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

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

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

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Portland (PWM)plane plane ORD - PWM
    4h 33m
    $128–435

  2. 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 38m
    $637–981

  3. 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, MA - South Station to Portland, MEbus bus
    28h 55m
    $247–377

  4. Drive  1,048.5 mi

    1. Drive from Chicago to Graycar car 1,048.5 mi
    19h 28m
    $180–259

  5. Fly Chicago Midway International Airport to Portland

    1. Fly from Chicago Midway International Airport (MDW) to Portland (PWM)plane plane MDW - PWM
    4h 11m
    $172–685

  6. 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 52m
    $200–765

  7. 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 11m
    $630–1,115

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

Calendar63Weekly Planes
Duration4h 14mAverage Duration
Ticket$69Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Gray.ExpandLaunch map view
  • Distance: 934 mi
  • Duration: 4h 33m

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

American Airlines, United Airlines, and Delta fly from Chicago O'Hare International Airport (ORD) to Portland (PWM) every 3 hours. Alternatively, you can take a bus from Chicago Bus Station to Gray via New York Midtown, Boston, Boston, MA - South Station, Ptc, and Yarmouth Town Hall in around 28h 55m.

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