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

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There are 9 ways to get from Chicago to Brewster by plane, train, bus, train (Amtrak), car, or shuttle

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 Brewstertrain train
    5h 56m
    $220–585

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

    cheapest
    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
    6h 51m
    $110–525

  3. Bus, train

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2641 / ...
    2. Take the train from White Plains to Brewstertrain train Harlem
    20h 21m
    $149–245

  4. Train

    1. Take the train from Chicago Union Station to Ny Moynihan Train Hall At Penn Stationtrain train Lake Shore Limited / ...
    2. Take the train from Grand Central Terminal to Brewstertrain train Harlem
    22h 24m
    $314–653

  5. Drive 824.7 mi

    1. Drive from Chicago to Brewstercar car 824.7 mi
    13h 40m
    $151–218

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

    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 Brewstertrain train
    6h 17m
    $150–685

  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 Grand Central Terminal to Brewstertrain train
    6h 29m
    $342–896

  8. Fly Chicago O'Hare International Airport to Newark Liberty International Airport, shuttle, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane plane ORD - EWR
    2. Take a shuttle bus from Newark Airport Terminal B to Grand Centralshuttle bus
    3. Take the train from Grand Central Terminal to Brewstertrain train
    7h 4m
    $182–928

  9. Bus, train via Baltimore

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore Downtown Bus Station to Port Authority Bus Terminalbus bus
    3. Take the train from Grand Central Terminal to Brewstertrain train
    23h 36m
    $176–365

Chicago to Brewster by bus and train

Calendar7Weekly Services
Duration20h 21mAverage Duration
Ticket$149Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Brewster.ExpandLaunch map view
  • Distance: 788.6 mi
  • Duration: 5h 56m

What companies run services between Chicago, IL, USA and Brewster, NY, USA?

You can take a train from Chicago Union Station to Brewster via Ny Moynihan Train Hall At Penn Station, W 42 St/9 Av, E 42 St/Madison Av, and Grand Central Terminal in around 22h 24m.

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