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How to get fromStonington to Chicagoby train, plane, train (Amtrak), car ferry, car, or bus

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There are 11 ways to get from Stonington to Chicago by train, plane, train (Amtrak), car ferry, 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 Boston Logan Airport, fly to Chicago Midway International Airport

    best
    1. Take the train from Mystic Station to Bostontrain train
    2. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    6h 27m
    $128–514

  2. Train to Theodore Francis Green State Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the train from Mystic Station to Providencetrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane plane PVD - ORD
    6h 59m
    $99–384

  3. Train via New York (Amtrak)

    1. Take the train from Mystic Station to Ny Moynihan Train Hall At Penn Stationtrain train Northeast Regional
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    23h 42m
    $364–757

  4. Car ferry, drive, bus

    1. Take the car ferry from New London to Orient Pointcarferry car ferry
    2. Drive from Orient Point to Montauk Villagecar car
    3. Take the bus from Montauk Village to Hudson Yardsbus bus
    4. Take the bus from New York Midtown to Chicago Bus Stationbus bus
    25h 51m
    $199–413

  5. Drive 916.5 mi

    1. Drive from Stonington to Chicagocar car 916.5 mi
    15h 40m
    $168–242

  6. Train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport

    1. Take the train from Mystic Station to Providencetrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    6h 28m
    $109–444

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

    1. Take the train from Mystic Station 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 43m
    $126–480

  8. Train to Tweed-New Haven Airport, fly to Chicago O'Hare International Airport

    1. Take the train from New London to New Haventrain train
    2. Fly from Tweed-New Haven Airport (HVN) to Chicago O'Hare International Airport (ORD)plane plane HVN - ORD
    6h 54m
    $153–398

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

    1. Take the train from Mystic Station to New Haventrain train
    2. Take the train from New Haven to Windsor Lockstrain train
    3. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    8h 17m
    $116–420

  10. Train (Amtrak)

    1. Take the train from Mystic Station to Bostontrain train Northeast Regional
    2. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    24h 52m
    $374–782

  11. Train, bus

    1. Take the train from New London to New Haventrain train
    2. Take the bus from New Haven Union Station to Port Authority Bus Terminalbus bus
    3. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus bus
    4. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus
    28h 27m
    $202–435

Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW) flights

Calendar46Weekly Planes
Duration2h 49mAverage Duration
Ticket$83Cheapest Price
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Questions & Answers

Map of how to get from Stonington to Chicago.ExpandLaunch map view
  • Distance: 974.9 mi
  • Duration: 6h 27m

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

You can take a vehicle from Stonington to Chicago Union Station via Mystic Station and Ny Moynihan Train Hall At Penn Station in around 23h 42m.

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Bus operators
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