Rome2Rio

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

Find Transport to Chicago

See all options

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

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Bus to Portland, fly to Chicago O'Hare International Airport

    best
    1. Take the bus from Bath Info Ctr + Biw to Congress St + Forest St/Mmcbus bus
    2. Fly from Portland (PWM) to Chicago O'Hare International Airport (ORD)plane plane PWM - ORD
    7h 37m
    $187–697

  2. Amtrak Thruway to Bangor, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the bus from Wiscasset to Bangor, MEbus bus
    2. Fly from Bangor (BGR) to Chicago O'Hare International Airport (ORD)plane plane BGR - ORD
    9h 2m
    $161–557

  3. Amtrak Thruway, bus

    1. Take the bus from Wiscasset to South Stationbus bus
    2. Take the bus from Boston to New York Midtownbus bus
    3. Take the bus from New York Midtown to Chicago Bus Stationbus bus
    27h 2m
    $212–350

  4. Amtrak Thruway, train

    1. Take the bus from Wiscasset to South Stationbus bus Bangor
    2. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    27h 18m
    $345–700

  5. Drive 1,090.5 mi

    1. Drive from Boothbay to Chicagocar car 1,090.5 mi
    20h 26m
    $199–288

  6. Bus to Portland, fly to Chicago Midway International Airport

    1. Take the bus from Bath Info Ctr + Biw to Congress St + Forest St/Mmcbus bus
    2. Fly from Portland (PWM) to Chicago Midway International Airport (MDW)plane plane PWM - MDW
    7h 10m
    $227–897

  7. Taxi, train, bus to Boston Logan Airport, fly to Chicago Midway International Airport

    1. Take the taxi from Boothbay to Brunswick Amtrak Stationtaxi taxi
    2. Take the train from Brunswick Amtrak Station to Portlandtrain train
    3. Take the bus from Portland, ME to Logan International Airportbus bus
    4. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    8h 20m
    $219–628

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

    1. Take the bus from Bath, ME to South Stationbus bus
    2. Take the bus from Boston to Boston Manchester Airportbus bus
    3. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)plane plane MHT - MDW
    10h 6m
    $222–754

  9. Amtrak Thruway, bus via Brook Park

    1. Take the bus from Wiscasset to South Stationbus bus
    2. Take the bus from Boston to Cleveland Bus Stationbus bus
    3. Take the bus from Cleveland Bus Station to Chicago Bus Stationbus bus
    27h 26m
    $240–430

Portland (PWM) to Chicago O'Hare International Airport (ORD) flights

Calendar75Weekly Planes
Duration4h 23mAverage Duration
Ticket$111Cheapest Price
See schedules

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 27h 2m.

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

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

Where to next?

Trips from Boothbay

Trips to Chicago

Popular routes