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

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There are 12 ways to get from Old Saybrook to Chicago by train, plane, train (Amtrak), bus (Flixbus), 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 New Haventrain train
    2. Take the train from New Haven to 125th Street - Harlemtrain train
    3. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    7h 48m
    $106–694

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

    cheapest
    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 27m
    $60–492

  3. 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 41m
    $135–664

  4. 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 Times Square – 37th St.bus bus
    3. Take the bus from New York Midtown to Chicago Bus Stationbus bus
    25h 30m
    $102–256

  5. Drive 887.8 mi

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

  6. 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 22m
    $104–904

  7. 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
    7h 5m
    $80–602

  8. Train, train to Bradley International Airport, fly to Chicago O'Hare 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 O'Hare International Airport (ORD)plane plane BDL - ORD
    7h 43m
    $74–754

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

    1. Take the train from Old Saybrook Amtrak Station to Stamford Amtrak Stationtrain train
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    8h 21m
    $71–558

  10. Train, train to Laguardia Airport, fly to General Mitchell International Airport

    1. Take the train from Old Saybrook Amtrak Station to New Haventrain train
    2. Take the train from New Haven to 125th Street - Harlemtrain train
    3. Fly from Laguardia Airport (LGA) to General Mitchell International Airport (MKE)plane plane LGA - MKE
    4. Take the train from Milwaukee to Chicago Union Stationtrain train
    10h 19m
    $238–899

  11. 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 55m
    $143–866

  12. 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 1m
    $120–481

Old Saybrook to Chicago by train (Amtrak)

Calendar10Weekly Trains
Duration22h 41mAverage Duration
Ticket$135Cheapest Price
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Questions & Answers

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

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 41m. Alternatively, you can take a bus from Old Saybrook Trans Cntr to Chicago Bus Station via Asylum St @ Union Pl, Hartford Union Station, Times Square – 37th St., and New York Midtown in around 25h 30m.

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