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

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

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

3 flights are operational daily from Portland, Maine to Chicago as of November 2025. The most popular departure time for this route is 9:00AM, with 59% of flights per day taking off in the afternoon.

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

As of November 2025, 25 flights take off from Portland, Maine and land in Chicago each week. The most common flight departure day for this route is Mon, with 20% of weekly flights taking off on this day.

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 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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 November 2025, 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.

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

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

Prices are currently low for flights on this route. Typical prices usually range from $359 to $580. The lowest price recently found on this route was $245.

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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.

6:00 am - 4:42 pmPWM-ORD

11h 42m2 stops

6:45 am - 12:13 pmORD-PWM

4h 28m1 stop

$245Delta

Find Deal

Wed, Dec 3 - Sun, Dec 7

4:10 pm - 6:24 pmPWM-ORD

3h 14mnonstop

3:53 pm - 11:22 pmORD-PWM

6h 29m1 stop

$247United Airlines

Find Deal

Thu, Dec 25 - Wed, Dec 31

4:57 pm - 6:52 pmPWM-ORD

2h 55mnonstop

10:53 am - 2:12 pmORD-PWM

2h 19mnonstop

$249United Airlines

Find Deal

Sat, Nov 15 - Sun, Nov 16

6:36 pm - 10:56 pmPWM-ORD

5h 20m1 stop

3:44 pm - 9:37 pmORD-PWM

4h 53m1 stop

$251American Airlines

Find Deal

Tue, Dec 2 - Tue, Dec 9

6:00 am - 12:05 pmPWM-ORD

7h 05m1 stop

3:53 pm - 11:22 pmORD-PWM

6h 29m1 stop

$257United Airlines

Find Deal

Thu, Dec 25 - Wed, Dec 31

5:30 am - 10:10 amPWM-MDW

5h 40m1 stop

12:55 pm - 10:15 pmMDW-PWM

8h 20m1 stop

$274Southwest

Find Deal

Wed, Nov 19 - Wed, Nov 19

5:30 am - 1:00 pmPWM-MDW

8h 30m2 stops

2:30 pm - 10:15 pmMDW-PWM

6h 45m2 stops

$279Southwest

Find Deal

Wed, Nov 19 - Wed, Nov 19

7:02 am - 2:14 pmPWM-ORD

8h 12m1 stop

3:44 pm - 9:35 pmORD-PWM

4h 51m1 stop

$290American Airlines

Find Deal

Thu, Nov 27 - Tue, Dec 2

9:46 am - 10:10 pmPWM-MDW

13h 24m1 stop

1:56 pm - 5:38 pmMDW-PWM

26h 42m2 stops

$320Multiple Airlines

Find Deal

Fri, Nov 14 - Tue, Nov 18

11:21 am - 11:06 pmPWM-ORD

12h 45m2 stops

5:25 am - 9:06 amORD-PWM

26h 41m1 stop

$332Multiple Airlines

Find Deal

Sat, Nov 15 - Sun, Nov 16

Delta flights from Portland, Maine to Chicago

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

Delta

Dec 3

PWM6:00 amPortland

11h 42m

2 stops

ORD4:42 pmChicago O'Hare Intl

Dec 7

ORD6:45 amChicago O'Hare Intl

4h 28m

1 stop

PWM12:13 pmPortland

$245

Find similar

Delta

Nov 15

PWM12:48 pmPortland

6h 20m

1 stop

MDW6:08 pmChicago Midway

Nov 16

MDW6:00 amChicago Midway

5h 30m

1 stop

PWM12:30 pmPortland

$269

Find similar

Delta

Nov 17

PWM4:40 pmPortland

5h 04m

1 stop

ORD8:44 pmChicago O'Hare Intl

Nov 20

ORD5:23 amChicago O'Hare Intl

9h 44m

2 stops

PWM4:07 pmPortland

$274

Find similar

United Airlines flights from Portland, Maine to Chicago

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

United Airlines

Dec 25

PWM4:10 pmPortland

3h 14m

ORD6:24 pmChicago O'Hare Intl

Dec 31

ORD3:53 pmChicago O'Hare Intl

6h 29m

1 stop

PWM11:22 pmPortland

$247

Find similar

United Airlines

Nov 15

PWM4:57 pmPortland

2h 55m

ORD6:52 pmChicago O'Hare Intl

Nov 16

ORD10:53 amChicago O'Hare Intl

2h 19m

PWM2:12 pmPortland

$249

Find similar

United Airlines

Dec 25

PWM6:00 amPortland

7h 05m

1 stop

ORD12:05 pmChicago O'Hare Intl

Dec 31

ORD3:53 pmChicago O'Hare Intl

6h 29m

1 stop

PWM11:22 pmPortland

$257

Find similar

Fly from

Fly to

Route

Depart

Return

Price

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 12/3

6:00 am-4:42 pm

2 stops11h 42m

Chicago O'Hare Intl

Sun 12/7

6:45 am-12:13 pm

1 stop4h 28m

$245

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 12/25

4:10 pm-6:24 pm

Nonstop3h 14m

Chicago O'Hare Intl

Wed 12/31

3:53 pm-11:22 pm

1 stop6h 29m

$247

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 11/15

4:57 pm-6:52 pm

Nonstop2h 55m

Chicago O'Hare Intl

Sun 11/16

10:53 am-2:12 pm

Nonstop2h 19m

$249

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 12/2

6:36 pm-10:56 pm

1 stop5h 20m

Chicago O'Hare Intl

Tue 12/9

3:44 pm-9:37 pm

1 stop4h 53m

$251

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 12/25

6:00 am-12:05 pm

1 stop7h 05m

Chicago O'Hare Intl

Wed 12/31

3:53 pm-11:22 pm

1 stop6h 29m

$257

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 11/19

5:30 am-10:10 am

1 stop5h 40m

Chicago Midway

Wed 11/19

12:55 pm-10:15 pm

1 stop8h 20m

$274

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 11/19

5:30 am-1:00 pm

2 stops8h 30m

Chicago Midway

Wed 11/19

2:30 pm-10:15 pm

2 stops6h 45m

$279

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 11/27

7:02 am-2:14 pm

1 stop8h 12m

Chicago O'Hare Intl

Tue 12/2

3:44 pm-9:35 pm

1 stop4h 51m

$290

PortlandChicago

PWM - MDW

PWMMDW

Portland

Fri 11/14

9:46 am-10:10 pm

1 stop13h 24m

Chicago Midway

Tue 11/18

1:56 pm-5:38 pm

2 stops26h 42m

$320

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 11/15

11:21 am-11:06 pm

2 stops12h 45m

Chicago O'Hare Intl

Sun 11/16

5:25 am-9:06 am

1 stop26h 41m

$332

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Other information

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

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 May is your next best option. Flight prices from Portland, Maine to Chicago during May average around $304.

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 $430. 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 $620.

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 $487.

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 $372 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 $228 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.

Can stopping save me money on Portland, Maine to Chicago flights?

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

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

As of November 2025, prices for Portland, Maine to Chicago flights are approximately 13% cheaper 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	$189
Fastest flight time	2h 55m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from Portland, Maine in the past 72 hours is $189. The best round-trip flight deal from Portland, Maine to Chicago found on momondo in the last 72 hours is $337.

The fastest flight from Portland, Maine to Chicago takes 2h 55m

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

There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

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 55m, 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 November 2025, 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) (19.88% of total bookings). The next most popular plane models are Canadair (Bombardier) Regional Jet 700 (16.58%), Embraer 175 (15.36%), and Boeing 737 MAX 8 (12.15%).
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 (62% of total bookings). The next most popular airlines are American Airlines (30%), Southwest (5%), and Delta (3%).

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 $124	Free Cancellation	Rating 7.9 8,002 reviews	Search Delta flights
American Airlines	PriceFrom $203	Free Cancellation	Rating 7.2 11,038 reviews	Search American Airlines flights
United Airlines	PriceFrom $229	Free Cancellation	Rating 7.4 8,997 reviews	Search United Airlines flights
Southwest	PriceFrom $246	Free Cancellation	Rating 8.0 4,238 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 7 flights/week on average for this route. A good United Airlines flight deal for Portland, Maine to Chicago starts from $229 round-trip, up to an average price of $376. Our users have rated United Airlines at 7.4/10.
American Airlines Flights From Portland, Maine to Chicago
American Airlines (7.2/10 from 11,038 reviews) operates around 7 flights from Portland, Maine to Chicago in any given week. The average American Airlines airfare for this route is around $304, with deals from around $203 rare but found on momondo. Referenced prices are for round-trip Portland, Maine to Chicago flight searches in the last 72 hours.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

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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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Popular cities in the United States

Flights to New Yorkfrom $49

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Flights to Las Vegasfrom $49

Flights to San Franciscofrom $54

Flights to Washington, D.C.from $54

Flights to Bostonfrom $40

Flights to Atlantafrom $40

Flights to Dallasfrom $49

Flights to Seattlefrom $68

Flights to Denverfrom $47

Cheap flights from Portland, Maine to Chicago 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 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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Big names and deals

Filter for what you want

Filter for what you want

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Find the cheapest flights from Portland, Maine to Chicago

Cheap round-trip flights

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Cheap last minute flights

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Delta flights from Portland, Maine to Chicago

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

United Airlines flights from Portland, Maine to Chicago

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

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

See travel insights to Chicago from

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

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

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 May is your next best option. Flight prices from Portland, Maine to Chicago during May average around $304.

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 $487.

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.

Can stopping save me money on Portland, Maine to Chicago flights?

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

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

As of November 2025, prices for Portland, Maine to Chicago flights are approximately 13% cheaper when compared to flights at the same time last year.

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

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

What airlines fly to Chicago?

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

3 flights are operational daily from Portland, Maine to Chicago as of November 2025. The most popular departure time for this route is 9:00AM, with 59% of flights per day taking off in the afternoon.

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

As of November 2025, 25 flights take off from Portland, Maine and land in Chicago each week. The most common flight departure day for this route is Mon, with 20% 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

American 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