Rome2Rio

How to get fromChicago to Ossipeeby plane, taxi, train, bus (Flixbus), car or bus

Find Transport to Ossipee

See all options

There are 7 ways to get from Chicago to Ossipee by plane, taxi, train, bus (Flixbus), car, or bus

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, taxi

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Portland (PWM)plane plane ORD - PWM
    2. Take the taxi from Portland-Airport-PWM to Ossipeetaxi taxi
    5h 32m
    $242–625

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

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Manchester Airport (MHT)plane plane ORD - MHT
    2. Take the bus from Concord, NH to West Ossipeebus bus
    8h 47m
    $144–539

  3. Train, taxi

    1. Take the train from Chicago Union Station to Bostontrain train
    2. Take the train from Boston to Dovertrain train
    3. Take the taxi from Dover to Ossipeetaxi taxi
    25h 27m
    $369–907

  4. 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 - South Station to West Ossipeebus bus
    29h 43m
    $190–398

  5. Drive 1,000.8 mi

    1. Drive from Chicago to Ossipeecar car 1,000.8 mi
    18h 24m
    $183–264

  6. Fly Chicago Midway International Airport to Portland, taxi

    1. Fly from Chicago Midway International Airport (MDW) to Portland (PWM)plane plane MDW - PWM
    2. Take the taxi from Portland-Airport-PWM to Ossipeetaxi taxi
    5h 8m
    $272–805

  7. Fly Chicago Midway International Airport to Manchester Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Manchester Airport (MHT)plane plane MDW - MHT
    2. Take the bus from Concord, NH to West Ossipeebus bus
    8h 2m
    $168–739

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

Calendar48Weekly Planes
Duration4h 29mAverage Duration
Ticket$81Cheapest Price
See schedules

Questions & Answers

What companies run services between Chicago, IL, USA and Ossipee, NH, USA?

You can take a bus from Chicago Bus Station to Ossipee via New York Midtown, Boston, Boston - South Station, and West Ossipee in around 29h 43m.

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

Trips from Chicago

Trips to Ossipee

Popular routes