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

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There are 9 ways to get from Brewster 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 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
    5h 49m
    $219–585

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

    cheapest
    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
    6h 45m
    $111–574

  3. 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 / ...
    21h 12m
    $144–253

  4. Train

    1. Take the train from Brewster to Grand Central Terminaltrain train Harlem
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    22h 30m
    $308–681

  5. Drive 824.5 mi

    1. Drive from Brewster to Chicagocar car 824.5 mi
    13h 39m
    $151–218

  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
    6h 10m
    $149–685

  7. Train to John F. Kennedy International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Brewster to Grand Central Terminaltrain train
    2. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    6h 38m
    $341–896

  8. Train, bus to Newark Liberty International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Brewster to Grand Central Terminaltrain train
    2. Take the bus from Bryant Park to Terminal Bbus bus
    3. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    7h 5m
    $162–903

  9. Train, bus via Baltimore

    1. Take the train from Brewster to Grand Central Terminaltrain train
    2. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus bus
    3. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus
    25h 12m
    $173–371

Brewster to Chicago by train and bus

Calendar7Weekly Services
Duration21h 12mAverage Duration
Ticket$144Cheapest Price
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Questions & Answers

Map of how to get from Brewster to Chicago.ExpandLaunch map view
  • Distance: 788.9 mi
  • Duration: 5h 49m

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

You can take a train from Brewster to Chicago Union Station via Grand Central Terminal, 5 Av/W 41 St, 7 Av/ W 36 St, and Ny Moynihan Train Hall At Penn Station in around 22h 30m.

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Train operators
Bus operators

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