrooktrain train
    9h 17m
    $120–1,120

  9. Fly Chicago Midway International Airport to Theodore Francis Green State Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Theodore Francis Green State Airport (PVD)plane plane MDW - PVD
    2. Take the train from Providence to New Londontrain train
    8h 11m
    $108–453

  10. Fly Chicago O'Hare International Airport to Tweed-New Haven Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Tweed-New Haven Airport (HVN)plane plane ORD - HVN
    2. Take the train from New Haven to Westbrooktrain train
    7h 45m
    $150–489

  11. Train via New York

    1. Take the train from Chicago Union Station to Ny Moynihan Train Hall At Penn Stationtrain train
    2. Take the train from Ny Moynihan Train Hall At Penn Station to New Haventrain train
    3. Take the train from New Haven to Westbrooktrain train
    23h 41m
    $335–1,240

  12. Bus, train via Baltimore

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore to Port Authority Bus Terminalbus bus
    3. Take the bus from Port Authority Bus Terminal to New Haven Union Stationbus bus
    4. Take the train from New Haven to Westbrooktrain train
    25h 33m
    $168–339

Chicago to Westbrook by bus, foot, and train

Calendar23Weekly Services
Duration21h 2mAverage Duration
Ticket$163Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Westbrook.ExpandLaunch map view
  • Distance: 837.9 mi
  • Duration: 7h 48m

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

You can take a train from Chicago Union Station to Westbrook via Springfield and New Haven in around 22h 49m.

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