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

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There are 11 ways to get from Darien 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 Darien to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    5h 28m
    $216–681

  2. Line 971 bus to Westchester County Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the bus from Stamford Transportation Center @ Bay A to South Broadway @ Main Stbus bus
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    7h 9m
    $112–621

  3. Train

    1. Take the train from Darien to 125th Street - Harlemtrain train
    2. Take the train from 125th Street - Harlem to Croton-Harmontrain train
    3. Take the train from Croton-Harmon Amtrak Station to Chicago Union Stationtrain train
    21h 52m
    $521–835

  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 31m
    $152–250

  5. Drive  822.5 mi

    1. Drive from Darien to Chicagocar car 822.5 mi
    13h 48m
    $151–217

  6. Train to Laguardia Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Darien to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    5h 45m
    $146–581

  7. Train to John F. Kennedy International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Darien 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 20m
    $338–892

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

    1. Take the train from Darien to Grand Central Terminaltrain train
    2. Take the bus from Bryant Park to Terminal Bbus bus
    3. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    6h 41m
    $159–899

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

    1. Take the train from Darien 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 42m
    $121–521

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

    1. Take the train from Darien 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 2m
    $201–915

  11. Train, bus

    1. Take the train from Darien 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 39m
    $170–277

Darien to Chicago by train

Calendar7Weekly Trains
Duration21h 52mAverage Duration
Ticket$521Cheapest Price
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Comparing Your Travel Options

Map of how to get from Darien to Chicago.ExpandLaunch map view
  • Distance: 774.6 mi
  • Duration: 5h 28m

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

You can take a train from Darien to Chicago Union Station via 125th Street - Harlem and Croton-Harmon Amtrak Station in around 21h 52m. Alternatively, you can take a train from Darien to Chicago Bus Station via Stamford, Stamford Bus Stop, Port Authority Bus Terminal, and New York Midtown in around 24h 31m.

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Want to know more about travelling around United States

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