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How to get fromChicago to Ogunquitby plane, bus, bus (Flixbus), train (Amtrak), car, train, or bus (Greyhound)

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There are 11 ways to get from Chicago to Ogunquit by plane, bus, bus (Flixbus), train (Amtrak), car, train, or bus (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. Fly Chicago Midway International Airport to Portland, bus

    best
    1. Fly from Chicago Midway International Airport (MDW) to Portland (PWM)plane plane MDW - PWM
    2. Take the bus from City of Portland to Wells Transportation Centerbus bus
    6h 34m
    $152–696

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

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Portland (PWM)plane plane ORD - PWM
    2. Take the bus from City of Portland to Wells Transportation Centerbus bus
    6h 59m
    $126–516

  3. Bus (Flixbus)

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2641 / ...
    2. Take the bus from New York Midtown to Portsmouth Bus Stopbus bus FlixBus N2615
    24h 40m
    $277–419

  4. Train (Amtrak)

    1. Take the train from Chicago Union Station to Bostontrain train Lake Shore Limited
    2. Take the train from Boston to Wellstrain train Downeaster
    25h 6m
    $388–746

  5. Drive 1,006.6 mi

    1. Drive from Chicago to Ogunquitcar car 1,006.6 mi
    18h 47m
    $184–266

  6. Fly Chicago Midway International Airport to Boston Logan Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane plane MDW - BOS
    2. Take the train from Woburn Amtrak Station to Wellstrain train
    7h 26m
    $158–592

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Boston Logan Airport (BOS)plane plane ORD - BOS
    2. Take the train from Woburn Amtrak Station to Wellstrain train
    7h 47m
    $132–482

  8. Fly Chicago Midway International Airport to Manchester Airport, bus, train

    1. Fly from Chicago Midway International Airport (MDW) to Manchester Airport (MHT)plane plane MDW - MHT
    2. Take the bus from Boston Manchester Airport to Bostonbus bus
    3. Take the train from Boston to Wellstrain train
    9h 27m
    $184–706

  9. Fly Chicago Midway International Airport to Theodore Francis Green State Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Theodore Francis Green State Airport (PVD)plane plane MDW - PVD
    2. Take the train from TF Green Airport to Rugglestrain train
    3. Take the train from Boston to Wellstrain train
    9h 32m
    $144–507

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Manchester Airport (MHT)plane plane ORD - MHT
    2. Take the bus from Boston Manchester Airport to Bostonbus bus
    3. Take the train from Boston to Wellstrain train
    10h
    $154–566

  11. Bus via Brook Park (Greyhound)

    1. Take the bus from Chicago Bus Station to Cleveland Bus Stationbus bus
    2. Take the bus from Cleveland Bus Station to Bostonbus bus
    3. Take the bus from Boston to Wells Transportation Centerbus bus
    24h 57m
    $189–350

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

Calendar19Weekly Planes
Duration3h 56mAverage Duration
Ticket$125Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Ogunquit.ExpandLaunch map view
  • Distance: 947.1 mi
  • Duration: 6h 34m

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

You can take a bus from Chicago Bus Station to Ogunquit via New York Midtown and Portsmouth Bus Stop in around 24h 40m. Alternatively, you can take a train from Chicago Union Station to Ogunquit via Boston, Back Bay, North Station, Boston, and Wells in around 25h 6m.

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