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How to get fromChicago to Brookfieldby subway, plane, train, bus, or car

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There are 9 ways to get from Chicago to Brookfield by subway, plane, train, 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. Subway to Chicago Midway International Airport, fly to Laguardia Airport, train, line 7 bus

    best
    1. Take the subway from Adams/Wabash to Midwaysubway subway
    2. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    3. Take the train from 125th Street - Harlem to South Norwalktrain train
    4. Take the train from South Norwalk to Danburytrain train
    5. Take the bus from White Street and Patriot Drive to Brookfield Village Barbershopbus bus
    8h 33m

  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 South Norwalktrain train
    10h 52m
    $112–465

  3. Train, bus

    1. Take the train from Chicago Union Station to Poughkeepsie Amtrak Stationtrain train Lake Shore Limited
    2. Take the bus from Poughkeepsie Train Station to Chamber of Commercebus bus E
    21h 19m
    $351–656

  4. Bus, train

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Stamford Amtrak Stationtrain train
    3. Take the bus from Norwalk Wheels Hub to Pulse Pointbus bus 15
    22h 37m

  5. Drive 840.8 mi

    1. Drive from Chicago to Brookfieldcar car 840.8 mi
    13h 59m
    $154–222

  6. Fly Chicago O'Hare International Airport to Laguardia Airport, train, line 7 bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    2. Take the train from 125th Street - Harlem to South Norwalktrain train
    3. Take the train from South Norwalk to Danburytrain train
    4. Take the bus from White Street and Patriot Drive to Brookfield Village Barbershopbus bus
    8h 53m

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

    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 Jamaica to Grand Central Terminaltrain train
    3. Take the train from Grand Central Terminal to South Norwalktrain train
    4. Take the train from South Norwalk to Danburytrain train
    5. Take the bus from White Street and Patriot Drive to Brookfield Village Barbershopbus bus
    9h 6m

  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 White Plains to Brewstertrain train
    9h 12m
    $116–525

  9. 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 South Norwalktrain train
    10h 22m
    $138–575

Chicago Midway International Airport (MDW) to Laguardia Airport (LGA) flights

Calendar54Weekly Planes
Duration2h 10mAverage Duration
Ticket$132Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Brookfield.ExpandLaunch map view
  • Distance: 809 mi
  • Duration: 8h 33m

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

There is no direct connection from Chicago to Brookfield. However, you can take the subway to Midway, walk to Chicago-Midway-Airport-MDW airport, fly to Laguardia Airport (LGA), walk to Lga/Terminal B, take the bus to E 125 St/Lexington Av, walk to 125th Street - Harlem, take the train to South Norwalk, take the train to Danbury, walk to White Street and Patriot Drive, then take the line 9 bus to Brookfield Village Barbershop. Alternatively, you can take a train from Chicago Union Station to Brookfield via Poughkeepsie Amtrak Station, Poughkeepsie Train Station, and Chamber of Commerce in around 21h 19m.

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