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How to get fromConnecticut to Winnetkaby plane, train, train (Amtrak), bus (Greyhound, Flixbus), car, or bus

Find Transport to Winnetka

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There are 10 ways to get from Connecticut to Winnetka by plane, train, train (Amtrak), bus (Greyhound, Flixbus), car, or bus

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 Bradley International Airport to Chicago Midway International Airport, train

    best
    1. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    2. Take the train from Chicago OTC to Winnetkatrain train
    5h 52m
    $88–443

  2. Fly Bradley International Airport to Chicago O'Hare International Airport

    cheapest
    1. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    6h 5m
    $68–354

  3. Train (Amtrak)

    1. Take the train from Bridgeport Amtrak Station to Ny Moynihan Train Hall At Penn Stationtrain train Northeast Regional / ...
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    23h 13m
    $251–642

  4. Bus

    1. Take the bus from Bridgeport Bus Stop to Port Authority Bus Terminalbus bus Greyhound US0255s
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    26h 2m
    $157–243

  5. Drive  857.6 mi

    1. Drive from Bridgeport to Winnetkacar car 857.6 mi
    14h 38m
    $157–227

  6. Train to Laguardia Airport, fly to Chicago Midway International Airport

    1. Take the train from Stamford to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    6h 50m
    $219–684

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

    1. Take the train from Stamford to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    6h 54m
    $149–585

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

    1. Take the train from Stamford 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
    7h 30m
    $341–896

  9. Line 971 bus to Westchester County Airport, fly to Chicago O'Hare International Airport, train

    1. Take the bus from Main St @ Atlantic St to South Broadway @ Main Stbus bus
    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
    7h 34m
    $106–568

  10. Train, bus

    1. Take the train from Bridgeport 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
    27h 27m
    $171–290

Connecticut to Winnetka by train and bus (Amtrak)

Calendar10Weekly Services
Duration23h 13mAverage Duration
Ticket$251Cheapest Price
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Comparing Your Travel Options

Map of how to get from Connecticut to Winnetka.ExpandLaunch map view
  • Distance: 817 mi
  • Duration: 5h 52m

What companies run services between Connecticut, USA and Winnetka, IL, USA?

You can take a train from Bridgeport Amtrak Station to Winnetka via Ny Moynihan Train Hall At Penn Station, Chicago Union Station, Clinton & Quincy, Washington & Canal, and Chicago OTC in around 23h 13m. Alternatively, you can take a bus from Bridgeport Bus Stop to Green Bay Rd & Pine St via Port Authority Bus Terminal, New York Midtown, Chicago Bus Station, Jefferson & Harrison, Washington & State, Washington & Wabash, Rogers & Paulina, and Howard CTA Station in around 26h 2m.

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