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

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There are 10 ways to get from Stamford 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 O'Hare International Airport

    best
    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
    5h 42m
    $145–579

  2. Fly Westchester County Airport to Chicago O'Hare International Airport

    cheapest
    1. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    6h 17m
    $102–562

  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 / ...
    21h 21m
    $238–1,151

  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 / ...
    23h 21m
    $146–230

  5. Drive  818.3 mi

    1. Drive from Stamford to Chicagocar car 818.3 mi
    13h 43m
    $150–216

  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
    5h 33m
    $215–679

  7. 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
    5h 54m
    $151–1,434

  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
    6h 19m
    $337–890

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

    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
    7h 48m
    $103–1,019

  10. 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
    25h 45m
    $159–275

Stamford to Chicago by train (Amtrak)

Calendar10Weekly Trains
Duration21h 21mAverage Duration
Ticket$238Cheapest Price
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Comparing Your Travel Options

Map of how to get from Stamford to Chicago.ExpandLaunch map view
  • Distance: 785.5 mi
  • Duration: 5h 42m

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

You can take a train from Stamford Amtrak Station to Chicago Union Station via Ny Moynihan Train Hall At Penn Station in around 21h 21m. Alternatively, you can take a bus from Stamford Bus Stop to Chicago Bus Station via Port Authority Bus Terminal and New York Midtown in around 23h 21m.

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