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 130 minutes.

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

Generally, flights departing at night 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, SkyWest Airlines have had the least number of delays on this route over the last 12 months; with no flights being classified as delayed.

What airlines fly to Portland, Maine?

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.

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

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

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

As of October 2025, 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 55% of flights taking off in the evening.

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

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

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

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

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

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.

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

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.

$113 Cheap Flights from Chicago O'Hare Intl Airport to Portland, Maine in 2025/26

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

As of October 2025, there are 54 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 17% of flights taking off on this day.

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Find the cheapest flights from Chicago O'Hare Intl Airport to Portland

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Cheap round-trip flights

Enter your travel dates to find the best prices.

11:19 am - 11:54 pmORD-PWM

11h 35m2 stops

6:00 am - 12:04 pmPWM-ORD

7h 04m1 stop

$244Delta

Find Deal

Tue, Nov 11 - Sat, Nov 15

7:10 am - 1:56 pmORD-PWM

5h 46m1 stop

4:10 pm - 6:18 pmPWM-ORD

3h 08mnonstop

$245United Airlines

Find Deal

Tue, Jan 6 - Sat, Jan 10

5:23 am - 12:30 pmORD-PWM

6h 07m1 stop

1:25 pm - 6:51 pmPWM-ORD

6h 26m1 stop

$249Delta

Find Deal

Sun, Nov 9 - Wed, Nov 12

8:55 am - 4:07 pmORD-PWM

6h 12m1 stop

6:00 am - 3:04 pmPWM-ORD

10h 04m2 stops

$254Delta

Find Deal

Mon, Nov 10 - Sat, Nov 15

6:41 pm - 9:07 amORD-PWM

13h 26m1 stop

5:06 pm - 9:23 pmPWM-ORD

29h 17m2 stops

$255Multiple Airlines

Find Deal

Sun, Jan 11 - Mon, Jan 12

5:40 am - 10:49 amORD-PWM

28h 09m1 stop

6:18 pm - 10:58 amPWM-ORD

17h 40m2 stops

$256Multiple Airlines

Find Deal

Thu, Jan 15 - Sat, Jan 17

11:48 am - 3:14 pmORD-PWM

2h 26mnonstop

5:45 am - 7:57 amPWM-ORD

3h 12mnonstop

$257United Airlines

Find Deal

Sun, Feb 15 - Thu, Feb 19

1:45 pm - 11:36 pmORD-PWM

8h 51m1 stop

2:20 pm - 10:59 pmPWM-ORD

9h 39m1 stop

$258JetBlue

Find Deal

Fri, Apr 10 - Wed, Apr 15

6:00 am - 12:54 pmORD-PWM

5h 54m1 stop

5:20 pm - 9:14 pmPWM-ORD

4h 54m1 stop

$277American Airlines

Find Deal

Thu, Dec 25 - Thu, Jan 1

11:45 am - 6:03 pmORD-PWM

5h 18m1 stop

5:07 pm - 9:19 pmPWM-ORD

5h 12m1 stop

$312American Airlines

Find Deal

Sun, Feb 15 - Tue, Feb 17

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

Our best Delta deals on Chicago O'Hare Intl Airport to Portland, Maine flight tickets

Delta

Nov 11

ORD11:19 amChicago O'Hare Intl

11h 35m

2 stops

PWM11:54 pmPortland

Nov 15

PWM6:00 amPortland

7h 04m

1 stop

ORD12:04 pmChicago O'Hare Intl

$244

Find similar

Delta

Nov 9

ORD5:23 amChicago O'Hare Intl

6h 07m

1 stop

PWM12:30 pmPortland

Nov 12

PWM1:25 pmPortland

6h 26m

1 stop

ORD6:51 pmChicago O'Hare Intl

$249

Find similar

Delta

Nov 10

ORD8:55 amChicago O'Hare Intl

6h 12m

1 stop

PWM4:07 pmPortland

Nov 15

PWM6:00 amPortland

10h 04m

2 stops

ORD3:04 pmChicago O'Hare Intl

$254

Find similar

United Airlines flights from Chicago O'Hare Intl Airport to Portland, Maine

Our best United Airlines deals on Chicago O'Hare Intl Airport to Portland, Maine flight tickets

United Airlines

Jan 6

ORD7:10 amChicago O'Hare Intl

5h 46m

1 stop

PWM1:56 pmPortland

Jan 10

PWM4:10 pmPortland

3h 08m

ORD6:18 pmChicago O'Hare Intl

$245

Find similar

United Airlines

Feb 15

ORD11:48 amChicago O'Hare Intl

2h 26m

PWM3:14 pmPortland

Feb 19

PWM5:45 amPortland

3h 12m

ORD7:57 amChicago O'Hare Intl

$257

Find similar

United Airlines

Nov 7

ORD10:53 amChicago O'Hare Intl

2h 19m

PWM2:12 pmPortland

Nov 10

PWM5:00 pmPortland

2h 55m

ORD6:55 pmChicago O'Hare Intl

$259

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Portland, Maine that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 11/11

11:19 am-11:54 pm

2 stops11h 35m

Portland

Sat 11/15

6:00 am-12:04 pm

1 stop7h 04m

$244

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 1/6

7:10 am-1:56 pm

1 stop5h 46m

Portland

Sat 1/10

4:10 pm-6:18 pm

Nonstop3h 08m

$245

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 11/9

5:23 am-12:30 pm

1 stop6h 07m

Portland

Wed 11/12

1:25 pm-6:51 pm

1 stop6h 26m

$249

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Mon 11/10

8:55 am-4:07 pm

1 stop6h 12m

Portland

Sat 11/15

6:00 am-3:04 pm

2 stops10h 04m

$254

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 1/11

6:41 pm-9:07 am

1 stop13h 26m

Portland

Mon 1/12

5:06 pm-9:23 pm

2 stops29h 17m

$255

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 1/15

5:40 am-10:49 am

1 stop28h 09m

Portland

Sat 1/17

6:18 pm-10:58 am

2 stops17h 40m

$256

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 2/15

11:48 am-3:14 pm

Nonstop2h 26m

Portland

Thu 2/19

5:45 am-7:57 am

Nonstop3h 12m

$257

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 4/10

1:45 pm-11:36 pm

1 stop8h 51m

Portland

Wed 4/15

2:20 pm-10:59 pm

1 stop9h 39m

$258

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 12/25

6:00 am-12:54 pm

1 stop5h 54m

Portland

Thu 1/1

5:20 pm-9:14 pm

1 stop4h 54m

$277

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 2/15

11:45 am-6:03 pm

1 stop5h 18m

Portland

Tue 2/17

5:07 pm-9:19 pm

1 stop5h 12m

$312

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Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago O'Hare Intl Airport to Portland, Maine

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Delays

Other information

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

The cheapest month to fly to Portland, Maine from Chicago O'Hare Intl Airport is in September. Flight prices, which tend to average around $329, 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.

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

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 $338. 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 $398.

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

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 $377. Of course, these prices can vary depending on the time of year and what airport you fly to.

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?

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 $402 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 $286 on momondo.

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 22% 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 October 2025, prices for Chicago O'Hare Intl Airport to Portland, Maine flights are approximately 7% cheaper when compared to flights at the same time last year.

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

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago O'Hare Intl Airport to Portland, Maine according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago O'Hare Intl Airport to Portland, Maine (ORD to PWM) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Portland, Maine

Best Price Found	$230
Fastest flight time	2h 17m
Direct flights	Every day
Airports in Portland, Maine	1 airport

The best one-way flight to Portland, Maine from Chicago O'Hare Intl Airport in the past 72 hours is $230. The best round-trip flight deal from Chicago O'Hare Intl Airport to Portland, Maine found on momondo in the last 72 hours is $391.

The fastest flight from Chicago O'Hare Intl Airport to Portland, Maine takes 2h 17m

Direct flights go from Chicago O'Hare Intl Airport to Portland, Maine every day.

There is 1 airport near Portland, Maine: Portland (PWM)

Search flight deals

How far is Chicago O'Hare Intl to Portland by plane?
Chicago O'Hare Intl and Portland are 899.6 mi apart from one another. By plane, this route typically takes 2h 19m.
When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Portland Airport?
Prices for flights from Chicago O'Hare Intl Airport to Portland Airport are updated daily.
How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Portland Airport?
As of October 2025, there are 3 operators available to choose from for flights from Chicago O'Hare Intl Airport to Portland Airport.
How old do you have to be to fly from Chicago O'Hare Intl Airport to Portland Airport?
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.
What documentation or ID do you need to fly to Portland Airport?
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.
What is the most popular plane model from Chicago O'Hare Intl Airport to Portland, Maine?
Based on momondo bookings for flights between Chicago O'Hare Intl Airport and Portland, Maine, the leading plane model is Boeing 737-800, making up 21.40% of the total bookings. Other popular models include Embraer 175 with 19.54%, Embraer 175 (Enhanced Winglets) with 17.15%, and Canadair (Bombardier) Regional Jet 700 with 15.36%.
What is the most popular airline from Chicago O'Hare Intl Airport to Portland, Maine?
momondo data reveals that the most frequently booked airline on the route from Chicago O'Hare Intl Airport to Portland, Maine is United Airlines, representing 63% of all bookings. The subsequent popular airlines are American Airlines at 35% and Delta at 2%.

Best airlines flying from Chicago O'Hare Intl Airport to Portland, Maine

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Portland, Maine with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $163	Free Cancellation	Rating 7.9 7,996 reviews	Search Delta flights
United Airlines	PriceFrom $226	Free Cancellation	Rating 7.4 8,997 reviews	Search United Airlines flights
American Airlines	PriceFrom $232	Free Cancellation	Rating 7.2 11,033 reviews	Search American Airlines flights

United Airlines Flights From Chicago O'Hare Intl Airport to Portland, Maine
United Airlines flight deals from Chicago O'Hare Intl Airport to Portland, Maine start from $226 round-trip. Over the 12 United Airlines flights for this route in a normal week, average airfare is usually $381 round-trip - but some users have found much cheaper deals with momondo.
American Airlines Flights From Chicago O'Hare Intl Airport to Portland, Maine
The best American Airlines deal for Chicago O'Hare Intl Airport to Portland, Maine flight tickets found on momondo in the last 72 hours was $232, round-trip. It should be noted that an average American Airlines flight deal for this route in this time was higher, at $352 round-trip. American Airlines operates 18 flights out of Chicago O'Hare Intl Airport into Portland, Maine in an average week, so prices vary by time and availability. 11,033 American Airlines reviews by users on momondo have scored the airline at 7.2/10.

North Conway

Boothbay Harbor

Jackson

Conway

Freeport

Lewiston

Brunswick

Bartlett

Auburn

Gorham

Intervale

Windham

Oxford

Bath

Georgetown

Falmouth

Tamworth

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Portland?

It is quick and easy to find Chicago to Portland flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Portland that suits you.

Can I find flights from Chicago to Portland with flexible booking policies on momondo?

momondo does allow users to show only those flights to Portland from Chicago which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Chicago to Portland?

Once you have performed a search for Chicago to Portland flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Chicago to Portland right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Portland, momondo offers a useful price alert feature which will track prices for flights to Portland from Chicago and alert you when they change.

An easier way to manage your Portland, Maine trip

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Cheap flights from Chicago O'Hare Intl Airport to Portland from $113

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

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United Airlines flights from Chicago O'Hare Intl Airport to Portland, Maine

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How to get the cheapest flight ticket from Chicago O'Hare Intl Airport to Portland, Maine

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

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 22% 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 October 2025, prices for Chicago O'Hare Intl Airport to Portland, Maine flights are approximately 7% 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, United Airlines, and American Airlines are the most popular carriers 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 130 minutes.

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

Generally, flights departing at night 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, SkyWest Airlines have had the least number of delays on this route over the last 12 months; with no flights being classified as delayed.

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

As of October 2025, 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 55% of flights taking off in the evening.

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

As of October 2025, there are 54 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 17% of flights taking off on this day.

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

Cheap Chicago O'Hare Intl Airport to Portland, Maine (ORD to PWM) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Portland, Maine

Best Price Found

Fastest flight time

Direct flights

Airports in Portland, Maine

How far is Chicago O'Hare Intl to Portland by plane?

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

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

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?

What is the most popular plane model from Chicago O'Hare Intl Airport to Portland, Maine?

What is the most popular airline from Chicago O'Hare Intl Airport to Portland, Maine?

Best airlines flying from Chicago O'Hare Intl Airport to Portland, Maine

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Portland, Maine with momondo

United Airlines Flights From Chicago O'Hare Intl Airport to Portland, Maine

American Airlines Flights From Chicago O'Hare Intl Airport to Portland, Maine

Traveling to a place near Portland?

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Portland?

Can I find flights from Chicago to Portland with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to Portland?

I’m not ready to book a flight from Chicago to Portland right now. Can momondo alert me if prices change?

An easier way to manage your Portland, Maine trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Airports servicing Maine