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How to get fromChicago to Old Saybrookby plane, bus, train (Amtrak), train, car, or bus (Flixbus)

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There are 12 ways to get from Chicago to Old Saybrook by plane, bus, train (Amtrak), train, car, or bus (Flixbus)

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Fly Chicago Midway International Airport to Bradley International Airport, bus

    best
    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    2. Take the bus from Central Row South Side @ Travelers to Old Saybrook RR Stnbus bus
    6h 24m
    $146–809

  2. Fly Chicago O'Hare International Airport to Theodore Francis Green State Airport, train

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Theodore Francis Green State Airport (PVD)plane plane ORD - PVD
    2. Take the train from Providence to Old Saybrook Amtrak Stationtrain train
    7h 40m
    $94–342

  3. Train

    1. Take the train from Chicago Union Station to Springfieldtrain train
    2. Take the train from Springfield to New Haventrain train
    3. Take the train from New Haven to Old Saybrook Amtrak Stationtrain train
    22h 50m
    $541–838

  4. Bus, train

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore to New Yorkbus bus
    3. Take the train from Grand Central Terminal to New Haventrain train
    4. Take the train from New Haven to Old Saybrook Amtrak Stationtrain train
    26h 9m
    $210–332

  5. Drive  887.3 mi

    1. Drive from Chicago to Old Saybrookcar car 887.3 mi
    15h 7m
    $162–234

  6. Fly Chicago O'Hare International Airport to Bradley International Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane plane ORD - BDL
    2. Take the bus from Central Row South Side @ Travelers to Old Saybrook RR Stnbus bus
    6h 49m
    $102–509

  7. Fly Chicago Midway International Airport to Laguardia Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from 125th Street - Harlem to New Haventrain train
    3. Take the train from New Haven to Old Saybrook Amtrak Stationtrain train
    7h 46m
    $230–699

  8. Fly Chicago Midway International Airport to Theodore Francis Green State Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Theodore Francis Green State Airport (PVD)plane plane MDW - PVD
    2. Take the train from Providence to Old Saybrook Amtrak Stationtrain train
    7h 12m
    $118–482

  9. Fly Chicago O'Hare International Airport to Westchester County Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the train from Stamford Amtrak Station to Old Saybrook Amtrak Stationtrain train
    8h 56m
    $122–525

  10. Fly Chicago O'Hare International Airport to Tweed-New Haven Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Tweed-New Haven Airport (HVN)plane plane ORD - HVN
    2. Take the train from New Haven to Old Saybrook Amtrak Stationtrain train
    7h 30m
    $142–507

  11. Train via New York (Amtrak)

    1. Take the train from Chicago Union Station to Ny Moynihan Train Hall At Penn Stationtrain train Lake Shore Limited / ...
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Old Saybrook Amtrak Stationtrain train Northeast Regional
    23h 22m
    $582–904

  12. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus
    2. Take the bus from New York to Hartfordbus bus
    3. Take the bus from Asylum St @ Bushnell Park to Old Saybrook RR Stnbus bus 921
    26h 11m
    $184–281

Chicago to Old Saybrook by train

Calendar7Weekly Trains
Duration22h 50mAverage Duration
Ticket$541Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Old Saybrook.ExpandLaunch map view
  • Distance: 840.7 mi
  • Duration: 6h 24m

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

You can take a train from Chicago Union Station to Old Saybrook Amtrak Station via Springfield and New Haven in around 22h 50m. Alternatively, you can take a bus from Chicago Bus Station to Old Saybrook RR Stn via New York Midtown, 8 Av/W 31 St, 8 Av/W 41 St, New York, Hartford, and Asylum St @ Bushnell Park in around 26h 11m.

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