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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 11 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 O'Hare International Airport

    best
    1. Take the train from South Norwalk to 125th Street - Harlemtrain
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)planeLGA - ORD
    6h 32m
    $73–302

  2. Train

    1. Take the train from South Norwalk to 125th Street - Harlemtrain
    2. Take the train from 125th Street - Harlem to Croton-Harmontrain
    3. Take the train from Croton-Harmon Amtrak Station to Chicago Union Stationtrain
    22h 37m
    $159–417

  3. Bus

    1. Take the bus from Bridgeport Bus Stop to Port Authority Bus TerminalbusGreyhound US0255s
    2. Take the bus from New York Midtown to Chicago Bus StationbusFlixBus N2640
    26h 37m
    $111–294

  4. Drive 832.5 mi

    1. Drive from Wilton to Chicagocar832.5 mi
    13h 52m
    $152–220

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

    1. Take the train from South Norwalk to 125th Street - Harlemtrain
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)planeLGA - MDW
    6h 22m
    $98–472

  6. 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
    2. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)planeJFK - ORD
    7h 7m
    $834–1,054

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

    1. Take the train from Wilton to South Norwalktrain
    2. Take the train from South Norwalk to Stamfordtrain
    3. Take the bus from Stamford Transportation Center @ Bay A to South Broadway @ Main Stbus
    4. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)planeHPN - ORD
    7h 57m
    $85–395

  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
    2. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)planeEWR - ORD
    8h 16m
    $77–1,058

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

    1. Take the train from South Norwalk to New Haventrain
    2. Take the train from New Haven to Windsor Lockstrain
    3. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)planeBDL - MDW
    8h 27m
    $117–726

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

    1. Take the train from South Norwalk to 125th Street - Harlemtrain
    2. Fly from Laguardia Airport (LGA) to General Mitchell International Airport (MKE)planeLGA - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain
    8h 54m
    $215–637

  11. Train, bus

    1. Take the train from South Norwalk to Grand Central Terminaltrain
    2. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus
    3. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus
    26h 48m
    $132–349

Wilton to Chicago by train

Calendar7Weekly Trains
Duration22h 37mAverage Duration
Ticket$159Cheapest Price
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Questions & Answers

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 37m. 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 26h 37m.

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