Rome2Rio

How to get fromChicago to Portland, MEby plane, train, bus, bus (Flixbus, Amtrak) or car

Find Transport to Portland, ME

See all options

There are 7 ways to get from Chicago to Portland, ME by plane, train, bus, bus (Flixbus, Amtrak), 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 Portland

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Portland (PWM)plane plane ORD - PWM
    4h 54m
    $82–425

  2. Train, bus

    1. Take the train from Chicago Union Station to Bostontrain train Lake Shore Limited
    2. Take the bus from Boston, MA - South Station to Portland, MEbus bus Logan Airport / ...
    24h 16m
    $111–402

  3. Bus

    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 Boston, MA - South Station to Portland, MEbus bus
    27h 41m
    $148–353

  4. Drive 1,034.9 mi

    1. Drive from Chicago to Portland, MEcar car 1,034.9 mi
    19h 12m
    $189–273

  5. Fly Chicago Midway International Airport to Portland

    1. Fly from Chicago Midway International Airport (MDW) to Portland (PWM)plane plane MDW - PWM
    4h 31m
    $112–605

  6. Fly Chicago O'Hare International Airport to Boston Logan Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS)plane plane ORD - BOS
    2. Take the bus from Logan International Airport to Portland, MEbus bus
    6h 53m
    $134–435

  7. Fly Chicago Midway International Airport to Boston Logan Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane plane MDW - BOS
    2. Take the bus from Logan International Airport to Portland, MEbus bus
    6h 29m
    $134–635

Chicago to Portland, ME by train and bus

Calendar7Weekly Services
Duration24h 16mAverage Duration
Ticket$111Cheapest Price
See schedules

Questions & Answers

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

American Airlines, United Airlines, and Delta fly from Chicago O'Hare International Airport (ORD) to Portland (PWM) every 4 hours. Alternatively, you can take a bus from Chicago Bus Station to Portland, ME via New York Midtown, Boston, and Boston, MA - South Station in around 27h 41m.

Airlines
Train operators
Bus 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

More Questions & Answers

Trips from Chicago

Trips to Portland, ME

Popular routes