Question 1

What is the cheapest day to depart on your flight to Portland, Maine?

Accepted Answer

On average, the least expensive day to fly to Portland, Maine from Chicago O'Hare Intl Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $309. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Thursday 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 $394.

Question 2

How far in advance should I book a flight to Portland, Maine?

Accepted Answer

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 $383 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 $288 on momondo.

Question 3

What day of the week experiences the fewest flight delays on this route?

Accepted Answer

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

Question 4

How many flights depart from Chicago O'Hare Intl Airport to Portland, Maine on average per week?

Accepted Answer

As of December 2025, there are 35 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 14% of flights taking off on this day.

Question 5

What airlines fly to Portland, Maine?

Accepted Answer

American Airlines, United 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. American Airlines is the first choice among our users, with 37% of people opting to fly with this airline when traveling to Portland, Maine. Keep in mind that there are 7 different airlines that fly to Portland, Maine on a routine basis, so you have a few additional options to choose from.

Question 6

Can stopping save me money on Chicago O'Hare Intl Airport to Portland, Maine flights?

Accepted Answer

You could potentially save up to 40% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Portland, Maine flight.

Question 7

What is the most punctual flight time for Chicago to Portland flights?

Accepted Answer

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

Question 8

How many flights depart from Chicago O'Hare Intl Airport to Portland, Maine on average per day?

Accepted Answer

As of December 2025, there are 5 flights per day flying from Chicago O'Hare Intl Airport to Portland, Maine. The most common time of day flights depart is 5:00PM, with 60% of flights taking off in the afternoon.

Question 9

How often are flights from Chicago to Portland delayed?

Accepted Answer

Historically, on average around 16% 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 131 minutes.

Question 10

How have Chicago O'Hare Intl Airport to Portland, Maine flight prices changed over time?

Accepted Answer

As of December 2025, prices for Chicago O'Hare Intl Airport to Portland, Maine flights are approximately 34% cheaper when compared to flights at the same time last year.

Question 11

Which airline has the best punctuality record on Chicago to Portland flights?

Accepted Answer

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 16% of their flights experiencing any sort of delay.

Question 12

What is the cheapest time of day to depart on your flight to Portland, Maine?

Accepted Answer

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 $320. 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 $374. Of course, these prices can vary depending on the time of year and what airport you fly to.

Question 13

What cabin class options are available on Chicago O'Hare Intl to Portland flights?

Accepted Answer

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

Question 14

What is the cheapest month to fly to Portland, Maine?

Accepted Answer

The cheapest month to fly to Portland, Maine from Chicago O'Hare Intl Airport is in September. Flight prices, which tend to average around $330, 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 September, then flying in March is also cheap. Prices for this month can be found on momondo for an average of $331.

Question 15

What is the cheapest Chicago O'Hare Intl to Portland flight route?

Accepted Answer

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

Question 16

What is the cheapest airline that flies from Chicago O'Hare Intl to Portland?

Accepted Answer

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

Question 17

When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Portland Airport?

Accepted Answer

Prices for flights from Chicago O'Hare Intl Airport to Portland Airport are updated daily.

Question 18

How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Portland Airport?

Accepted Answer

As of December 2025, there are 3 operators available to choose from for flights from Chicago O'Hare Intl Airport to Portland Airport.

Question 19

How old do you have to be to fly from Chicago O'Hare Intl Airport to Portland Airport?

Accepted Answer

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago O'Hare Intl Airport to Portland Airport.

Question 20

What documentation or ID do you need to fly to Portland Airport?

Accepted Answer

The travel and health documents you'll need for your trip to Portland Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Portland Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Best Price Found	$358
Fastest flight time	2h 24m
Direct flights	Every day
Airports in Portland, Maine	1 airport

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $163	Free Cancellation	Rating 7.9 8,007 reviews	Search Delta flights
United Airlines	PriceFrom $221	Free Cancellation	Rating 7.4 9,095 reviews	Search United Airlines flights
American Airlines	PriceFrom $231	Free Cancellation	Rating 7.2 11,050 reviews	Search American Airlines flights

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What is the cheapest month to fly to Portland, Maine?

What is the cheapest day to depart on your flight to Portland, Maine?

What is the cheapest time of day to depart on your flight to Portland, Maine?

What is the cheapest Chicago O'Hare Intl to Portland flight route?

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

How far in advance should I book a flight to Portland, Maine?

What cabin class options are available on Chicago O'Hare Intl to Portland flights?

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

Can stopping save me money on Chicago O'Hare Intl Airport to Portland, Maine flights?

You could potentially save up to 40% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Portland, Maine flight.

How have Chicago O'Hare Intl Airport to Portland, Maine flight prices changed over time?

As of December 2025, prices for Chicago O'Hare Intl Airport to Portland, Maine flights are approximately 34% cheaper when compared to flights at the same time last year.

What is the cheapest airline that flies from Chicago O'Hare Intl to Portland?

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

What airlines fly to Portland, Maine?

How often are flights from Chicago to Portland delayed?

Historically, on average around 16% 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 131 minutes.

What is the most punctual flight time for Chicago to Portland flights?

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

What day of the week experiences the fewest flight delays on this route?

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

Which airline has the best punctuality record on Chicago to Portland flights?

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 16% of their flights experiencing any sort of delay.

How many flights depart from Chicago O'Hare Intl Airport to Portland, Maine on average per day?

As of December 2025, there are 5 flights per day flying from Chicago O'Hare Intl Airport to Portland, Maine. The most common time of day flights depart is 5:00PM, with 60% of flights taking off in the afternoon.

How many flights depart from Chicago O'Hare Intl Airport to Portland, Maine on average per week?

As of December 2025, there are 35 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 14% of flights taking off on this day.

When to book flights from Chicago O'Hare Intl Airport to Portland, Maine

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How old do you have to be to fly from Chicago O'Hare Intl Airport to Portland Airport?

What documentation or ID do you need to fly to Portland Airport?

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