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How to get fromDarien to Chicago Loopby train, plane, train (Amtrak), bus, car or bus (Flixbus)

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There are 11 ways to get from Darien to Chicago Loop by train, plane, train (Amtrak), bus, car, or bus (Flixbus)

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 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
    $65–309

  2. 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 50m
    $271–584

  3. 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 1m
    $192–388

  4. Drive 823.3 mi

    1. Drive from Darien to Chicago Loopcar car 823.3 mi
    13h 49m
    $151–217

  5. Train to Laguardia Airport, fly to Chicago Midway International Airport

    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 40m
    $105–529

  6. 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 14m
    $67–291

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

    1. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    7h 9m
    $453–622

  8. 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
    7h 19m
    $71–315

  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 52m
    $121–835

  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 8m
    $188–938

  11. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640
    25h 41m
    $129–236

Darien to Chicago Loop by train

Calendar7Weekly Trains
Duration21h 50mAverage Duration
Ticket$271Cheapest Price
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Questions & Answers

What companies run services between Darien, CT, USA and Chicago Loop, 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 50m. Alternatively, American Airlines and Delta fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD) every 2 hours.

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