Cheap Flights from Chicago (ORD) to Wiscasset (ISS)

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Wiscasset, ME (ISS)

  • notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
  • deals illustration

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • trophy illustration

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Alternative airports near Wiscasset

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Augusta State AUG. Cheapest option available. Average driving time to city center is 37 minutes. Flights from $344
AUG
Augusta State
Cheapest
Average driving time to city center37 min
Flights from $344

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Wiscasset, ME (ISS) cost?
Get a cheap one-way flight or cheap return flight from O'Hare Intl. Airport (ORD) to Wiscasset, ME (ISS) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Wiscasset, ME (ISS)?
Planning your getaway for may help you find better deals, as it's the cheapest month for flights between ORD and ISS. You'll often find the lowest fares during off-peak months.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to Wiscasset, ME (ISS)?
To find the cheapest airline that'll fly you from ORD to ISS, use Expedia's filter tool. Customize your search based on your travel needs, such as preferred carriers and number of stops. You can then sort your results by "Price (lowest to highest)" to see the cheapest fares upfront.
How many flights per day from O'Hare Intl. Airport (ORD) to Wiscasset, ME (ISS)?
There are no daily nonstop flights available from O'Hare Intl. Airport (ORD) to Wiscasset, ME (ISS). But you can book flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be soaring above the clouds in no time.
What day of the week has the most flights from ORD to ISS?
Friday is generally the busiest day for flights, while Tuesday tends to be the quietest.* Just remember that flight schedules can vary depending on various factors, including the time of year and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Wiscasset, ME (ISS)?
To arrive at Wiscasset, ME (ISS) on time, opt for a flight that leaves O'Hare Intl. Airport (ORD) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Wiscasset from O'Hare Intl. Airport (ORD)?
Portland Intl. Jetport Airport (PWM) is the only airport in Wiscasset with direct flights from O'Hare Intl. Airport (ORD). Explore your options and discover affordable fares on Expedia.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Wiscasset, ME (ISS) last-minute?
Holding off until just before your departure to book a flight from ORD to ISS often results in higher prices. While you might find some last-minute offers, they're not always guaranteed. Keep your travel plans flexible to boost your chances of scoring a bargain.
Is it cheaper to book an ORD to ISS flight and hotel package?
You can save money by booking an ORD to ISS flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage everything in one place. Once you've chosen your preferred flights and accommodations, consider adding extras such as activities, car rentals and tours.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Wiscasset, ME (ISS)?
You can usually reschedule or cancel your ORD to ISS flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find more information on our Customer Service portal.

Travel information

Origin airport
O'Hare Intl.
Destination airport
Wiscasset
Distance
927 mi

Book with confidence

Chicago to Wiscasset Flights

The cheapest times to fly from Chicago to Wiscasset

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Wiscasset are during the month of . You can find some of the cheapest flights from Chicago to Wiscasset with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Wiscasset

Sunday is one of the best days to book for cheap flights from Chicago to Wiscasset: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Wiscasset

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Wiscasset in 2025. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Wiscasset flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Wiscasset airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Wiscasset Flights

Explore a world of travel with Expedia

*Available to One Key members.