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How to get fromNew Canaan to Chicagoby train, plane, train (Amtrak), bus (Greyhound, Flixbus), car, or bus

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There are 11 ways to get from New Canaan to Chicago by train, plane, 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. Train to Laguardia Airport, fly to Chicago Midway International Airport

    best
    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
    5h 58m
    $221–690

  2. Train, train to Bradley International Airport, fly to Chicago Midway International Airport

    cheapest
    1. Take the train from Stamford to New Haventrain train
    2. Take the train from New Haven to Windsor Lockstrain train
    3. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    8h 17m
    $110–1,098

  3. Train (Amtrak)

    1. Take the train from Stamford 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 / ...
    22h 14m
    $254–1,210

  4. Bus

    1. Take the bus from Stamford Bus Stop to Port Authority Bus Terminalbus bus Greyhound US0240
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    24h 38m
    $162–250

  5. Drive  827.1 mi

    1. Drive from New Canaan to Chicagocar car 827.1 mi
    13h 56m
    $151–218

  6. 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 16m
    $151–590

  7. 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
    6h 51m
    $343–901

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

    1. Take the train from Stamford Amtrak Station to Ny Moynihan Train Hall At Penn Stationtrain train
    2. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    6h 47m
    $157–1,443

  9. Train, line 971 bus to Westchester County Airport, fly to Chicago O'Hare International Airport

    1. Take the train from New Canaan to Stamfordtrain train
    2. Take the bus from Stamford Transportation Center @ Bay A to South Broadway @ Main Stbus bus
    3. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    7h 16m
    $112–622

  10. Train to Laguardia Airport, fly to General Mitchell International Airport, train

    1. Take the train from Stamford to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to General Mitchell International Airport (MKE)plane plane LGA - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain train
    8h 33m
    $182–904

  11. Train, bus

    1. Take the train from Stamford 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
    26h 10m
    $175–286

New Canaan to Chicago by train (Amtrak)

Calendar10Weekly Trains
Duration22h 14mAverage Duration
Ticket$254Cheapest Price
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Comparing Your Travel Options

Map of how to get from New Canaan to Chicago.ExpandLaunch map view
  • Distance: 778 mi
  • Duration: 5h 58m

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

You can take a train from New Canaan to Chicago Union Station via Stamford, Stamford Amtrak Station, and Ny Moynihan Train Hall At Penn Station in around 22h 14m. Alternatively, you can take a train from New Canaan to Chicago Bus Station via Stamford, Stamford Bus Stop, Port Authority Bus Terminal, and New York Midtown in around 24h 38m.

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