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

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

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 offers the lowest fares from Chicago to Portland, Maine?

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

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

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

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 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.

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

As of September 2025, there are 75 flights per week flying from Chicago to Portland, Maine. The most common day of the week flights depart is Mon, with 16% of flights taking off on this day.

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

The number of flights available between Chicago and Portland, Maine is 10 per day as of September 2025. The most frequent departure time is 6:00PM, with 46% of daily flights leaving in the evening.

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 September 2025, there are 4 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.

$96 Cheap Flights from Chicago to Portland in 2025/26

Q: What is the typical price of a round-trip flight between Chicago and Portland, Maine?

Prices are currently low for flights on this route. Typical prices usually range from $274 to $374. The lowest price recently found on this route was $238.

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Find the cheapest flights from Chicago to Portland

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

7:58 am - 11:28 amORD-PWM

2h 30mnonstop

3:38 pm - 9:10 pmPWM-ORD

6h 32m1 stop

$238American Airlines

Find Deal

Fri, Oct 31 - Fri, Oct 31

1:45 pm - 9:35 pmORD-PWM

6h 50m1 stop

5:37 pm - 7:50 pmPWM-ORD

3h 13mnonstop

$241American Airlines

Find Deal

Wed, Nov 12 - Sat, Nov 15

6:00 am - 12:30 pmMDW-PWM

5h 30m1 stop

12:48 pm - 6:08 pmPWM-MDW

6h 20m1 stop

$251Delta

Find Deal

Wed, Nov 12 - Sat, Nov 15

6:45 am - 1:22 pmORD-PWM

5h 37m1 stop

7:09 am - 6:23 pmPWM-ORD

12h 14m1 stop

$253JetBlue

Find Deal

Tue, Sep 30 - Sat, Oct 4

6:45 am - 12:08 pmORD-PWM

4h 23m1 stop

2:30 pm - 8:29 pmPWM-ORD

6h 59m2 stops

$256Delta

Find Deal

Wed, Nov 12 - Sat, Nov 15

1:35 pm - 10:06 pmORD-PWM

7h 31m1 stop

7:09 am - 6:23 pmPWM-ORD

12h 14m1 stop

$263JetBlue

Find Deal

Wed, Oct 1 - Sat, Oct 4

6:10 pm - 9:44 pmORD-PWM

2h 34mnonstop

5:41 pm - 11:30 pmPWM-ORD

6h 49m1 stop

$265United Airlines

Find Deal

Wed, Oct 1 - Tue, Oct 7

10:53 am - 2:12 pmORD-PWM

2h 19mnonstop

4:54 pm - 6:55 pmPWM-ORD

3h 01mnonstop

$269United Airlines

Find Deal

Tue, Nov 4 - Fri, Nov 7

5:05 am - 11:10 amMDW-PWM

5h 05m1 stop

3:30 pm - 9:05 pmPWM-MDW

6h 35m1 stop

$275Southwest

Find Deal

Fri, Nov 14 - Tue, Nov 18

7:10 pm - 10:25 pmMDW-PWM

2h 15mnonstop

2:40 pm - 4:15 pmPWM-MDW

2h 35mnonstop

$279Southwest

Find Deal

Sun, Sep 28 - Fri, Oct 3

American Airlines flights from Chicago to Portland, Maine

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

American Airlines

Oct 31

ORD7:58 amChicago O'Hare Intl

2h 30m

PWM11:28 amPortland

Oct 31

PWM3:38 pmPortland

6h 32m

1 stop

ORD9:10 pmChicago O'Hare Intl

$238

Find similar

American Airlines

Nov 12

ORD1:45 pmChicago O'Hare Intl

6h 50m

1 stop

PWM9:35 pmPortland

Nov 15

PWM5:37 pmPortland

3h 13m

ORD7:50 pmChicago O'Hare Intl

$241

Find similar

American Airlines

Nov 12

ORD6:06 amChicago O'Hare Intl

4h 40m

1 stop

PWM11:46 amPortland

Nov 15

PWM7:02 amPortland

6h 24m

1 stop

ORD12:26 pmChicago O'Hare Intl

$251

Find similar

Delta flights from Chicago to Portland, Maine

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

Delta

Nov 12

MDW6:00 amChicago Midway

5h 30m

1 stop

PWM12:30 pmPortland

Nov 15

PWM12:48 pmPortland

6h 20m

1 stop

MDW6:08 pmChicago Midway

$251

Find similar

Delta

Nov 12

ORD6:45 amChicago O'Hare Intl

4h 23m

1 stop

PWM12:08 pmPortland

Nov 15

PWM2:30 pmPortland

6h 59m

2 stops

ORD8:29 pmChicago O'Hare Intl

$256

Find similar

Delta

Nov 12

MDW1:14 pmChicago Midway

9h 40m

2 stops

PWM11:54 pmPortland

Nov 15

PWM2:30 pmPortland

10h 02m

2 stops

MDW11:32 pmChicago Midway

$261

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 10/31

7:58 am-11:28 am

Nonstop2h 30m

Portland

Fri 10/31

3:38 pm-9:10 pm

1 stop6h 32m

$238

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 11/12

1:45 pm-9:35 pm

1 stop6h 50m

Portland

Sat 11/15

5:37 pm-7:50 pm

Nonstop3h 13m

$241

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Wed 11/12

6:00 am-12:30 pm

1 stop5h 30m

Portland

Sat 11/15

12:48 pm-6:08 pm

1 stop6h 20m

$251

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 9/30

6:45 am-1:22 pm

1 stop5h 37m

Portland

Sat 10/4

7:09 am-6:23 pm

1 stop12h 14m

$253

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 11/12

6:45 am-12:08 pm

1 stop4h 23m

Portland

Sat 11/15

2:30 pm-8:29 pm

2 stops6h 59m

$256

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 10/1

1:35 pm-10:06 pm

1 stop7h 31m

Portland

Sat 10/4

7:09 am-6:23 pm

1 stop12h 14m

$263

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 10/1

6:10 pm-9:44 pm

Nonstop2h 34m

Portland

Tue 10/7

5:41 pm-11:30 pm

1 stop6h 49m

$265

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 11/4

10:53 am-2:12 pm

Nonstop2h 19m

Portland

Fri 11/7

4:54 pm-6:55 pm

Nonstop3h 01m

$269

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Fri 11/14

5:05 am-11:10 am

1 stop5h 05m

Portland

Tue 11/18

3:30 pm-9:05 pm

1 stop6h 35m

$275

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Sun 9/28

7:10 pm-10:25 pm

Nonstop2h 15m

Portland

Fri 10/3

2:40 pm-4:15 pm

Nonstop2h 35m

$279

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Showing 1-10 of 20 resultsSorted by cheapest first

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 typical price of a round-trip flight between Chicago and Portland, Maine?

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

The cheapest month to fly to Portland, Maine from Chicago is in March. Flight prices, which tend to average around $303, 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 February is also cheap. Prices for this month can be found on momondo for an average of $311.

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 $346. 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 $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 $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 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?

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 $408 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 $286 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 September 2025, prices for Chicago to Portland, Maine flights are approximately 5% 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	$188
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 $188. The best round-trip flight deal from Chicago to Portland, Maine found on momondo in the last 72 hours is $280.

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 September 2025, there are 4 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 Boeing 737-800 (20.89% of total bookings). The next most popular plane models are Embraer 175 (20.26%), Embraer 175 (Enhanced Winglets) (16.21%), and Boeing 737-700 (15.47%).
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 56% of all bookings. The subsequent popular airlines are American Airlines at 31%, Southwest at 10%, and JetBlue at 2%.

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
Delta	PriceFrom $163	Free Cancellation	Rating 7.9 7,957 reviews	Search Delta flights
United Airlines	PriceFrom $228	Free Cancellation	Rating 7.4 8,924 reviews	Search United Airlines flights
American Airlines	PriceFrom $232	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Southwest	PriceFrom $276	Free Cancellation	Rating 8.0 4,242 reviews	Search Southwest flights

Southwest Flights From Chicago to Portland, Maine
Across 5 Southwest flights from Chicago to Portland, Maine this week, the average price was $411, with the best Southwest deals starting from $276 round-trip. 4,242 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 $228 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around $385. United Airlines operates 19 flights to Portland, Maine from Chicago in an average week. Users have rated it 7.4/10 across 8,924 reviews.

North Conway

Boothbay Harbor

Jackson

Conway

Freeport

Lewiston

Bartlett

Gorham

Brunswick

Auburn

Intervale

Windham

Bath

Oxford

Georgetown

Tamworth

Falmouth

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 $96

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 10/20. 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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Filter for what you want

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American Airlines flights from Chicago to Portland, Maine

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

Delta flights from Chicago to Portland, Maine

Our best Delta 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 typical price of a round-trip flight between Chicago and 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?

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 September 2025, prices for Chicago to Portland, Maine flights are approximately 5% cheaper when compared to flights at the same time last year.

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

JetBlue, United Airlines, and American Airlines 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 10 per day as of September 2025. The most frequent departure time is 6:00PM, with 46% of daily flights leaving in the evening.

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

As of September 2025, there are 75 flights per week flying from Chicago to Portland, Maine. The most common day of the week flights depart is Mon, with 16% 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.