Rome2Rio

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

Find Transport to Deer Isle

See all options

There are 10 ways to get from Chicago to Deer Isle by plane, car, train, bus, 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 Rockland, drive

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Rockland (RKD)plane plane ORD - RKD
    2. Drive from Rockland (RKD) to Deer Islecar car
    9h 10m
    $82–357

  2. Train, Amtrak Thruway, drive

    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 23m
    $332–696

  3. Bus, Amtrak Thruway, drive

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus
    2. Take the bus from New York Midtown to City of Portlandbus bus
    3. Take the bus from Congress St + Maine Med to Brunswick Train Stationbus bus Brz
    4. Take the bus from Brunswick, ME to Lincolnville, MEbus bus
    5. Drive from Lincolnville, ME to Deer Islecar car
    35h 14m
    $198–362

  4. Drive 1,167.6 mi

    1. Drive from Chicago to Deer Islecar car 1,167.6 mi
    21h 43m
    $214–308

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

    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 26m
    $92–595

  6. 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 32m
    $146–675

  7. 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 57m
    $116–505

  8. 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 17m
    $192–615

  9. Fly Chicago Midway International Airport to Boston Logan Airport, Amtrak Thruway, drive

    1. Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane plane MDW - BOS
    2. Take the bus from South Station to Lincolnville, MEbus bus
    3. Drive from Lincolnville, ME to Deer Islecar car
    11h 33m
    $150–709

  10. 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 17m
    $326–799

Chicago O'Hare International Airport (ORD) to Rockland (RKD) flights

Calendar38Weekly Planes
Duration8h 33mAverage Duration
Ticket$64Cheapest Price
See schedules

Questions & Answers

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 Rockland (RKD), then drive to Deer Isle. Alternatively, you can take a train from Chicago Union Station to Deer Isle via Boston, South Station, and Lincolnville, ME in around 29h 23m.

Airlines
Train operators
Bus operators
Other operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Trips from Chicago

Trips to Deer Isle

Popular routes