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How to get fromOld Orchard Beach to Chicagoby plane, train (Amtrak), bus (Amtrak, Greyhound), car, train, bus, or bus (Flixbus)

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

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 Portland to Chicago Midway International Airport

    best
    1. Fly from Portland (PWM) to Chicago Midway International Airport (MDW)plane plane PWM - MDW
    5h 48m
    $110–510

  2. Fly Portland to Chicago O'Hare International Airport

    cheapest
    1. Fly from Portland (PWM) to Chicago O'Hare International Airport (ORD)plane plane PWM - ORD
    6h 19m
    $95–440

  3. Train (Amtrak)

    1. Take the train from Old Orchard Beach Amtrak to Bostontrain train Downeaster
    2. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    25h 43m
    $367–771

  4. Bus via Brook Park

    1. Take the bus from Portland, ME to Boston, MA - 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
    25h 49m
    $175–372

  5. Drive 1,024.7 mi

    1. Drive from Old Orchard Beach to Chicagocar car 1,024.7 mi
    19h 6m
    $187–271

  6. Train to Boston Logan Airport, fly to Chicago Midway International Airport

    1. Take the train from Old Orchard Beach Amtrak to Woburn Amtrak Stationtrain train
    2. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    7h 3m
    $121–474

  7. Train to Boston Logan Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Old Orchard Beach Amtrak to Woburn Amtrak Stationtrain train
    2. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    7h 28m
    $641–974

  8. Train, bus to Manchester Airport, fly to Chicago Midway International Airport

    1. Take the train from Old Orchard Beach Amtrak to Bostontrain train
    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
    8h 42m
    $137–542

  9. Bus

    1. Take the bus from City of Portland to New York Midtownbus bus FlixBus N2615
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    27h 9m
    $197–332

Old Orchard Beach to Chicago by train and subway (Amtrak)

Calendar7Weekly Services
Duration25h 43mAverage Duration
Ticket$367Cheapest Price
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Questions & Answers

Map of how to get from Old Orchard Beach to Chicago.ExpandLaunch map view
  • Distance: 921.7 mi
  • Duration: 5h 48m

What companies run services between Old Orchard Beach, ME, USA and Chicago, IL, USA?

Southwest Airlines flies from Portland (PWM) to Chicago Midway International Airport (MDW) twice daily. Alternatively, you can take a train from Old Orchard Beach Amtrak to Chicago Union Station via Boston, North Station, Back Bay, and Boston in around 25h 43m.

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