Cheap flights from Portland, Maine to Chicago from $135

The month of April is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Portland, Maine averaging around $308.

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as $452. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Portland, Maine because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $621.

Flying to Chicago O'Hare Intl Airport from Portland, Maine in the evening is the least expensive time of day to depart. momondo users have found prices as low as $412 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $511. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Portland to Chicago O'Hare Intl for the best Portland - Chicago O'Hare Intl flight prices

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Portland, Maine when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $392 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Portland, Maine for as low as $304 on momondo.

There are 4 cabin classes available to choose from on Portland, Maine to Chicago O'Hare Intl Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

You could potentially save up to 27% on your flight if you consider stops on a Portland, Maine to Chicago O'Hare Intl Airport flight.

As of October 2026, prices for Portland, Maine to Chicago O'Hare Intl Airport flights are approximately 294% more expensive when compared to flights at the same time last year.

Delta is the most popular carrier operating from Portland to Chicago O'Hare Intl

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Portland, Maine according to our data. American Airlines is the first choice among our users, with 39% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 4 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

The number of flights available between Portland, Maine and Chicago O'Hare Intl Airport is 4 per day as of October 2026. The most frequent departure time is 1:00PM, with 64% of daily flights leaving in the afternoon.

The number of flights available between Portland, Maine and Chicago O'Hare Intl Airport is 33 per week as of October 2026. The most frequent departure day is Mon, with 27% of weekly flights leaving on this day.