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How to get fromChicago to Block Islandby plane, train, ferry, or bus

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There are 11 ways to get from Chicago to Block Island by plane, train, ferry, 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. Fly Chicago Midway International Airport to Boston Logan Airport, train, ferry

    best
    1. Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane plane MDW - BOS
    2. Take the train from Boston to New Londontrain train
    3. Take the ferry from New London to Block Islandferry ferry
    9h 23m
    $172–618

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

    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 ferry from New London to Block Islandferry ferry
    10h 4m
    $114–401

  3. Bus, ferry

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus
    2. Take the bus from 40th & Lex to Montaukbus bus
    3. Take the ferry from Montauk to Block Islandferry ferry
    23h 45m
    $231–381

  4. Train, ferry via New York

    1. Take the train from Chicago Union Station to Ny Moynihan Train Hall At Penn Stationtrain train
    2. Take the train from Ny Moynihan Train Hall At Penn Station to New Londontrain train
    3. Take the ferry from New London to Block Islandferry ferry
    26h 12m
    $386–740

  5. Fly Chicago O'Hare International Airport to Boston Logan Airport, train, ferry

    1. Fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS)plane plane ORD - BOS
    2. Take the train from Boston to New Londontrain train
    3. Take the ferry from New London to Block Islandferry ferry
    9h 43m
    $148–508

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

    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 ferry from New London to Block Islandferry ferry
    9h 34m
    $134–491

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

    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from Ny Moynihan Train Hall At Penn Station to New Londontrain train
    3. Take the ferry from New London to Block Islandferry ferry
    10h 24m
    $226–680

  8. Fly Chicago Midway International Airport to Bradley International Airport, train, ferry

    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    2. Take the train from Windsor Locks to New Haventrain train
    3. Take the train from New Haven to New Londontrain train
    4. Take the ferry from New London to Block Islandferry ferry
    10h 11m
    $158–588

  9. Fly Chicago O'Hare International Airport to Bradley International Airport, train, ferry

    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane plane ORD - BDL
    2. Take the train from Windsor Locks to New Haventrain train
    3. Take the train from New Haven to New Londontrain train
    4. Take the ferry from New London to Block Islandferry ferry
    10h 42m
    $132–478

  10. Train, ferry

    1. Take the train from Chicago Union Station to Bostontrain train
    2. Take the train from Boston to New Londontrain train
    3. Take the ferry from New London to Block Islandferry ferry
    26h 53m
    $395–762

  11. Bus, ferry 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 41st St bet 3rd & Lex to Orient Pointbus bus
    4. Take the ferry from Orient Point to Block Islandferry ferry
    29h 40m
    $226–471

Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS) flights

Calendar39Weekly Planes
Duration2h 27mAverage Duration
Ticket$102Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Block Island.ExpandLaunch map view
  • Distance: 1,024 mi
  • Duration: 9h 23m

What companies run services between Chicago, IL, USA and Block Island, RI, USA?

There is no direct connection from Chicago to Block Island. However, you can take the subway to Midway, walk to Chicago-Midway-Airport-MDW airport, fly to Boston Logan Airport (BOS), walk to Terminal C - Arrivals, LEX Pick Up, take the bus to Stuart St @ Dartmouth St, walk to Boston, take the train to New London, walk to New London, then take the ferry to Block Island. Alternatively, you can take a bus from Chicago Bus Station to Block Island via New York Midtown, W 34 St/7 Av, E 34 St/3 Av, 40th & Lex, Montauk, and Montauk in around 23h 45m.

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