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

The number of flights available between Chicago and Portland, Maine is 8 per day as of August 2025. The most frequent departure time is 6:00PM, with 48% of daily flights leaving in the evening.

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 according to our data. American Airlines is the first choice among our users, with 36% 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.

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 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.

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

As of August 2025, there are 58 flights per week flying from Chicago to Portland, Maine. The most common day of the week flights depart is Fri, with 19% of flights taking off on this day.

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

United Airlines, Southwest, and JetBlue are the most popular carriers operating from Chicago to Portland

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.

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

Prices for flights from Chicago to Portland Airport refresh daily.

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

As of August 2025, there are 5 operators available to choose from for flights from Chicago to Portland Airport.

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

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

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.

$100 Cheap Flights from Chicago to Portland in 2025

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Find the cheapest flights from Chicago to Portland

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

6:15 am - 1:23 pmORD-PWM

6h 08m1 stop

6:10 am - 10:47 amPWM-ORD

5h 37m1 stop

$183JetBlue

Find Deal

Wed, Aug 27 - Sun, Aug 31

1:35 pm - 10:06 pmORD-PWM

7h 31m1 stop

7:30 am - 12:10 pmPWM-ORD

5h 40m1 stop

$193JetBlue

Find Deal

Wed, Oct 1 - Tue, Oct 7

8:13 pm - 11:59 pmORD-PWM

2h 46mnonstop

6:15 am - 8:11 amPWM-ORD

2h 56mnonstop

$208American Airlines

Find Deal

Sat, Aug 30 - Sat, Sep 6

8:05 am - 11:38 amORD-PWM

2h 33mnonstop

3:32 pm - 5:23 pmPWM-ORD

2h 51mnonstop

$217American Airlines

Find Deal

Mon, Aug 25 - Thu, Aug 28

7:15 am - 1:22 pmORD-PWM

5h 07m1 stop

6:23 pm - 8:23 pmPWM-ORD

3h 00mnonstop

$227United Airlines

Find Deal

Tue, Sep 9 - Sat, Sep 13

11:40 am - 2:55 pmMDW-PWM

2h 15mnonstop

5:45 am - 11:10 amPWM-MDW

6h 25m1 stop

$227Southwest

Find Deal

Tue, Sep 9 - Sat, Sep 13

6:10 pm - 9:44 pmORD-PWM

2h 34mnonstop

6:14 am - 8:05 amPWM-ORD

2h 51mnonstop

$230United Airlines

Find Deal

Thu, Oct 16 - Sat, Oct 18

11:40 am - 2:55 pmMDW-PWM

2h 15mnonstop

5:45 am - 1:30 pmPWM-MDW

8h 45m2 stops

$232Southwest

Find Deal

Tue, Sep 9 - Sat, Sep 13

7:00 am - 1:56 pmORD-PWM

5h 56m1 stop

2:36 pm - 9:53 pmPWM-ORD

8h 17m1 stop

$237Delta

Find Deal

Wed, Sep 3 - Sat, Sep 6

4:25 pm - 12:03 amMDW-PWM

6h 38m1 stop

11:48 am - 5:37 pmPWM-MDW

6h 49m1 stop

$237Delta

Find Deal

Wed, Sep 3 - Tue, Sep 9

Delta flights from Chicago to Portland, Maine

Our best Delta deals on Chicago to Portland, Maine flight tickets

Delta

Sep 3

ORD7:00 amChicago O'Hare Intl

5h 56m

1 stop

PWM1:56 pmPortland

Sep 6

PWM2:36 pmPortland

8h 17m

1 stop

ORD9:53 pmChicago O'Hare Intl

$237

Find similar

Delta

Aug 23

ORD2:25 pmChicago O'Hare Intl

8h 38m

2 stops

PWM12:03 amPortland

Aug 30

PWM5:30 pmPortland

7h 26m

1 stop

ORD11:56 pmChicago O'Hare Intl

$240

Find similar

Delta

Sep 3

MDW4:25 pmChicago Midway

6h 38m

1 stop

PWM12:03 amPortland

Sep 6

PWM7:00 amPortland

9h 28m

2 stops

MDW3:28 pmChicago Midway

$242

Find similar

American Airlines flights from Chicago to Portland, Maine

Our best American Airlines deals on Chicago to Portland, Maine flight tickets

American Airlines

Aug 30

ORD8:13 pmChicago O'Hare Intl

2h 46m

PWM11:59 pmPortland

Sep 6

PWM6:15 amPortland

2h 56m

ORD8:11 amChicago O'Hare Intl

$208

Find similar

American Airlines

Aug 25

ORD8:05 amChicago O'Hare Intl

2h 33m

PWM11:38 amPortland

Aug 28

PWM3:32 pmPortland

2h 51m

ORD5:23 pmChicago O'Hare Intl

$217

Find similar

American Airlines

Aug 23

ORD3:32 pmChicago O'Hare Intl

5h 13m

1 stop

PWM9:45 pmPortland

Aug 30

PWM6:30 amPortland

3h 02m

ORD8:32 amChicago O'Hare Intl

$225

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 8/27

6:15 am-1:23 pm

1 stop6h 08m

Portland

Sun 8/31

6:10 am-10:47 am

1 stop5h 37m

$183

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 10/1

1:35 pm-10:06 pm

1 stop7h 31m

Portland

Tue 10/7

7:30 am-12:10 pm

1 stop5h 40m

$193

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 8/30

8:13 pm-11:59 pm

Nonstop2h 46m

Portland

Sat 9/6

6:15 am-8:11 am

Nonstop2h 56m

$208

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Mon 8/25

8:05 am-11:38 am

Nonstop2h 33m

Portland

Thu 8/28

3:32 pm-5:23 pm

Nonstop2h 51m

$217

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 9/9

7:15 am-1:22 pm

1 stop5h 07m

Portland

Sat 9/13

6:23 pm-8:23 pm

Nonstop3h 00m

$227

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 9/9

11:40 am-2:55 pm

Nonstop2h 15m

Portland

Sat 9/13

5:45 am-11:10 am

1 stop6h 25m

$227

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 10/16

6:10 pm-9:44 pm

Nonstop2h 34m

Portland

Sat 10/18

6:14 am-8:05 am

Nonstop2h 51m

$230

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 9/9

11:40 am-2:55 pm

Nonstop2h 15m

Portland

Sat 9/13

5:45 am-1:30 pm

2 stops8h 45m

$232

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 9/3

7:00 am-1:56 pm

1 stop5h 56m

Portland

Sat 9/6

2:36 pm-9:53 pm

1 stop8h 17m

$237

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Wed 9/3

4:25 pm-12:03 am

1 stop6h 38m

Portland

Tue 9/9

11:48 am-5:37 pm

1 stop6h 49m

$237

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How to get the cheapest flight ticket from Chicago 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

Layovers

Other information

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

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 $303.

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 is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $324. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Friday 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 $401.

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 to Portland, Maine when you can find flight prices for as low as $304. 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 morning because they tend to be around $376. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Chicago to Portland flight route?

Fly from Chicago Midway to Portland for the best Chicago - 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 when booking weeks ahead of your departure date. In general, you can expect to find flights to Portland, Maine for around $394 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 $282 on momondo.

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?

No. A direct flight is the cheapest option for a flight between Chicago to Portland, Maine.

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

As of August 2025, prices for Chicago to Portland, Maine flights are approximately 53% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to Portland, Maine

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

Estimated round-trip price

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

Find info about flight duration, direct flights, and airports for your flight from Chicago to Portland, Maine

Best Price Found	$100
Fastest flight time	2h 10m
Direct flights	Every day
Airports in Portland, Maine	1 airport

The best one-way flight to Portland, Maine from Chicago in the past 72 hours is $100. The best round-trip flight deal from Chicago to Portland, Maine found on momondo in the last 72 hours is $183.

The fastest flight from Chicago to Portland, Maine takes 2h 10m

Direct flights go from Chicago to Portland, Maine every day.

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

Search flight deals

How far is Chicago to Portland by plane?
Chicago and Portland are 887.4 mi apart from one another. By plane, this route typically takes 2h 10m.
When did momondo last update prices for flights from Chicago to Portland Airport?
Prices for flights from Chicago to Portland Airport refresh daily.
How many operators does momondo search for flights from Chicago to Portland Airport?
As of August 2025, there are 5 operators available to choose from for flights from Chicago to Portland Airport.
How old do you have to be to fly from Chicago 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 to Portland Airport.
What documentation or ID do you need to fly to Portland Airport?
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.
What is the most popular plane model from Chicago to Portland, Maine?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to Portland, Maine is Embraer 175 (22.12% of total bookings). The next most popular plane models are Boeing 737-800 (17.33%), Boeing 737-700 (14.03%), and Embraer 175 (Enhanced Winglets) (13.79%).
What is the most popular airline from Chicago to Portland, Maine?
momondo data reveals that the most frequently booked airline on the route from Chicago to Portland, Maine is United Airlines, representing 55% of all bookings. The subsequent popular airlines are American Airlines at 29%, Southwest at 9%, and Frontier at 4%.

Best airlines flying from Chicago to Portland, Maine

Compare and see reviews for airlines that fly from Chicago to Portland, Maine with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $68	Free Cancellation	Rating 5.8 3,241 reviews	Search Frontier flights
Delta	PriceFrom $163	Free Cancellation	Rating 8.0 7,983 reviews	Search Delta flights
Southwest	PriceFrom $191	Free Cancellation	Rating 8.0 4,246 reviews	Search Southwest flights
American Airlines	PriceFrom $203	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom $213	Free Cancellation	Rating 7.4 8,904 reviews	Search United Airlines flights

Southwest Flights From Chicago to Portland, Maine
Across 3 Southwest flights from Chicago to Portland, Maine this week, the average price was $406, with the best Southwest deals starting from $191 round-trip. 4,246 users have rated Southwest on momondo, with an average score of 8.0/10.
United Airlines Flights From Chicago to Portland, Maine
United Airlines is also a popular choice for this route. United Airlines flight deals for Chicago to Portland, Maine start from as low as $213 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around $388. United Airlines operates 15 flights to Portland, Maine from Chicago in an average week. Users have rated it 7.4/10 across 8,904 reviews.

North Conway

Boothbay Harbor

Jackson

Conway

Freeport

Bartlett

Lewiston

Gorham

Brunswick

Auburn

Intervale

Windham

Falmouth

Bath

Georgetown

Oxford

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?

Yes. All flights to Portland from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

momondo helps you find the best flight between Chicago and Portland by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Yes. momondo can track prices for Chicago to Portland flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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.

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Cheap flights from Chicago to Portland from $100

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Portland departing on 10/31. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Big names and deals

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Filter for what you want

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Find the cheapest flights from Chicago to Portland

Cheap round-trip flights

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Cheap direct flights

Delta flights from Chicago to Portland, Maine

Our best Delta deals on Chicago to Portland, Maine flight tickets

American Airlines flights from Chicago to Portland, Maine

Our best American Airlines deals on Chicago to Portland, Maine flight tickets

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How to get the cheapest flight ticket from Chicago 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 to Portland flight route?

Fly from Chicago Midway 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?

No. A direct flight is the cheapest option for a flight between Chicago to Portland, Maine.

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

As of August 2025, prices for Chicago to Portland, Maine flights are approximately 53% cheaper when compared to flights at the same time last year.

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

United Airlines, Southwest, and JetBlue are the most popular carriers operating from Chicago to Portland

What airlines fly to Portland, Maine?

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 8 per day as of August 2025. The most frequent departure time is 6:00PM, with 48% of daily flights leaving in the evening.

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

As of August 2025, there are 58 flights per week flying from Chicago to Portland, Maine. The most common day of the week flights depart is Fri, with 19% 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

Find info about flight duration, direct flights, and airports for your flight from Chicago to Portland, Maine

Best Price Found

Fastest flight time

Direct flights

Airports in Portland, Maine

How far is Chicago to Portland by plane?

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

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

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?

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

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

Best airlines flying from Chicago to Portland, Maine

Compare and see reviews for airlines that fly from Chicago to Portland, Maine with momondo

Southwest Flights From Chicago to Portland, Maine

United Airlines Flights From Chicago 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