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

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There are 11 ways to get from Chicago to New Canaan by plane, train, bus (Flixbus, Greyhound), train (Amtrak), 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 28m
    $202–591

  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 29m
    $112–523

  3. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2641 / ...
    2. Take the bus from Port Authority Bus Terminal to Stamford Bus Stopbus bus Greyhound US0240
    20h 45m
    $156–258

  4. 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 31m
    $326–1,185

  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 48m
    $232–691

  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 New Canaantrain train
    6h 55m
    $338–893

  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
    6h 59m
    $196–1,444

  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 27m
    $134–1,154

  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 53m
    $180–1,069

  11. Bus, train

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore to Port Authority Bus Terminalbus bus
    3. Take the train from Grand Central Terminal to Stamfordtrain train
    24h 16m
    $176–340

Chicago to New Canaan by bus, foot, and train

Calendar14Weekly Services
Duration20h 45mAverage Duration
Ticket$156Cheapest Price
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Questions & Answers

Map of how to get from Chicago to New Canaan.ExpandLaunch map view
  • Distance: 777.7 mi
  • Duration: 6h 28m

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

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 20h 45m. Alternatively, 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 31m.

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