Rome2Rio

How to get fromChicago to Castineby plane, bus, taxi, train or car

Find Transport to Castine

See all options

There are 10 ways to get from Chicago to Castine by plane, bus, taxi, train, or car

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, Amtrak Thruway, taxi

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Bangor (BGR)planeORD - BGR
    2. Take the bus from Bangor, ME to Searsport, MEbus
    3. Take the taxi from Searsport, ME to Castinetaxi
    7h 32m
    $170–607

  2. Fly Chicago Midway International Airport to Rockland, drive

    cheapest
    1. Fly from Chicago Midway International Airport (MDW) to Rockland (RKD)planeMDW - RKD
    2. Drive from Rockland (RKD) to Castinecar
    7h 36m
    $134–672

  3. Train, Amtrak Thruway, taxi

    1. Take the train from Chicago Union Station to Bostontrain
    2. Take the bus from South Station to Searsport, MEbus
    3. Take the taxi from Searsport, ME to Castinetaxi
    28h 56m
    $238–808

  4. Bus, Amtrak Thruway, taxi

    1. Take the bus from Chicago Bus Station to New York Midtownbus
    2. Take the bus from New York Midtown to Bostonbus
    3. Take the bus from South Station to Searsport, MEbus
    4. Take the taxi from Searsport, ME to Castinetaxi
    32h 24m
    $243–470

  5. Drive 1,149.2 mi

    1. Drive from Chicago to Castinecar1,149.2 mi
    21h 17m
    $210–303

  6. Fly Chicago Midway International Airport to Bangor, Amtrak Thruway, taxi

    1. Fly from Chicago Midway International Airport (MDW) to Bangor (BGR)planeMDW - BGR
    2. Take the bus from Bangor, ME to Searsport, MEbus
    3. Take the taxi from Searsport, ME to Castinetaxi
    9h 12m
    $186–737

  7. Fly Chicago O'Hare International Airport to Portland, Amtrak Thruway, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Portland (PWM)planeORD - PWM
    2. Take the bus from Portland, ME to Searsport, MEbus
    3. Take the taxi from Searsport, ME to Castinetaxi
    10h 34m
    $184–603

  8. Fly Chicago Midway International Airport to Portland, Amtrak Thruway, taxi

    1. Fly from Chicago Midway International Airport (MDW) to Portland (PWM)planeMDW - PWM
    2. Take the bus from Portland, ME to Searsport, MEbus
    3. Take the taxi from Searsport, ME to Castinetaxi
    10h 16m
    $194–693

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

    1. Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)planeMDW - BOS
    2. Take the bus from South Station to Searsport, MEbus
    3. Take the taxi from Searsport, ME to Castinetaxi
    11h 2m
    $198–642

  10. 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)planeMDW - BHB
    2. Take the taxi from Hancock County-Bar Harbor Airport (BHB) to Castinetaxi
    7h 34m
    $218–725

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

Calendar69Weekly Planes
Duration4h 53mAverage Duration
Ticket$95Cheapest Price
See schedules

Questions & Answers

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

There is no direct connection from Chicago to Castine. 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 Airport, take the bus to Airport Mall, walk to Bangor, ME, take the bus to Searsport, ME, then take the taxi to Castine. Alternatively, you can take the train to Boston, walk to South Station, take the bus to Searsport, ME, then take the taxi to Castine.

Transport is disrupted due to the Russia-Ukraine war. Read more

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 Castine

Popular routes