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How to get fromChicago to New Canaanby plane, train, train (Amtrak), bus (Flixbus, Greyhound), car, or bus

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There are 11 ways to get from Chicago to New Canaan by plane, train, train (Amtrak), bus (Flixbus, Greyhound), 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 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 Stamfordtrain train
    6h 35m
    $222–691

  2. Fly Chicago O'Hare International Airport to Westchester County Airport, line 971 bus, train

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the bus from Main St @ South Broadway to Stamford Transportation Center @ Bay Abus bus
    3. Take the train from Stamford to New Canaantrain train
    7h 38m
    $92–453

  3. Train (Amtrak)

    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 Ny Moynihan Train Hall At Penn Station to Stamford Amtrak Stationtrain train Northeast Regional / ...
    22h 34m
    $262–1,164

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2640 / ...
    2. Take the bus from Port Authority Bus Terminal to Stamford Bus Stopbus bus Greyhound US0240
    23h 52m
    $162–244

  5. Drive  826.3 mi

    1. Drive from Chicago to New Canaancar car 826.3 mi
    14h
    $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 Stamfordtrain train
    6h 52m
    $152–591

  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 Stamfordtrain train
    7h 3m
    $344–902

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane plane ORD - EWR
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Stamford Amtrak Stationtrain train
    7h 2m
    $158–1,444

  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 Stamfordtrain train
    8h 28m
    $150–1,349

  10. Fly Chicago Midway International Airport to Philadelphia International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Philadelphia International Airport (PHL)plane plane MDW - PHL
    2. Take the train from 30th Street Station to Stamford Amtrak Stationtrain train
    8h 55m
    $180–1,040

  11. Bus, train

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore to New Yorkbus bus
    3. Take the train from Grand Central Terminal to Stamfordtrain train
    24h 54m
    $187–311

Chicago to New Canaan by train (Amtrak)

Calendar10Weekly Trains
Duration22h 34mAverage Duration
Ticket$262Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to New Canaan.ExpandLaunch map view
  • Distance: 777.7 mi
  • Duration: 6h 35m

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

You can take a train from Chicago Union Station to New Canaan via Ny Moynihan Train Hall At Penn Station, Stamford Amtrak Station, and Stamford in around 22h 34m. Alternatively, you can take a bus from Chicago Bus Station to New Canaan via New York Midtown, Port Authority Bus Terminal, Stamford Bus Stop, and Stamford in around 23h 52m.

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