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Flights from Chicago to Maine

Flight deals from Chicago to Maine

Looking for cheap tickets from Chicago to Maine, or a last-minute trip? Find the lowest prices on one-way and return tickets right here.
Portland.Rs56,415 per passenger.Departing Wed, 3 Sep, returning Thu, 4 Sep.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Wed, 3 Sep, arriving in Portland.Inbound direct flight with United departs from Portland on Thu, 4 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs56,415, select.
Bangor.Rs65,227 per passenger.Departing Mon, 22 Sep, returning Sat, 4 Oct.Return flight with American Airlines.Outbound direct flight with American Airlines departs from Chicago O'Hare International on Mon, 22 Sep, arriving in Bangor.Inbound direct flight with American Airlines departs from Bangor on Sat, 4 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs65,227, select.
Bar Harbor.Rs156,384 per passenger.Departing Fri, 3 Oct, returning Tue, 7 Oct.Return flight with Frontier Airlines and Cape Air.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Fri, 3 Oct, arriving in Bar Harbor.Inbound indirect flight with Cape Air, departs from Bar Harbor on Tue, 7 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From Rs156,384, select.
Augusta.Rs229,110 per passenger.Departing Fri, 29 Aug, returning Mon, 1 Sep.Return flight with Frontier Airlines and Cape Air.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Fri, 29 Aug, arriving in Augusta.Inbound indirect flight with Cape Air, departs from Augusta on Mon, 1 Sep, arriving in Chicago Midway.Price includes taxes and charges.From Rs229,110, select.
Rockland.Rs269,729 per passenger.Departing Tue, 26 Aug, returning Fri, 29 Aug.Return flight with Frontier Airlines and Cape Air.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 26 Aug, arriving in Rockland.Inbound indirect flight with Cape Air, departs from Rockland on Fri, 29 Aug, arriving in Chicago Midway.Price includes taxes and charges.From Rs269,729, select.

Flying from Chicago to Maine

Arm yourself with these facts on the fly.
Cheapest flight foundRs28,206, Portland
Cheapest month to flyAugust
Average flight time2 hrs, 24 mins
Cheapest airport to fly fromChicago Midway
Most popular airlineAmerican Airlines

Frequently asked questions

We looked at all of the upcoming return flights from Chicago to Maine we could find over the next 12 months. It looks like Rs55,945 is the best price. This is good, compared to the average Maine ticket price of Rs154,078.
The cheapest month to fly from Chicago to Rockland Airport is usually August. The cheapest month to fly from Chicago to Augusta Airport is usually August. The cheapest month to fly from Chicago to Bar Harbor Airport is usually October. And the cheapest month to fly from Chicago to Bangor Airport is usually September.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Maine on Wednesday, 3 September 2025.
Chicago O'Hare International Airport offers direct flights to Maine.
If you're flying from Chicago, the cheapest city in Maine to fly into is Portland. The cheapest airport serving Portland at the moment is Portland.
The average flight time between Chicago and Maine is 2 hours and 24 minutes.