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.

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.

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

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

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

As of October 2025, there are 25 flights per week flying from Chicago to Portland, Maine. The most common day of the week flights depart is Thu, with 40% of flights taking off on this day.

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 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 3 per day as of October 2025. The most frequent departure time is 6:00PM, with 51% of daily flights leaving in the evening.

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.

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 October 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.

$101 Cheap Flights from Chicago to Portland in 2025/26

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Cheap round-trip flights

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1:15 pm - 11:19 pmMDW-PWM

9h 04m2 stops

6:00 am - 11:52 amPWM-MDW

6h 52m1 stop

$244Delta

Find Deal

mar., nov. 11 - mar., nov. 18

7:00 am - 1:50 pmORD-PWM

5h 50m1 stop

4:53 pm - 8:29 pmPWM-ORD

4h 36m1 stop

$249Delta

Find Deal

jue., nov. 13 - sáb., nov. 15

5:05 am - 11:10 amMDW-PWM

5h 05m1 stop

3:00 pm - 8:40 pmPWM-MDW

6h 40m1 stop

$263Southwest

Find Deal

vie., nov. 21 - lun., nov. 24

12:00 pm - 5:48 pmORD-PWM

4h 48m1 stop

7:22 pm - 11:43 pmPWM-ORD

5h 21m1 stop

$268United Airlines

Find Deal

mar., nov. 18 - sáb., nov. 22

5:05 am - 11:10 amMDW-PWM

5h 05m1 stop

3:00 pm - 8:30 pmPWM-MDW

6h 30m2 stops

$268Southwest

Find Deal

vie., nov. 21 - lun., nov. 24

12:09 pm - 9:06 amORD-PWM

19h 57m1 stop

11:29 am - 12:01 amPWM-ORD

37h 32m2 stops

$272Multiple Airlines

Find Deal

dom., dic. 7 - vie., ene. 9

4:40 pm - 11:09 pmORD-PWM

5h 29m1 stop

4:10 pm - 6:18 pmPWM-ORD

3h 08mnonstop

$285United Airlines

Find Deal

vie., dic. 12 - vie., ene. 9

8:00 am - 10:36 amORD-PWM

25h 36m1 stop

11:16 am - 11:06 pmPWM-ORD

12h 50m1 stop

$288Multiple Airlines

Find Deal

mar., nov. 11 - sáb., nov. 15

1:40 pm - 5:05 pmORD-PWM

2h 25mnonstop

5:37 pm - 7:50 pmPWM-ORD

3h 13mnonstop

$328American Airlines

Find Deal

vie., nov. 21 - dom., nov. 23

5:17 pm - 11:42 pmORD-PWM

5h 25m1 stop

6:00 am - 10:50 amPWM-ORD

5h 50m1 stop

$344American Airlines

Find Deal

lun., dic. 22 - jue., ene. 1

Delta flights from Chicago to Portland, Maine

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

Delta

Nov 11

MDW1:15 pmChicago Midway

9h 04m

2 stops

PWM11:19 pmPortland

Nov 18

PWM6:00 amPortland

6h 52m

1 stop

MDW11:52 amChicago Midway

$244

Find similar

Delta

Nov 13

ORD7:00 amChicago O'Hare Intl

5h 50m

1 stop

PWM1:50 pmPortland

Nov 15

PWM4:53 pmPortland

4h 36m

1 stop

ORD8:29 pmChicago O'Hare Intl

$249

Find similar

Delta

Nov 12

ORD6:00 amChicago O'Hare Intl

9h 07m

2 stops

PWM4:07 pmPortland

Nov 15

PWM1:25 pmPortland

6h 26m

1 stop

ORD6:51 pmChicago O'Hare Intl

$254

Find similar

Southwest flights from Chicago to Portland, Maine

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

Southwest

Nov 21

MDW5:05 amChicago Midway

5h 05m

1 stop

PWM11:10 amPortland

Nov 24

PWM3:00 pmPortland

6h 40m

1 stop

MDW8:40 pmChicago Midway

$263

Find similar

Southwest

Nov 21

MDW5:05 amChicago Midway

5h 05m

1 stop

PWM11:10 amPortland

Nov 24

PWM3:00 pmPortland

6h 30m

2 stops

MDW8:30 pmChicago Midway

$268

Find similar

Southwest

Nov 10

MDW5:15 pmChicago Midway

6h 05m

1 stop

PWM12:20 amPortland

Nov 15

PWM12:40 pmPortland

6h 50m

1 stop

MDW6:30 pmChicago Midway

$299

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

mar. 11/11

1:15 pm-11:19 pm

2 stops9h 04m

Portland

mar. 11/18

6:00 am-11:52 am

1 stop6h 52m

$244

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

jue. 11/13

7:00 am-1:50 pm

1 stop5h 50m

Portland

sáb. 11/15

4:53 pm-8:29 pm

1 stop4h 36m

$249

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

vie. 11/21

5:05 am-11:10 am

1 stop5h 05m

Portland

lun. 11/24

3:00 pm-8:40 pm

1 stop6h 40m

$263

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

mar. 11/18

12:00 pm-5:48 pm

1 stop4h 48m

Portland

sáb. 11/22

7:22 pm-11:43 pm

1 stop5h 21m

$268

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

vie. 11/21

5:05 am-11:10 am

1 stop5h 05m

Portland

lun. 11/24

3:00 pm-8:30 pm

2 stops6h 30m

$268

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

dom. 12/7

12:09 pm-9:06 am

1 stop19h 57m

Portland

vie. 1/9

11:29 am-12:01 am

2 stops37h 32m

$272

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

vie. 12/12

4:40 pm-11:09 pm

1 stop5h 29m

Portland

vie. 1/9

4:10 pm-6:18 pm

Nonstop3h 08m

$285

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

mar. 11/11

8:00 am-10:36 am

1 stop25h 36m

Portland

sáb. 11/15

11:16 am-11:06 pm

1 stop12h 50m

$288

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

vie. 11/21

1:40 pm-5:05 pm

Nonstop2h 25m

Portland

dom. 11/23

5:37 pm-7:50 pm

Nonstop3h 13m

$328

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

lun. 12/22

5:17 pm-11:42 pm

1 stop5h 25m

Portland

jue. 1/1

6:00 am-10:50 am

1 stop5h 50m

$344

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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 $309, 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 $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 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 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 $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 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?

You could potentially save up to 28% 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 October 2025, prices for Chicago to Portland, Maine flights are approximately 5% more expensive 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	$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 in the past 72 hours is $230. The best round-trip flight deal from Chicago to Portland, Maine found on momondo in the last 72 hours is $391.

The fastest flight from Chicago to Portland, Maine takes 2h 17m

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 19m.
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 October 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 (21.31% of total bookings). The next most popular plane models are Embraer 175 (19.37%), Embraer 175 (Enhanced Winglets) (17.00%), and Canadair (Bombardier) Regional Jet 700 (15.21%).
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 57% of all bookings. The subsequent popular airlines are American Airlines at 31%, Southwest at 9%, and JetBlue at 1%.

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 7,998 reviews	Search Delta flights
United Airlines	PriceFrom $226	Free Cancellation	Rating 7.4 8,998 reviews	Search United Airlines flights
American Airlines	PriceFrom $232	Free Cancellation	Rating 7.2 11,035 reviews	Search American Airlines flights
Southwest	PriceFrom $313	Free Cancellation	Rating 8.0 4,243 reviews	Search Southwest flights

Southwest Flights From Chicago to Portland, Maine
Across 1 Southwest flight from Chicago to Portland, Maine this week, the average price was $411, with the best Southwest deals starting from $313 round-trip. 4,243 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 $226 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around $381. United Airlines operates 7 flights to Portland, Maine from Chicago in an average week. Users have rated it 7.4/10 across 8,998 reviews.

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?

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.

Start using Trips

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Cheap flights from Chicago to Portland from $101

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 4/1. 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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Delta flights from Chicago to Portland, Maine

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

Southwest flights from Chicago to Portland, Maine

Our best Southwest 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?

You could potentially save up to 28% 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 October 2025, prices for Chicago to Portland, Maine flights are approximately 5% more expensive when compared to flights at the same time last year.

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

JetBlue, Delta, 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 3 per day as of October 2025. The most frequent departure time is 6:00PM, with 51% of daily flights leaving in the evening.

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

As of October 2025, there are 25 flights per week flying from Chicago to Portland, Maine. The most common day of the week flights depart is Thu, with 40% 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.