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How to get fromChicago to Wolfeboroby plane, car, train, taxi or bus

Find Transport to Wolfeboro

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There are 9 ways to get from Chicago to Wolfeboro by plane, car, train, taxi, 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, drive

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Portland (PWM)plane plane ORD - PWM
    2. Drive from Portland-Airport-PWM to Wolfeborocar car
    5h 40m
    $88–421

  2. 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 Wolfeborotaxi taxi
    25h 32m
    $335–863

  3. Bus, taxi

    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 Meredithbus bus
    4. Take the taxi from Meredith to Wolfeborotaxi taxi
    29h 46m
    $319–524

  4. Drive 991.5 mi

    1. Drive from Chicago to Wolfeborocar car 991.5 mi
    18h 10m
    $181–262

  5. Fly Chicago Midway International Airport to Portland, drive

    1. Fly from Chicago Midway International Airport (MDW) to Portland (PWM)plane plane MDW - PWM
    2. Drive from Portland-Airport-PWM to Wolfeborocar car
    5h 17m
    $112–571

  6. Fly Chicago Midway International Airport to Manchester Airport, taxi

    1. Fly from Chicago Midway International Airport (MDW) to Manchester Airport (MHT)plane plane MDW - MHT
    2. Take the taxi from Concord to Wolfeborotaxi taxi
    6h 19m
    $372–972

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

    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 Doverbus bus
    3. Take the taxi from Dover to Wolfeborotaxi taxi
    7h 18m
    $328–642

  8. Fly Chicago Midway International Airport to Boston Logan Airport, bus, taxi

    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 Doverbus bus
    3. Take the taxi from Dover to Wolfeborotaxi taxi
    6h 54m
    $328–882

  9. Fly Chicago O'Hare International Airport to Manchester Airport, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Manchester Airport (MHT)plane plane ORD - MHT
    2. Take the taxi from Concord to Wolfeborotaxi taxi
    7h 3m
    $342–772

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

Calendar48Weekly Planes
Duration4h 29mAverage Duration
Ticket$76Cheapest Price
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Questions & Answers

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

There is no direct connection from Chicago to Wolfeboro. However, you can take the subway to O'Hare, walk to Chicago O'Hare International Airport (ORD) airport, fly to Portland (PWM), then drive to Wolfeboro. Alternatively, you can take the train to Boston, walk to Back Bay, take the subway to North Station, walk to Boston, take the train to Dover, then take the taxi to Wolfeboro.

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