Cheap flights from Chicago O'Hare Intl Airport to Portland from $85

The cheapest month to fly to Portland, Maine from Chicago O'Hare Intl Airport is in March. Flight prices, which tend to average around $301, are often lower during this time because this is during the off-season. If you aren’t able to travel to Portland, Maine during the month of March, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $321.

On average, the least expensive day to fly to Portland, Maine from Chicago O'Hare Intl Airport is on a Wednesday. momondo users have found tickets for Wednesday departures for as low as $337. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Sunday is the most expensive day to depart from Chicago O'Hare Intl Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $420.

In the evening is the cheapest time of day to fly from Chicago O'Hare Intl Airport to Portland, Maine when you can find flight prices for as low as $299. Flying to Portland, Maine in the evening is an ideal time because this is during off-peak travel hours. Try not to purchase tickets in the afternoon because they tend to be around $378. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

You are more likely to see cheaper flights to Portland, Maine from Chicago O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Portland, Maine for around $369 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Portland, Maine from Chicago O'Hare Intl Airport for as low as $282 on momondo.

There are 4 cabin classes available to choose from on Chicago O'Hare Intl Airport to Portland, Maine 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 6% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Portland, Maine flight.

As of June 2026, prices for Chicago O'Hare Intl Airport to Portland, Maine flights are approximately 368% more expensive when compared to flights at the same time last year.

JetBlue, United Airlines, and Delta are the most popular carriers operating from Chicago O'Hare Intl to Portland

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Portland, Maine from Chicago O'Hare Intl Airport according to our data. United Airlines is the first choice among our users, with 42% of people opting to fly with this airline when traveling to Portland, Maine. Keep in mind that there are 5 different airlines that fly to Portland, Maine on a routine basis, so you have a few additional options to choose from.

Historically, on average around 19% of flights between Chicago and Portland have experienced a delay on any given week. The average delay length over the past 12 months has been 136 minutes.

Generally, flights departing at night tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

Tuesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Saturday has historically seen more delays on average compared to the rest of the week.

According to our data, American Airlines have had the least number of delays on this route over the last 12 months; with about 17% of their flights experiencing any sort of delay.

As of June 2026, there are 7 flights per day flying from Chicago O'Hare Intl Airport to Portland, Maine. The most common time of day flights depart is 6:00PM, with 51% of flights taking off in the evening.

As of June 2026, there are 51 flights per week flying from Chicago O'Hare Intl Airport to Portland, Maine. The most common day of the week flights depart is Mon, with 18% of flights taking off on this day.