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

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There are 8 ways to get from Chicago to Gray by plane, train, bus, bus (Greyhound, Amtrak), car, 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 Chicago Midway International Airport to Portland

    best
    1. Fly from Chicago Midway International Airport (MDW) to Portland (PWM)plane plane MDW - PWM
    4h 11m
    $182–685

  2. Fly Chicago O'Hare International Airport to Portland

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Portland (PWM)plane plane ORD - PWM
    4h 37m
    $158–555

  3. 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 39m
    $407–782

  4. Bus via Brook Park

    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, MA - South Station to Portland, MEbus bus
    26h 3m
    $213–397

  5. Drive 1,048.5 mi

    1. Drive from Chicago to Graycar car 1,048.5 mi
    19h 28m
    $192–277

  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
    7h 17m
    $680–1,010

  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 59m
    $180–600

  8. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2641 / ...
    2. Take the bus from New York Midtown to City of Portlandbus bus FlixBus N2615
    26h 55m
    $232–374

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

Calendar19Weekly Planes
Duration3h 56mAverage Duration
Ticket$127Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Gray.ExpandLaunch map view
  • Distance: 922.2 mi
  • Duration: 4h 11m

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

Southwest Airlines flies from Chicago Midway International Airport (MDW) to Portland (PWM) 3 times a day. Alternatively, you can take a bus from Chicago Bus Station to Gray via Cleveland Bus Station, Boston, Boston, MA - South Station, Portland Transportation Center, and Yarmouth Town Hall in around 26h 3m.

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