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How to get fromBoothbay to Chicagoby taxi, train, plane, bus, bus (Amtrak, Flixbus) or car

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There are 9 ways to get from Boothbay to Chicago by taxi, train, plane, bus, bus (Amtrak, Flixbus), 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. Taxi, train to Portland, fly to Chicago Midway International Airport

    best
    1. Take the taxi from Boothbay to Brunswick Amtrak Stationtaxi
    2. Take the train from Brunswick Amtrak Station to Portlandtrain
    3. Fly from Portland (PWM) to Chicago Midway International Airport (MDW)planePWM - MDW
    7h 6m
    $207–683
  2. Amtrak Thruway to Bangor, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the bus from Wiscasset to Bangor, MEbus
    2. Fly from Bangor (BGR) to Chicago O'Hare International Airport (ORD)planeBGR - ORD
    8h 41m
    $141–457
  3. Amtrak Thruway, train

    1. Take the bus from Wiscasset to South StationbusBangor
    2. Take the train from Boston to Chicago Union StationtrainLake Shore Limited
    27h 18m
    $215–850
  4. Amtrak Thruway, bus

    1. Take the bus from Wiscasset to South Stationbus
    2. Take the bus from Boston to New York Midtownbus
    3. Take the bus from New York Midtown to Chicago Bus Stationbus
    30h 43m
    $200–380
  5. Drive 1,091.2 mi

    1. Drive from Boothbay to Chicagocar1,091.2 mi
    20h 14m
    $200–288
  6. Taxi, train to Portland, fly to Chicago O'Hare International Airport

    1. Take the taxi from Boothbay to Brunswick Amtrak Stationtaxi
    2. Take the train from Brunswick Amtrak Station to Portlandtrain
    3. Fly from Portland (PWM) to Chicago O'Hare International Airport (ORD)planePWM - ORD
    7h 51m
    $182–533
  7. Taxi, train, bus to Boston Logan Airport, fly to Chicago Midway International Airport

    1. Take the taxi from Boothbay to Brunswick Amtrak Stationtaxi
    2. Take the train from Brunswick Amtrak Station to Portlandtrain
    3. Take the bus from Portland, ME to Logan International Airportbus
    4. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)planeBOS - MDW
    8h 25m
    $212–599
  8. Amtrak Thruway, bus to Manchester Airport, fly to Chicago Midway International Airport

    1. Take the bus from Bath, ME to South Stationbus
    2. Take the bus from Boston to Boston Manchester Airportbus
    3. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)planeMHT - MDW
    10h 6m
    $217–716
  9. Amtrak Thruway, bus to Manchester Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Bath, ME to South Stationbus
    2. Take the bus from Boston to Boston Manchester Airportbus
    3. Fly from Manchester Airport (MHT) to Chicago O'Hare International Airport (ORD)planeMHT - ORD
    10h 32m
    $192–576

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

Calendar24Weekly Planes
Duration5h 12mAverage Duration
Ticket$104Cheapest Price
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Questions & Answers

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

You can take a vehicle from Boothbay to Chicago Bus Station via Wiscasset, South Station, Boston, and New York Midtown in around 30h 43m.

Airlines
Train operators
Bus operators
Other operators

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