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 Illinois according to our data. American Airlines is the first choice among our users, with 39% 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 Illinois to Portland, Maine on average per week?

As of November 2025, 41 flights take off from Illinois and land in Portland, Maine each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.

How long does it take to fly to Portland, Maine?

The flight from Illinois to Portland, Maine depends on which airports you’re departing and arriving from and whether or not you have a layover. If you fly from Chicago (a popular airport in Illinois) to Boston (the most popular airport in Portland, Maine), then the flight time is 2h 15m on average. If you fly from Peoria (another popular airport in Illinois) to Boston, then the average flight time is 5h 10m.

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

As of November 2025, there are 5 flights per day flying from Illinois to Portland, Maine. The most common time of day flights depart is 6:00PM, with 50% of flights taking off in the evening.

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

Delta, Southwest, and United Airlines are the most popular carriers operating from Illinois to Portland

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

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

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

As of November 2025, there are 4 operators available to choose from for flights from Illinois to Portland Airport.

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

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 Illinois to Portland Airport.

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

The required travel and health documents for your Portland Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Portland Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$84 Cheap Flights from Illinois to Portland in 2025/26

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Illinois to Portland

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

3:30 pm - 9:06 amSTL-PWM

16h 36m1 stop

9:46 am - 10:33 pmPWM-STL

13h 47m1 stop

$270Multiple Airlines

Find Deal

Thu, Dec 4 - Mon, Dec 8

9:45 am - 5:16 pmSTL-PWM

6h 31m1 stop

1:13 pm - 5:31 pmPWM-STL

5h 18m1 stop

$273Delta

Find Deal

Wed, Jan 21 - Sat, Jan 24

4:58 pm - 11:45 pmSTL-PWM

5h 47m1 stop

12:46 pm - 5:23 pmPWM-STL

5h 37m1 stop

$274American Airlines

Find Deal

Mon, Jan 5 - Mon, Jan 12

9:59 am - 11:22 pmSTL-PWM

12h 23m2 stops

1:13 pm - 5:31 pmPWM-STL

5h 18m1 stop

$278Delta

Find Deal

Wed, Jan 21 - Sat, Jan 24

12:09 pm - 10:36 amORD-PWM

21h 27m1 stop

11:29 am - 9:39 pmPWM-ORD

11h 10m2 stops

$281Multiple Airlines

Find Deal

Tue, Dec 9 - Mon, Jan 12

10:10 am - 10:15 pmMDW-PWM

11h 05m2 stops

5:45 am - 1:55 pmPWM-MDW

9h 10m2 stops

$284Southwest

Find Deal

Thu, Jan 8 - Mon, Jan 12

11:00 am - 2:39 pmORD-PWM

2h 39mnonstop

8:40 am - 4:06 pmPWM-ORD

8h 26m1 stop

$289United Airlines

Find Deal

Thu, Jan 8 - Mon, Jan 12

10:50 am - 2:22 pmORD-PWM

2h 32mnonstop

4:10 pm - 6:18 pmPWM-ORD

3h 08mnonstop

$299United Airlines

Find Deal

Wed, Dec 10 - Sat, Jan 10

7:05 am - 3:15 pmMDW-PWM

7h 10m1 stop

5:10 am - 11:25 amPWM-MDW

7h 15m1 stop

$304Southwest

Find Deal

Sun, Jan 11 - Sat, Jan 17

11:07 am - 10:59 pmMLI-PWM

10h 52m2 stops

12:43 pm - 11:08 pmPWM-MLI

11h 25m2 stops

$349American Airlines

Find Deal

Sat, Feb 14 - Wed, Feb 18

Southwest flights from Illinois to Portland, Maine

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

Southwest

Jan 8

MDW10:10 amChicago Midway

11h 05m

2 stops

PWM10:15 pmPortland

Jan 12

PWM5:45 amPortland

9h 10m

2 stops

MDW1:55 pmChicago Midway

$284

Find similar

Southwest

Jan 11

MDW7:05 amChicago Midway

7h 10m

1 stop

PWM3:15 pmPortland

Jan 17

PWM5:10 amPortland

7h 15m

1 stop

MDW11:25 amChicago Midway

$304

Find similar

Southwest

Jan 11

MDW5:25 amChicago Midway

8h 50m

2 stops

PWM3:15 pmPortland

Jan 17

PWM5:10 amPortland

7h 15m

1 stop

MDW11:25 amChicago Midway

$309

Find similar

American Airlines flights from Illinois to Portland, Maine

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

American Airlines

Jan 5

STL4:58 pmLambert-St Louis

5h 47m

1 stop

PWM11:45 pmPortland

Jan 12

PWM12:46 pmPortland

5h 37m

1 stop

STL5:23 pmLambert-St Louis

$274

Find similar

American Airlines

Nov 27

ORD5:00 amChicago O'Hare Intl

8h 08m

1 stop

PWM2:08 pmPortland

Dec 1

PWM6:37 pmPortland

5h 19m

1 stop

ORD10:56 pmChicago O'Hare Intl

$324

Find similar

American Airlines

Dec 31

ORD4:05 pmChicago O'Hare Intl

5h 46m

1 stop

PWM10:51 pmPortland

Jan 6

PWM7:00 amPortland

7h 22m

1 stop

ORD1:22 pmChicago O'Hare Intl

$331

Find similar

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

St. LouisPortland

STL - PWM

STLPWM

Lambert-St Louis

Thu 12/4

3:30 pm-9:06 am

1 stop16h 36m

Portland

Mon 12/8

9:46 am-10:33 pm

1 stop13h 47m

$270

St. LouisPortland

STL - PWM

STLPWM

Lambert-St Louis

Wed 1/21

9:45 am-5:16 pm

1 stop6h 31m

Portland

Sat 1/24

1:13 pm-5:31 pm

1 stop5h 18m

$273

St. LouisPortland

STL - PWM

STLPWM

Lambert-St Louis

Mon 1/5

4:58 pm-11:45 pm

1 stop5h 47m

Portland

Mon 1/12

12:46 pm-5:23 pm

1 stop5h 37m

$274

St. LouisPortland

STL - PWM

STLPWM

Lambert-St Louis

Wed 1/21

9:59 am-11:22 pm

2 stops12h 23m

Portland

Sat 1/24

1:13 pm-5:31 pm

1 stop5h 18m

$278

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 12/9

12:09 pm-10:36 am

1 stop21h 27m

Portland

Mon 1/12

11:29 am-9:39 pm

2 stops11h 10m

$281

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Thu 1/8

10:10 am-10:15 pm

2 stops11h 05m

Portland

Mon 1/12

5:45 am-1:55 pm

2 stops9h 10m

$284

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 1/8

11:00 am-2:39 pm

Nonstop2h 39m

Portland

Mon 1/12

8:40 am-4:06 pm

1 stop8h 26m

$289

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 12/10

10:50 am-2:22 pm

Nonstop2h 32m

Portland

Sat 1/10

4:10 pm-6:18 pm

Nonstop3h 08m

$299

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Sun 1/11

7:05 am-3:15 pm

1 stop7h 10m

Portland

Sat 1/17

5:10 am-11:25 am

1 stop7h 15m

$304

MolinePortland

MLI - PWM

MLIPWM

Moline Quad-City

Sat 2/14

11:07 am-10:59 pm

2 stops10h 52m

Portland

Wed 2/18

12:43 pm-11:08 pm

2 stops11h 25m

$349

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 Illinois 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

Other information

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

The cheapest month to fly to Portland, Maine from Illinois is in February. Flight prices, which tend to average around $282, 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 $309.

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 Illinois is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $337. 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 Illinois because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $397.

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 Illinois 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 $376. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Illinois to Portland flight route?

Fly from Chicago O'Hare Intl to Portland for the best Illinois - 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 Illinois when booking weeks ahead of your departure date. In general, you can expect to find flights to Portland, Maine for around $386 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Portland, Maine from Illinois for as low as $286 on momondo.

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

There are 4 cabin classes available to choose from on Illinois 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 Illinois to Portland, Maine flights?

You could potentially save up to 28% on your flight if you consider stops on a Illinois to Portland, Maine flight.

Cheap Illinois to Portland, Maine flight deals and tips

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

Best Price Found	$231
Fastest flight time	2h 19m
Direct flights	Every day
Airports in Portland, Maine	1 airport

The best one-way flight to Portland, Maine from Illinois in the past 72 hours is $231. The best round-trip flight deal from Illinois to Portland, Maine found on momondo in the last 72 hours is $391.

The fastest flight from Illinois to Portland, Maine takes 2h 19m

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

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

Search flight deals

When did momondo last update prices for flights from Illinois to Portland Airport?
Prices for flights from Illinois to Portland Airport are updated daily.
How many operators does momondo search for flights from Illinois to Portland Airport?
As of November 2025, there are 4 operators available to choose from for flights from Illinois to Portland Airport.
How old do you have to be to fly from Illinois to Portland Airport?
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 Illinois to Portland Airport.
What documentation or ID do you need to fly to Portland Airport?
The required travel and health documents for your Portland Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Portland Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Illinois to Portland, Maine?
Based on momondo bookings for flights between Illinois and Portland, Maine, the leading plane model is Boeing 737-800, making up 21.52% of the total bookings. Other popular models include Embraer 175 with 19.04%, Embraer 175 (Enhanced Winglets) with 17.28%, and Canadair (Bombardier) Regional Jet 700 with 15.76%.

Best airlines flying from Illinois to Portland, Maine

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

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $163	Free Cancellation	Rating 7.9 8,000 reviews	Search Delta flights
United Airlines	PriceFrom $226	Free Cancellation	Rating 7.4 9,036 reviews	Search United Airlines flights
American Airlines	PriceFrom $232	Free Cancellation	Rating 7.2 11,047 reviews	Search American Airlines flights
Southwest	PriceFrom $313	Free Cancellation	Rating 8.0 4,253 reviews	Search Southwest flights

North Conway

Boothbay Harbor

Jackson

Conway

Lewiston

Freeport

Brunswick

Bartlett

Auburn

Gorham

Windham

Intervale

Oxford

Bath

Georgetown

Falmouth

Tamworth

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Illinois to Portland. Millions of users trust and use momondo every year so you are in good hands.

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

Flights from Illinois to Portland with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

momondo helps you find the best flight between Illinois 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 Illinois to Portland right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Portland, momondo offers a useful price alert feature which will track prices for flights to Portland from Illinois and alert you when they 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.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Tue 12/23

Tue 12/30

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Cheap flights from Illinois to Portland from $113

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to Portland departing on 1/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Illinois to Portland

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Southwest flights from Illinois to Portland, Maine

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

American Airlines flights from Illinois to Portland, Maine

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

momondo Fare Finder

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

See travel insights to Portland from

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

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

How far in advance should I book a flight to Portland, Maine?

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

There are 4 cabin classes available to choose from on Illinois 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 Illinois to Portland, Maine flights?

You could potentially save up to 28% on your flight if you consider stops on a Illinois to Portland, Maine flight.

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

Delta, Southwest, and United Airlines are the most popular carriers operating from Illinois to Portland

What airlines fly to Portland, Maine?

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

As of November 2025, there are 5 flights per day flying from Illinois to Portland, Maine. The most common time of day flights depart is 6:00PM, with 50% of flights taking off in the evening.

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

As of November 2025, 41 flights take off from Illinois and land in Portland, Maine each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.

How long does it take to fly to Portland, Maine?

Cheap Illinois to Portland, Maine flight deals and tips

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

Best Price Found

Fastest flight time

Direct flights

Airports in Portland, Maine

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

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

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

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

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

Best airlines flying from Illinois to Portland, Maine

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

Traveling to a place near Portland?

Why use momondo?

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

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

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

I’m not ready to book a flight from Illinois 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

Airports servicing Maine