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

Find Transport to Darien

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There are 10 ways to get from Chicago to Darien 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 O'Hare International Airport to Laguardia Airport, train

    best
    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 Darientrain train
    5h 44m
    $146–581

  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 Stamford Transportation Center @ Bay Abus bus
    6h 59m
    $96–482

  3. Train

    1. Take the train from Chicago Union Station to Croton-Harmon Amtrak Stationtrain train
    2. Take the train from Croton-Harmon to 125th Street - Harlemtrain train
    3. Take the train from 125th Street - Harlem to Darientrain train
    21h 45m
    $246–568

  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 39m
    $156–235

  5. Drive  822.5 mi

    1. Drive from Chicago to Dariencar car 822.5 mi
    13h 50m
    $151–217

  6. Fly Chicago Midway International Airport to Laguardia Airport, train

    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 Darientrain train
    5h 30m
    $216–681

  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 Darientrain train
    6h 3m
    $338–892

  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 32m
    $156–1,443

  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 Darientrain train
    7h 34m
    $136–704

  10. 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 Darientrain train
    23h 53m
    $180–298

Chicago to Darien by train

Calendar7Weekly Trains
Duration21h 45mAverage Duration
Ticket$246Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Darien.ExpandLaunch map view
  • Distance: 789.7 mi
  • Duration: 5h 44m

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

You can take a train from Chicago Union Station to Darien via Croton-Harmon and 125th Street - Harlem in around 21h 45m. Alternatively, you can take a bus from Chicago Bus Station to Boston Post Rd @ opp Mansfield Ave via New York Midtown, Port Authority Bus Terminal, Stamford Bus Stop, and Stamford Transportation Center @ Bay E in around 23h 39m.

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