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

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There are 10 ways to get from Chicago to Darien by plane, train, train (Amtrak), bus, car, or bus (Flixbus, Greyhound)

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)planeMDW - LGA
    2. Take the train from 125th Street - Harlem to Darientrain
    5h 21m
    $86–420

  2. Fly Chicago O'Hare International Airport to Laguardia Airport, train

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)planeORD - LGA
    2. Take the train from 125th Street - Harlem to Darientrain
    5h 41m
    $66–290

  3. Train

    1. Take the train from Chicago Union Station to Croton-Harmon Amtrak Stationtrain
    2. Take the train from Croton-Harmon to 125th Street - Harlemtrain
    3. Take the train from 125th Street - Harlem to Darientrain
    21h 40m
    $120–323

  4. Bus, train

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus
    2. Take the bus from Baltimore Downtown Bus Station to Port Authority Bus Terminalbus
    3. Take the train from Grand Central Terminal to Darientrain
    22h 58m
    $125–300

  5. Drive 822.5 mi

    1. Drive from Chicago to Dariencar822.5 mi
    13h 40m
    $151–217

  6. 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)planeORD - JFK
    2. Take the train from Grand Central Terminal to Darientrain
    5h 59m
    $828–1,042

  7. 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)planeORD - EWR
    2. Take the train from Newark Liberty International Airport to Stamford Amtrak Stationtrain
    7h 2m
    $70–516

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)planeORD - HPN
    2. Take the bus from Main St @ South Broadway to Stamford Transportation Center @ Bay Abus
    6h 57m
    $98–473

  9. Fly Chicago Midway International Airport to Bradley International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)planeMDW - BDL
    2. Take the train from Windsor Locks to New Haventrain
    3. Take the train from New Haven to Darientrain
    7h 27m
    $120–836

  10. Bus

    1. Take the bus from Chicago Bus Station to New York MidtownbusFlixBus N2640
    2. Take the bus from Port Authority Bus Terminal to Stamford Bus StopbusGreyhound US0240
    23h 39m
    $111–270

Chicago to Darien by train

Calendar7Weekly Trains
Duration21h 40mAverage Duration
Ticket$120Cheapest Price
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Questions & Answers

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 40m. 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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