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How to get fromWestbrook to Chicagoby train, plane, bus, train (Amtrak), or car

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There are 11 ways to get from Westbrook to Chicago by train, plane, 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. Train, train to Laguardia Airport, fly to Chicago Midway International Airport

    best
    1. Take the train from Westbrook to New Haventrain train
    2. Take the train from New Haven to 125th Street - Harlemtrain train
    3. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    7h 27m
    $209–598

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

    cheapest
    1. Take the train from Westbrook to New Haventrain train
    2. Take the train from New Haven to Windsor Lockstrain train
    3. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    7h 30m
    $89–370

  3. Train, bus

    1. Take the train from Westbrook to New Haventrain train
    2. Take the bus from New Haven Union Station to Port Authority Bus Terminalbus bus
    3. Take the bus from New York Midtown to Chicago Bus Stationbus bus
    21h 35m
    $157–297

  4. Train via New York

    1. Take the train from Westbrook to New Haventrain train
    2. Take the train from New Haven to Ny Moynihan Train Hall At Penn Stationtrain train
    3. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train
    23h 25m
    $333–1,257

  5. Drive 884 mi

    1. Drive from Westbrook to Chicagocar car 884 mi
    15h
    $162–233

  6. Train, train to Bradley International Airport, fly to Chicago Midway International Airport

    1. Take the train from Westbrook to New Haventrain train
    2. Take the train from New Haven to Windsor Lockstrain train
    3. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    6h 56m
    $99–430

  7. Train to Tweed-New Haven Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Westbrook to New Haventrain train
    2. Fly from Tweed-New Haven Airport (HVN) to Chicago O'Hare International Airport (ORD)plane plane HVN - ORD
    6h 8m
    $109–345

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

    1. Take the train from Westbrook to New Haventrain train
    2. Take the train from New Haven to Stamfordtrain train
    3. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    8h 56m
    $111–1,069

  9. Train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport

    1. Take the train from New London to Providencetrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    8h 4m
    $103–443

  10. Train

    1. Take the train from Westbrook to New Haventrain train
    2. Take the train from New Haven to Springfieldtrain train
    3. Take the train from Springfield to Chicago Union Stationtrain train
    23h 41m
    $326–702

  11. Train, bus via Baltimore

    1. Take the train from Westbrook to New Haventrain train
    2. Take the bus from New Haven Union Station to Port Authority Bus Terminalbus bus
    3. Take the bus from Port Authority Bus Terminal to Baltimorebus bus
    4. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus
    27h 17m
    $162–337

Westbrook to Chicago by train, bus, and foot

Calendar22Weekly Services
Duration21h 35mAverage Duration
Ticket$157Cheapest Price
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Questions & Answers

Map of how to get from Westbrook to Chicago.ExpandLaunch map view
  • Distance: 838.2 mi
  • Duration: 7h 27m

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

You can take a train from Westbrook to Chicago Union Station via New Haven and Ny Moynihan Train Hall At Penn Station in around 23h 25m.

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Train operators
Bus operators

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