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

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There are 10 ways to get from Wilton 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 South Norwalk to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    6h 15m
    $152–591

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

    cheapest
    1. Take the train from Wilton to South Norwalktrain train
    2. Take the train from South Norwalk to Stamfordtrain train
    3. Take the bus from Stamford Transportation Center @ Bay A to South Broadway @ Main Stbus bus
    4. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    7h 53m
    $98–453

  3. Train

    1. Take the train from South Norwalk 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
    22h 40m
    $328–646

  4. Bus

    1. Take the bus from Bridgeport Bus Stop to Port Authority Bus Terminalbus bus Greyhound US0255s
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    23h 5m
    $142–241

  5. Drive 832.5 mi

    1. Drive from Wilton to Chicagocar car 832.5 mi
    14h 2m
    $152–220

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

    1. Take the train from South Norwalk to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    6h 36m
    $107–511

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

    1. Take the train from South Norwalk 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
    7h 1m
    $424–903

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

    1. Take the train from South Norwalk 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
    7h 35m
    $145–710

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

    1. Take the train from South Norwalk 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
    8h 15m
    $109–450

  10. Train, bus

    1. Take the train from South Norwalk to 125th Street - Harlemtrain train New Haven / ...
    2. Take the bus from New York City Chinatown to Chicago Bus Stationbus bus FlixBus N2640
    25h 34m
    $156–278

Wilton to Chicago by train

Calendar7Weekly Trains
Duration22h 40mAverage Duration
Ticket$328Cheapest Price
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Questions & Answers

Map of how to get from Wilton to Chicago.ExpandLaunch map view
  • Distance: 785.6 mi
  • Duration: 6h 15m

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

You can take a train from Wilton to Chicago Union Station via South Norwalk, 125th Street - Harlem, and Croton-Harmon Amtrak Station in around 22h 40m. Alternatively, you can take a bus from Wilton Center to Chicago Bus Station via Burnell Blvd. at Norwalk Wheel Hub, Bridgeport Bus Stop, Port Authority Bus Terminal, and New York Midtown in around 23h 5m.

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