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

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There are 10 ways to get from Stratford 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 Stratford to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    6h 10m
    $221–587

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

    cheapest
    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
    6h 57m
    $100–455

  3. 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 / ...
    21h 38m
    $150–269

  4. Train

    1. Take the train from Stratford 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 36m
    $326–691

  5. Drive 843.1 mi

    1. Drive from Stratford to Chicagocar car 843.1 mi
    14h 14m
    $154–223

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

    1. Take the train from Stratford to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    6h 31m
    $231–687

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

    1. Take the train from Stratford 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 54m
    $343–898

  8. Train to Westchester County Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Stratford to Stamfordtrain train
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    7h 45m
    $106–497

  9. 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 34m
    $182–509

  10. Train, bus

    1. Take the train from Stratford 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 32m
    $175–383

Stratford to Chicago by bus and foot

Calendar7Weekly Services
Duration21h 38mAverage Duration
Ticket$150Cheapest Price
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Questions & Answers

Map of how to get from Stratford to Chicago.ExpandLaunch map view
  • Distance: 795.9 mi
  • Duration: 6h 10m

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

You can take a bus from Stratford Ave. at Beardsley Ave. to Chicago Bus Station via Bridgeport Bus Stop, Port Authority Bus Terminal, and New York Midtown in around 21h 38m. Alternatively, you can take a train from Stratford to Chicago Union Station via 125th Street - Harlem and Croton-Harmon Amtrak Station in around 22h 36m.

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