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

Chicago (ORD) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

What airlines fly to Chicago?

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Chicago from Portland, Maine according to our data. American Airlines is the first choice among our users, with 40% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

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

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

As of February 2026, 12 flights take off from Portland, Maine and land in Chicago each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.

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

1 flights are operational daily from Portland, Maine to Chicago as of February 2026. The most popular departure time for this route is 4:00PM, with 100% of flights per day taking off in the afternoon.

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

Flights connecting via Philadelphia (PHL) have the shortest average one-way travel time: 5h 02m.

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

Flights via Chicago (ORD) offer the lowest average round-trip price of $253.

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

Philadelphia (PHL) has the shortest average layover time for this route: 0h 53m.

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

Prices for flights from Portland Airport to Chicago are updated daily.

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

As of February 2026, there are 4 operators available to choose from for flights from Portland Airport to Chicago.

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

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents required for your trip to Chicago 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 Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$113 Cheap Flights from Portland to Chicago in 2026

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Find the cheapest flights from Portland, Maine to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:13 pm - 8:23 pm

PWM

ORD

3h 10mnonstop

6:10 pm - 9:40 pm

ORD

PWM

2h 30mnonstop

$209United Airlines

Fri, Apr 3 - Mon, Apr 6

9:40 am - 11:36 am

PWM

ORD

2h 56mnonstop

4:25 pm - 11:59 pm

ORD

PWM

6h 34m

1 stop

$219United Airlines

Sat, May 16 - Tue, May 19

4:50 pm - 10:45 pm

PWM

MDW

6h 55m

1 stop

9:50 am - 2:55 pm

MDW

PWM

4h 05m

1 stop

$229Southwest

Thu, Feb 26 - Tue, Mar 3

12:52 pm - 4:25 pm

PWM

ORD

4h 33m

1 stop

7:00 am - 11:57 am

ORD

PWM

3h 57m

1 stop

$229Delta

Fri, May 22 - Mon, May 25

1:18 pm - 7:22 pm

PWM

ORD

7h 04m

1 stop

7:49 pm - 11:27 pm

ORD

PWM

2h 38mnonstop

$230American Airlines

Tue, Apr 7 - Sun, Apr 12

6:00 am - 8:00 am

PWM

ORD

3h 00mnonstop

6:25 pm - 9:58 pm

ORD

PWM

2h 33mnonstop

$232United Airlines

Thu, Jun 18 - Sun, Jun 21

6:50 pm - 11:55 pm

PWM

ORD

6h 05m

1 stop

1:15 pm - 11:59 pm

ORD

PWM

9h 44m

2 stops

$234Delta

Wed, Jul 22 - Tue, Jul 28

5:31 am - 11:59 am

PWM

MDW

7h 28m

1 stop

9:50 am - 11:20 pm

MDW

PWM

12h 30m

2 stops

$234Delta

Thu, Feb 26 - Mon, Mar 2

5:51 pm - 8:04 pm

PWM

ORD

3h 13mnonstop

5:45 pm - 11:22 pm

ORD

PWM

4h 37m

1 stop

$239American Airlines

Fri, Apr 10 - Mon, Apr 13

5:45 am - 11:35 am

PWM

MDW

6h 50m

1 stop

9:50 am - 2:55 pm

MDW

PWM

4h 05m

1 stop

$268Southwest

Wed, Feb 25 - Tue, Mar 3

United Airlines flights from Portland, Maine to Chicago

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

United Airlines

Apr 3

PWM6:13 pmPortland

3h 10m

ORD8:23 pmChicago O'Hare Intl

Apr 6

ORD6:10 pmChicago O'Hare Intl

2h 30m

PWM9:40 pmPortland

$209

United Airlines

May 16

PWM9:40 amPortland

2h 56m

ORD11:36 amChicago O'Hare Intl

May 19

ORD4:25 pmChicago O'Hare Intl

6h 34m

1 stop

PWM11:59 pmPortland

$219

United Airlines

Jun 18

PWM6:00 amPortland

3h 00m

ORD8:00 amChicago O'Hare Intl

Jun 21

ORD6:25 pmChicago O'Hare Intl

2h 33m

PWM9:58 pmPortland

$232

American Airlines flights from Portland, Maine to Chicago

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

American Airlines

Apr 7

PWM1:18 pmPortland

7h 04m

1 stop

ORD7:22 pmChicago O'Hare Intl

Apr 12

ORD7:49 pmChicago O'Hare Intl

2h 38m

PWM11:27 pmPortland

$230

American Airlines

Apr 10

PWM5:51 pmPortland

3h 13m

ORD8:04 pmChicago O'Hare Intl

Apr 13

ORD5:45 pmChicago O'Hare Intl

4h 37m

1 stop

PWM11:22 pmPortland

$239

American Airlines

Apr 21

PWM5:51 pmPortland

3h 13m

ORD8:04 pmChicago O'Hare Intl

Apr 27

ORD7:49 pmChicago O'Hare Intl

2h 38m

PWM11:27 pmPortland

$254

Fly from

Fly to

Route

Depart

Return

Price

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 4/3

6:13 pm-8:23 pm

Nonstop3h 10m

Chicago O'Hare Intl

Mon 4/6

6:10 pm-9:40 pm

Nonstop2h 30m

$209

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 5/16

9:40 am-11:36 am

Nonstop2h 56m

Chicago O'Hare Intl

Tue 5/19

4:25 pm-11:59 pm

1 stop6h 34m

$219

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 2/26

4:50 pm-10:45 pm

1 stop6h 55m

Chicago Midway

Tue 3/3

9:50 am-2:55 pm

1 stop4h 05m

$229

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 5/22

12:52 pm-4:25 pm

1 stop4h 33m

Chicago O'Hare Intl

Mon 5/25

7:00 am-11:57 am

1 stop3h 57m

$229

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 4/7

1:18 pm-7:22 pm

1 stop7h 04m

Chicago O'Hare Intl

Sun 4/12

7:49 pm-11:27 pm

Nonstop2h 38m

$230

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 6/18

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Sun 6/21

6:25 pm-9:58 pm

Nonstop2h 33m

$232

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 7/22

6:50 pm-11:55 pm

1 stop6h 05m

Chicago O'Hare Intl

Tue 7/28

1:15 pm-11:59 pm

2 stops9h 44m

$234

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 2/26

5:31 am-11:59 am

1 stop7h 28m

Chicago Midway

Mon 3/2

9:50 am-11:20 pm

2 stops12h 30m

$234

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 4/10

5:51 pm-8:04 pm

Nonstop3h 13m

Chicago O'Hare Intl

Mon 4/13

5:45 pm-11:22 pm

1 stop4h 37m

$239

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 2/25

5:45 am-11:35 am

1 stop6h 50m

Chicago Midway

Tue 3/3

9:50 am-2:55 pm

1 stop4h 05m

$268

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

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 Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Portland, Maine, with most prices found around $279. If you’re not able to fly to Chicago in September, then April is your next best option. Flight prices from Portland, Maine to Chicago during April average around $305.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $423. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Portland, Maine to Chicago for around $587.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Portland, Maine to Chicago during this time can be as low as $432. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $469.

What is the cheapest Portland to Chicago flight route?

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

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Portland, Maine when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $356 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Portland, Maine for as low as $233 on momondo.

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

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

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

As of February 2026, prices for Portland, Maine to Chicago flights are approximately 72% more expensive when compared to flights at the same time last year.

When to book flights from Portland, Maine to Chicago

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

Estimated round-trip price

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

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

Best Price Found	$186
Fastest flight time	2h 35m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Portland, Maine in the past 72 hours is $186. The best round-trip flight deal from Portland, Maine to Chicago found on momondo in the last 72 hours is $370.

The fastest flight from Portland, Maine to Chicago takes 2h 35m

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

There are 3 airports in Chicago. From Portland, Maine there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).

Search flight deals

How far is Portland to Chicago by plane?
There are 887.4 mi between Portland and Chicago. Flights usually cover this in 2h 35m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Portland Airport to Chicago?
Prices for flights from Portland Airport to Chicago are updated daily.
How many operators does momondo search for flights from Portland Airport to Chicago?
As of February 2026, there are 4 operators available to choose from for flights from Portland Airport to Chicago.
How old do you have to be to fly from Portland Airport to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago 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 Chicago. 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 Portland, Maine to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Portland, Maine to Chicago is Embraer 175 (Enhanced Winglets) (34.55% of total bookings). The next most popular plane models are Embraer 175 (18.94%), Boeing 737 MAX 8 (7.64%), and Airbus A220-300 (6.98%).
What is the most popular airline from Portland, Maine to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Portland, Maine to Chicago is United Airlines (60% of total bookings). The next most popular airlines are American Airlines (36%) and Southwest (4%).

Best airlines flying from Portland, Maine to Chicago

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

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $114	Free Cancellation	Rating 7.9 8,172 reviews	Search Delta flights
American Airlines	PriceFrom $209	Free Cancellation	Rating 7.2 11,249 reviews	Search American Airlines flights
United Airlines	PriceFrom $227	Free Cancellation	Rating 7.4 9,254 reviews	Search United Airlines flights
Southwest	PriceFrom $246	Free Cancellation	Rating 8.0 4,280 reviews	Search Southwest flights

United Airlines Flights From Portland, Maine to Chicago
United Airlines is one of the most popular airlines flying from Portland, Maine to Chicago, operating 6 flights/week on average for this route. A good United Airlines flight deal for Portland, Maine to Chicago starts from $227 round-trip, up to an average price of $372. Our users have rated United Airlines at 7.4/10.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Munster

Crown Point

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Portland to Chicago. momondo saves you time and could save you money on your trip.

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

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

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

Once you have performed a search for Portland to Chicago 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 Portland to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Portland to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Cheap flights from Portland, Maine to Chicago from $115

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Portland, Maine to Chicago departing on 4/7. 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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United Airlines flights from Portland, Maine to Chicago

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

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

What is the cheapest month to fly to Chicago?

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Portland, Maine to Chicago during this time can be as low as $432. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $469.

What is the cheapest Portland to Chicago flight route?

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

How far in advance should I book a flight to Chicago?

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

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

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

As of February 2026, prices for Portland, Maine to Chicago flights are approximately 72% more expensive when compared to flights at the same time last year.

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

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

What airlines fly to Chicago?

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

Chicago (ORD) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

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

Flights via Chicago (ORD) offer the lowest average round-trip price of $253.

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

Flights connecting via Philadelphia (PHL) have the shortest average one-way travel time: 5h 02m.

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

Philadelphia (PHL) has the shortest average layover time for this route: 0h 53m.

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

1 flights are operational daily from Portland, Maine to Chicago as of February 2026. The most popular departure time for this route is 4:00PM, with 100% of flights per day taking off in the afternoon.

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

As of February 2026, 12 flights take off from Portland, Maine and land in Chicago each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.

When to book flights from Portland, Maine to Chicago

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

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

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

How far is Portland to Chicago by plane?

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

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

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

What documentation or ID do you need to fly to Chicago?

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

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

Best airlines flying from Portland, Maine to Chicago

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

United Airlines Flights From Portland, Maine to Chicago

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago 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

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago

Fly your favorite airline to Chicago