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How to get fromChicago to Sag Harborby plane, train, bus, bus (Flixbus), train (Amtrak), car, car ferry or bus (Greyhound)

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There are 12 ways to get from Chicago to Sag Harbor by plane, train, bus, bus (Flixbus), train (Amtrak), car, car ferry, or bus (Greyhound)

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 Laguardia Airport, train, bus

    best
    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from Woodside to Ronkonkomatrain train
    3. Take the bus from Islip Airport Connection to Sag Harbor WBbus bus
    8h 4m
    $118–548

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

    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 New Londontrain train
    3. Take the car ferry from New London to Orient Pointcarferry car ferry
    4. Drive from Orient Point to Sag Harborcar car
    10h 39m
    $92–617

  3. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2640
    2. Take the bus from 40th & Lex to Sag Harbor-Eastboundbus bus To Sag Harbor-Eastbound / ...
    24h 12m
    $129–240

  4. Train

    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 New York Penn Station to East Hamptontrain train Montauk Branch
    24h 24m
    $147–371

  5. Drive 889 mi

    1. Drive from Chicago to Sag Harborcar car 889 mi
    15h 14m
    $163–235

  6. Fly Chicago O'Hare International Airport to John F. Kennedy International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK)plane plane ORD - JFK
    2. Take the train from Jamaica to East Hamptontrain train
    8h 51m
    $786–1,072

  7. Fly Chicago O'Hare International Airport to Newark Liberty International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane plane ORD - EWR
    2. Take the train from New York Penn Station to East Hamptontrain train
    8h 53m
    $98–376

  8. Fly Chicago O'Hare International Airport to Westchester County Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the bus from 40th & Lex to Sag Harbor-Eastboundbus bus
    10h 22m
    $130–568

  9. Fly Chicago Midway International Airport to Theodore Francis Green State Airport, train, car ferry, drive

    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 New Londontrain train
    3. Take the car ferry from New London to Orient Pointcarferry car ferry
    4. Drive from Orient Point to Sag Harborcar car
    10h 13m
    $112–727

  10. Fly Chicago Midway International Airport to Bradley International Airport, bus, drive

    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
    3. Drive from Old Saybrook RR Stn to Sag Harborcar car
    10h 10m
    $144–665

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

    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
    3. Drive from Old Saybrook RR Stn to Sag Harborcar car
    10h 40m
    $110–485

  12. Bus via Baltimore

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore Downtown Bus Station to Port Authority Bus Terminalbus bus
    3. Take the bus from 40th & Lex to Sag Harbor-Eastboundbus bus
    25h 29m
    $140–330

Chicago to Sag Harbor by bus and foot

Calendar7Weekly Services
Duration24h 12mAverage Duration
Ticket$129Cheapest Price
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Questions & Answers

What companies run services between Chicago, IL, USA and Sag Harbor, NY, USA?

You can take a bus from Chicago Bus Station to Sag Harbor-Eastbound via New York Midtown, W 34 St/7 Av, E 34 St/5 Av, and 40th & Lex in around 24h 12m. Alternatively, you can take a train from Chicago Union Station to NYS 114/Liberty St via Ny Moynihan Train Hall At Penn Station, New York Penn Station, East Hampton, and East Hampton LIRR in around 24h 24m.

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