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How to get fromChicago to Boothbay Harborby plane, bus, train, bus (Greyhound, Amtrak), car, or bus (Flixbus, Amtrak)

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There are 9 ways to get from Chicago to Boothbay Harbor by plane, bus, train, bus (Greyhound, Amtrak), car, or bus (Flixbus, Amtrak)

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 Portland, bus

    best
    1. Fly from Chicago Midway International Airport (MDW) to Portland (PWM)plane plane MDW - PWM
    2. Take the bus from Congress St + Maine Med to Bath Info Ctr + Biwbus bus
    7h 31m
    $202–758

  2. Fly Chicago O'Hare International Airport to Portland, bus

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Portland (PWM)plane plane ORD - PWM
    2. Take the bus from Congress St + Maine Med to Bath Info Ctr + Biwbus bus
    7h 56m
    $176–578

  3. Train, Amtrak Thruway

    1. Take the train from Chicago Union Station to Bostontrain train Lake Shore Limited
    2. Take the bus from South Station to Bath, MEbus bus Boston
    26h 29m
    $443–801

  4. Bus, Amtrak Thruway via Brook Park

    1. Take the bus from Chicago Bus Station to Cleveland Bus Stationbus bus
    2. Take the bus from Cleveland Bus Station to Bostonbus bus
    3. Take the bus from South Station to Bath, MEbus bus
    26h 32m
    $261–439

  5. Drive 1,091 mi

    1. Drive from Chicago to Boothbay Harborcar car 1,091 mi
    20h 31m
    $200–288

  6. Fly Chicago O'Hare International Airport to Bangor, Amtrak Thruway

    1. Fly from Chicago O'Hare International Airport (ORD) to Bangor (BGR)plane plane ORD - BGR
    2. Take the bus from Bangor, ME to Wiscassetbus bus
    9h 33m
    $184–717

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

    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 Bath, MEbus bus
    8h 42m
    $210–672

  8. Fly Chicago Midway International Airport to Manchester Airport, bus, Amtrak Thruway

    1. Fly from Chicago Midway International Airport (MDW) to Manchester Airport (MHT)plane plane MDW - MHT
    2. Take the bus from Boston Manchester Airport to Bostonbus bus
    3. Take the bus from South Station to Bath, MEbus bus
    10h 37m
    $238–760

  9. Bus, Amtrak Thruway

    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 South Station to Wiscassetbus bus
    26h 54m
    $245–389

Chicago Midway International Airport (MDW) to Portland (PWM) flights

Calendar19Weekly Planes
Duration3h 56mAverage Duration
Ticket$125Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Boothbay Harbor.ExpandLaunch map view
  • Distance: 969.1 mi
  • Duration: 7h 31m

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

You can take a bus from Chicago Bus Station to Boothbay Harbor via Cleveland Bus Station, Boston, South Station, and Bath, ME in around 26h 32m.

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