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How to get fromBrookfield to Chicagoby train, plane, bus, or car

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There are 8 ways to get from Brookfield to Chicago by train, plane, bus, 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 to Laguardia Airport, fly to Chicago Midway International Airport

    best
    1. Take the train from Brewster to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    7h 52m
    $199–585

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

    cheapest
    1. Take the train from South Norwalk 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
    10h 50m
    $102–395

  3. Bus, train

    1. Take the bus from Cousins Cafe to Poughkeepsie Train Stationbus bus E
    2. Take the train from Poughkeepsie Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    20h 47m
    $337–667

  4. Train, bus

    1. Take the train from Brewster to White Plainstrain train Harlem
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    22h 48m
    $155–263

  5. Drive 840.3 mi

    1. Drive from Brookfield to Chicagocar car 840.3 mi
    13h 57m
    $154–222

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

    1. Take the train from Brewster to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    8h 13m
    $229–685

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

    1. Take the train from Brewster to White Plainstrain train
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    8h 52m
    $106–474

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

    1. Take the train from South Norwalk 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
    10h 17m
    $112–455

Brookfield to Chicago by bus and train

Calendar21Weekly Services
Duration22h 48mAverage Duration
Ticket$155Cheapest Price
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Questions & Answers

Map of how to get from Brookfield to Chicago.ExpandLaunch map view
  • Distance: 807.2 mi
  • Duration: 7h 52m

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

There is no direct connection from Brookfield to Chicago. However, you can take the line 9 bus to PC Richards, walk to Federal Road Park & Ride, take the line 12 bus to Brewster Village Mta, walk to Brewster, take the train to 125th Street - Harlem, walk to E 125 St/Lexington Av, take the bus to Laguardia Rd/94 St, walk to New-York-La-Guardia-Airport-LGA airport, fly to Chicago Midway International Airport (MDW), walk to Midway, then take the subway to Harold Washington Library. Alternatively, you can take a vehicle from Brookfield to Chicago Union Station via Cousins Cafe, Poughkeepsie Train Station, and Poughkeepsie Amtrak Station in around 20h 47m.

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