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How to get fromOld Saybrook to Chicagoby train, plane, bus (Flixbus), train (Amtrak), car, or bus

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There are 11 ways to get from Old Saybrook to Chicago by train, plane, bus (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, train to Laguardia Airport, fly to Chicago Midway International Airport

    best
    1. Take the train from Old Saybrook Amtrak Station to Stamford Amtrak Stationtrain train
    2. Take the train from Stamford to 125th Street - Harlemtrain train
    3. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    6h 55m
    $237–626

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

    cheapest
    1. Take the train from Old Saybrook Amtrak 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
    7h 43m
    $88–401

  3. Bus

    1. Take the bus from Old Saybrook Trans Cntr to Asylum St @ Union Plbus bus 921
    2. Take the bus from Hartford Union Station to Port Authority Bus Terminalbus bus
    3. Take the bus from New York Midtown to Chicago Bus Stationbus bus
    22h 48m
    $156–286

  4. Train via New York (Amtrak)

    1. Take the train from Old Saybrook Amtrak 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 / ...
    22h 49m
    $323–719

  5. Drive 887.8 mi

    1. Drive from Old Saybrook to Chicagocar car 887.8 mi
    15h 5m
    $162–234

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

    1. Take the train from Old Saybrook Amtrak Station to Providencetrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    6h 55m
    $102–453

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

    1. Take the train from Old Saybrook Amtrak 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 9m
    $103–471

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

    1. Take the train from Old Saybrook Amtrak Station to New Haventrain train
    2. Fly from Tweed-New Haven Airport (HVN) to Chicago O'Hare International Airport (ORD)plane plane HVN - ORD
    6h 3m
    $179–496

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

    1. Take the train from Old Saybrook Amtrak Station to Providencetrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane plane PVD - ORD
    7h 26m
    $92–393

  10. Train

    1. Take the train from Old Saybrook Amtrak Station to New Haventrain train
    2. Take the train from New Haven to Springfieldtrain train
    3. Take the train from Springfield to Chicago Union Stationtrain train
    23h 54m
    $294–648

  11. Train, bus

    1. Take the train from Old Saybrook Amtrak Station 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
    27h 3m
    $172–378

Old Saybrook to Chicago by bus and foot

Calendar15Weekly Services
Duration22h 48mAverage Duration
Ticket$156Cheapest Price
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Questions & Answers

Map of how to get from Old Saybrook to Chicago.ExpandLaunch map view
  • Distance: 842.1 mi
  • Duration: 6h 55m

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

You can take a bus from Old Saybrook Trans Cntr to Chicago Bus Station via Asylum St @ Union Pl, Hartford Union Station, Port Authority Bus Terminal, and New York Midtown in around 22h 48m. Alternatively, you can take a train from Old Saybrook Amtrak Station to Chicago Union Station via Ny Moynihan Train Hall At Penn Station in around 22h 49m.

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