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

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There are 11 ways to get from Shelton to Chicago by train, plane, bus (Greyhound, Flixbus), train (Amtrak), 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 Bridgeport to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    6h 42m
    $227–598

  2. Train to Bradley International Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the train from New Haven to Windsor Lockstrain train
    2. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    7h 41m
    $85–386

  3. Bus

    1. Take the bus from New Haven Union Station to Port Authority Bus Terminalbus bus Providence
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    21h 51m
    $154–286

  4. Train

    1. Take the train from Bridgeport 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
    23h 8m
    $322–702

  5. Drive 850.8 mi

    1. Drive from Shelton to Chicagocar car 850.8 mi
    14h 23m
    $156–225

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

    1. Take the train from Bridgeport to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    7h 3m
    $237–698

  7. Train to Bradley International Airport, fly to Chicago Midway International Airport

    1. Take the train from New Haven to Windsor Lockstrain train
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    7h 7m
    $95–446

  8. Fly Tweed-New Haven Airport to Chicago O'Hare International Airport

    1. Fly from Tweed-New Haven Airport (HVN) to Chicago O'Hare International Airport (ORD)plane plane HVN - ORD
    6h 14m
    $175–491

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

    1. Take the train from Derby-Shelton to Bridgeporttrain train
    2. Take the train from Bridgeport 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
    8h 12m
    $110–509

  10. Train via Springfield (Amtrak)

    1. Take the train from New Haven to Springfieldtrain train Amtrak Hartford Line / ...
    2. Take the train from Springfield to Chicago Union Stationtrain train Lake Shore Limited
    23h 52m
    $311–698

  11. Train, bus

    1. Take the train from Bridgeport 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
    26h 36m
    $175–384

Shelton to Chicago by bus and foot

Calendar15Weekly Services
Duration21h 51mAverage Duration
Ticket$154Cheapest Price
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Questions & Answers

Map of how to get from Shelton to Chicago.ExpandLaunch map view
  • Distance: 806.4 mi
  • Duration: 6h 42m

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

You can take a bus from Howe Ave @ Cornell St to Chicago Bus Station via Elm St @ Church St, Temple St @ Chapel St, New Haven Union Station, Port Authority Bus Terminal, and New York Midtown in around 21h 51m. Alternatively, you can take a train from Derby-Shelton to Chicago Union Station via Bridgeport, 125th Street - Harlem, and Croton-Harmon Amtrak Station in around 23h 8m.

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