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How to get fromChicago to Shelter Islandby plane, unknown, bus, or train

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There are 10 ways to get from Chicago to Shelter Island by plane, unknown, bus, or train

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 O'Hare International Airport to Tweed-New Haven Airport, travel

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Tweed-New Haven Airport (HVN)plane plane ORD - HVN
    2. Walk from New-Haven-Airport-HVN to Shelter Islandunknown unknown
    5h 19m

  2. Bus, travel

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus
    2. Take the bus from 79th St & Broadway to Sag Harbor Westboundbus bus
    3. Walk from Sag Harbor Westbound to Shelter Islandunknown unknown
    20h 44m

  3. Train, travel via Springfield

    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
    4. Walk from Old Saybrook Amtrak Station to Shelter Islandunknown unknown
    23h 21m

  4. Fly Chicago Midway International Airport to Bradley International Airport, bus, travel

    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. Walk from Old Saybrook RR Stn to Shelter Islandunknown unknown
    6h 55m

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

    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. Walk from Old Saybrook RR Stn to Shelter Islandunknown unknown
    7h 25m

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

    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 Ronkonkomatrain train
    3. Take the train from Ronkonkoma to Greenporttrain train
    4. Walk from Greenport to Shelter Islandunknown unknown
    7h 54m

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

    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 train from Ronkonkoma to Greenporttrain train
    4. Walk from Greenport to Shelter Islandunknown unknown
    8h 4m

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

    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
    3. Walk from Old Saybrook Amtrak Station to Shelter Islandunknown unknown
    7h 48m

  9. Train, travel

    1. Take the train from Chicago Union Station to Ny Moynihan Train Hall At Penn Stationtrain train
    2. Take the train from New York Penn Station to Ronkonkomatrain train
    3. Take the train from Ronkonkoma to Greenporttrain train
    4. Walk from Greenport to Shelter Islandunknown unknown
    24h 15m

  10. Bus, travel 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 Boerum Hill-Atlantic & 4 Av to Greenportbus bus
    4. Walk from Greenport to Shelter Islandunknown unknown
    26h 23m

Chicago O'Hare International Airport (ORD) to Tweed-New Haven Airport (HVN) flights

Calendar4Weekly Planes
Duration2h 32mAverage Duration
Ticket$142Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Shelter Island.ExpandLaunch map view
  • Distance: 825.8 mi
  • Duration: 5h 19m

What companies run services between Chicago, IL, USA and Shelter Island, NY, USA?

There is no direct connection from Chicago to Shelter Island. However, you can take the subway to O'Hare, walk to Chicago O'Hare International Airport (ORD) airport, fly to Tweed-New Haven Airport (HVN), then travel to Shelter Island. Alternatively, you can take a bus from Chicago Bus Station to Shelter Island via New York Midtown, 34 St-Penn Station, 79 St, 79th St & Broadway, and Sag Harbor Westbound in around 20h 44m.

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