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How to get fromChicago to Deer Isleby plane, bus, train, car, or taxi

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There are 9 ways to get from Chicago to Deer Isle by plane, bus, train, car, or taxi

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 Bangor, bus

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Bangor (BGR)plane plane ORD - BGR
    2. Take the bus from Bangor International Airport to Ellsworth City Hallbus bus
    3. Take the bus from Ellsworth City Hall to Deer Isle - Deer Run Apartmentsbus bus
    8h 24m
    $74–475

  2. Train, Amtrak Thruway, drive (Amtrak)

    1. Take the train from Chicago Union Station to Bostontrain train
    2. Take the bus from South Station to Lincolnville, MEbus bus
    3. Drive from Lincolnville, ME to Deer Islecar car
    29h 21m
    $603–922

  3. Bus, drive

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus
    2. Take the bus from New York Midtown to Bostonbus bus
    3. Take the bus from Boston South Buses to Lincolnville, MEbus bus
    4. Drive from Lincolnville, ME to Deer Islecar car
    32h 16m
    $243–358

  4. Drive  1,161.5 mi

    1. Drive from Chicago to Deer Islecar car 1,161.5 mi
    21h 32m
    $199–287

  5. Fly Chicago O'Hare International Airport to Portland, Amtrak Thruway, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to Portland (PWM)plane plane ORD - PWM
    2. Take the bus from Portland, ME to Lincolnville, MEbus bus
    3. Drive from Lincolnville, ME to Deer Islecar car
    10h 55m
    $100–424

  6. Fly Chicago Midway International Airport to Hancock County-Bar Harbor Airport, taxi

    1. Fly from Chicago Midway International Airport (MDW) to Hancock County-Bar Harbor Airport (BHB)plane plane MDW - BHB
    2. Take the taxi from Hancock County-Bar Harbor Airport (BHB) to Deer Isletaxi taxi
    7h 15m
    $248–875

  7. Fly Chicago Midway International Airport to Portland, Amtrak Thruway, drive

    1. Fly from Chicago Midway International Airport (MDW) to Portland (PWM)plane plane MDW - PWM
    2. Take the bus from Portland, ME to Lincolnville, MEbus bus
    3. Drive from Lincolnville, ME to Deer Islecar car
    10h 33m
    $146–674

  8. Fly Chicago Midway International Airport to Rockland, drive

    1. Fly from Chicago Midway International Airport (MDW) to Rockland (RKD)plane plane MDW - RKD
    2. Drive from Rockland (RKD) to Deer Islecar car
    9h 11m
    $106–485

  9. Train, bus

    1. Take the train from Chicago Union Station to Bostontrain train
    2. Take the bus from Boston, MA - South Station to Bangor Transportation Centerbus bus
    3. Take the bus from Bangor - Concord Coach to Ellsworth City Hallbus bus
    4. Take the bus from Ellsworth City Hall to Deer Isle - Deer Run Apartmentsbus bus
    31h 16m
    $600–1,036

Chicago O'Hare International Airport (ORD) to Bangor (BGR) flights

Calendar62Weekly Planes
Duration4h 58mAverage Duration
Ticket$72Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Deer Isle.ExpandLaunch map view
  • Distance: 1,064.8 mi
  • Duration: 8h 24m

What companies run services between Chicago, IL, USA and Deer Isle, ME, USA?

There is no direct connection from Chicago to Deer Isle. However, you can take the subway to O'Hare, walk to Chicago O'Hare International Airport (ORD) airport, fly to Bangor (BGR), walk to Bangor International Airport, take the bus to Ellsworth City Hall, then take the bus to Deer Isle - Deer Run Apartments. Alternatively, you can take a train from Chicago Union Station to Deer Isle via Boston, South Station, and Lincolnville, ME in around 29h 21m.

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