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How to get fromNew York to Winnetkaby subway, bus, plane, train, train (Amtrak), bus (Greyhound, Amtrak), car, or bus (Flixbus)

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There are 11 ways to get from New York to Winnetka by subway, bus, plane, train, train (Amtrak), bus (Greyhound, Amtrak), car, or bus (Flixbus)

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Line 4 subway, bus to Laguardia Airport, fly to Chicago Midway International Airport, train

    best
    1. Take the subway from 14 St-Union Sq to 125th Streetsubway subway
    2. Take the bus from E 125 St/Lexington Av to Laguardia Rd/94 Stbus bus
    3. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    4. Take the train from Chicago OTC to Winnetkatrain train
    6h 2m
    $212–671

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

    cheapest
    1. Take the train from Grand Central Terminal to White Plainstrain train
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    3. Take the train from Clybourn to Winnetkatrain train
    8h 1m
    $118–578

  3. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    20h 50m
    $260–560

  4. Bus via Toledo

    1. Take the bus from Port Authority Bus Terminal to Toledo Bus Stopbus bus Greyhound US0420
    2. Take the bus from Toledo to Chicago Union Stationbus bus Amtrak Thruway Connecting Service
    22h 50m
    $176–271

  5. Drive  806.4 mi

    1. Drive from New York to Winnetkacar car 806.4 mi
    13h 37m
    $148–213

  6. Line 4 subway, bus to Laguardia Airport, fly to Chicago O'Hare International Airport, train

    1. Take the subway from 14 St-Union Sq to 125th Streetsubway subway
    2. Take the bus from E 125 St/Lexington Av to Laguardia Rd/94 Stbus bus
    3. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    4. Take the train from Clybourn to Winnetkatrain train
    6h 9m
    $142–572

  7. Fly Newark Liberty International Airport to Chicago O'Hare International Airport

    1. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    6h 4m
    $147–888

  8. Fly John F. Kennedy International Airport to Chicago O'Hare International Airport

    1. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    6h 13m
    $330–879

  9. Fly Newark Liberty International Airport to General Mitchell International Airport, train

    1. Fly from Newark Liberty International Airport (EWR) to General Mitchell International Airport (MKE)plane plane EWR - MKE
    2. Take the train from Milwaukee to Glenview Amtrak Stationtrain train
    8h 2m
    $592–884

  10. Fly Laguardia Airport to General Mitchell International Airport, train

    1. Fly from Laguardia Airport (LGA) to General Mitchell International Airport (MKE)plane plane LGA - MKE
    2. Take the train from Milwaukee to Glenview Amtrak Stationtrain train
    8h 13m
    $167–818

  11. Bus (Flixbus)

    1. Take the bus from New York City Chinatown to Chicago Bus Stationbus bus FlixBus N2640
    23h 26m
    $156–232

New York to Winnetka by train and bus (Amtrak)

Calendar10Weekly Services
Duration20h 50mAverage Duration
Ticket$260Cheapest Price
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Questions & Answers

Map of how to get from New York to Winnetka.ExpandLaunch map view
  • Distance: 764.4 mi
  • Duration: 6h 2m

What companies run services between New York, NY, USA and Winnetka, IL, USA?

Amtrak operates a train from Ny Moynihan Train Hall At Penn Station to Chicago Union Station once daily. Tickets cost $250–550 and the journey takes 19h 32m. Alternatively, you can take a bus from Port Authority Bus Terminal to Winnetka via Toledo, Chicago Union Station, Clinton & Quincy, Washington & Canal, and Chicago OTC in around 22h 50m.

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