Question 1

How have Chicago to Portland, Maine flight prices changed over time?

Accepted Answer

As of December 2025, prices for Chicago to Portland, Maine flights are approximately 24% more expensive when compared to flights at the same time last year.

Question 2

Which layover airport offers the lowest fares from Chicago to Portland, Maine?

Accepted Answer

Flights via New York (JFK) offer the lowest average round-trip price of $183.

Question 3

How many flights depart from Chicago to Portland, Maine on average per week?

Accepted Answer

As of December 2025, there are 35 flights per week flying from Chicago to Portland, Maine. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.

Question 4

What is the cheapest airline that flies from Chicago to Portland?

Accepted Answer

Delta and Southwest are the most popular carriers operating from Chicago to Portland

Question 5

How many flights depart from Chicago to Portland, Maine on average per day?

Accepted Answer

The number of flights available between Chicago and Portland, Maine is 5 per day as of December 2025. The most frequent departure time is 5:00PM, with 60% of daily flights leaving in the afternoon.

Question 6

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

Accepted Answer

The cheapest month to fly to Portland, Maine from Chicago is in February. Flight prices, which tend to average around $285, 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 February, then flying in March is also cheap. Prices for this month can be found on momondo for an average of $309.

Question 7

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 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 8

Which layover airport has the shortest connection time from Chicago to Portland, Maine?

Accepted Answer

Detroit (DTW) has the shortest average layover time for this route: 0h 31m.

Question 9

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 at night have, in the past, seen delays more frequently in comparison.

Question 10

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 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 because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $394.

Question 11

What cabin class options are available on Chicago to Portland flights?

Accepted Answer

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

Question 12

Can stopping save me money on Chicago to Portland, Maine flights?

Accepted Answer

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

Question 13

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 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 14

Which layover airport has the shortest travel time from Chicago to Portland, Maine?

Accepted Answer

Flights connecting via Detroit (DTW) have the shortest average one-way travel time: 3h 32m.

Question 15

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

Accepted Answer

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 6% of their flights experiencing any sort of delay.

Question 16

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 17

Which airport is the most popular layover for flights between Chicago and Portland, Maine?

Accepted Answer

New York (JFK) was the most common stop: 67% of momondo users choosing 1-stop flights on this route connected there.

Question 18

How often are flights from Chicago to Portland delayed?

Accepted Answer

Historically, on average around 15% 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 127 minutes.

Question 19

What is the cheapest Chicago to Portland flight route?

Accepted Answer

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

Question 20

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 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 for as low as $288 on momondo.

Question 21

When did momondo last update prices for flights from Chicago to Portland Airport?

Accepted Answer

Prices for flights from Chicago to Portland Airport refresh daily.

Question 22

How many operators does momondo search for flights from Chicago to Portland Airport?

Accepted Answer

As of December 2025, there are 4 operators available to choose from for flights from Chicago to Portland Airport.

Question 23

How old do you have to be to fly from Chicago 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 to Portland Airport.

Question 24

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

Accepted Answer

The travel and health documents required for your trip to Portland Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Portland Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best Price Found	$358
Fastest flight time	2h 15m
Direct flights	Every day
Airports in Portland, Maine	1 airport

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $163	Free Cancellation	Rating 7.9 8,008 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
Southwest	PriceFrom $313	Free Cancellation	Rating 7.9 4,253 reviews	Search Southwest flights

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How to get the cheapest flight ticket from Chicago to Portland, Maine

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 to Portland flight route?

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

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

What cabin class options are available on Chicago to Portland flights?

There are 4 cabin classes available to choose from on Chicago 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 to Portland, Maine flights?

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

How have Chicago to Portland, Maine flight prices changed over time?

As of December 2025, prices for Chicago to Portland, Maine flights are approximately 24% more expensive when compared to flights at the same time last year.

What is the cheapest airline that flies from Chicago to Portland?

Delta and Southwest are the most popular carriers operating from Chicago to Portland

What airlines fly to Portland, Maine?

How often are flights from Chicago to Portland delayed?

Historically, on average around 15% 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 127 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 at night 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, Southwest have had the least number of delays on this route over the last 12 months; with about 6% of their flights experiencing any sort of delay.

Which airport is the most popular layover for flights between Chicago and Portland, Maine?

New York (JFK) was the most common stop: 67% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from Chicago to Portland, Maine?

Flights via New York (JFK) offer the lowest average round-trip price of $183.

Which layover airport has the shortest travel time from Chicago to Portland, Maine?

Flights connecting via Detroit (DTW) have the shortest average one-way travel time: 3h 32m.

Which layover airport has the shortest connection time from Chicago to Portland, Maine?

Detroit (DTW) has the shortest average layover time for this route: 0h 31m.

How many flights depart from Chicago to Portland, Maine on average per day?

The number of flights available between Chicago and Portland, Maine is 5 per day as of December 2025. The most frequent departure time is 5:00PM, with 60% of daily flights leaving in the afternoon.

How many flights depart from Chicago to Portland, Maine on average per week?

As of December 2025, there are 35 flights per week flying from Chicago 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 to Portland, Maine

Cheap Chicago to Portland, Maine (CHI to PWM) flight deals and tips

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When did momondo last update prices for flights from Chicago to Portland Airport?

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How old do you have to be to fly from Chicago to Portland Airport?

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

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What is the most popular airline from Chicago to Portland, Maine?

Best airlines flying from Chicago to Portland, Maine

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