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

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There are 10 ways to get from Chicago to Stamford 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
    5h 34m
    $166–580

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

    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 Main St @ Atlantic Stbus bus
    6h 39m
    $102–562

  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
    19h 51m
    $143–236

  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 / ...
    21h 38m
    $324–1,173

  5. Drive 818.4 mi

    1. Drive from Chicago to Stamfordcar car 818.4 mi
    13h 46m
    $150–216

  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
    5h 55m
    $216–680

  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
    6h 8m
    $338–891

  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 10m
    $180–1,983

  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
    7h 34m
    $128–1,143

  10. Bus, train

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore Downtown Bus Station to Port Authority Bus Terminalbus bus
    3. Take the train from Grand Central Terminal to Stamfordtrain train
    23h 17m
    $177–374

Chicago to Stamford by bus and foot

Calendar7Weekly Services
Duration19h 51mAverage Duration
Ticket$143Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Stamford.ExpandLaunch map view
  • Distance: 769.7 mi
  • Duration: 5h 34m

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

You can take a bus from Chicago Bus Station to Stamford Bus Stop via New York Midtown and Port Authority Bus Terminal in around 19h 51m. Alternatively, you can take a train from Chicago Union Station to Stamford Amtrak Station via Ny Moynihan Train Hall At Penn Station in around 21h 38m.

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