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

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

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

As of February 2026, there are 4 flights per day flying from Portland, Maine to Illinois. The most common time of day flights depart is 5:00AM, with 60% of flights taking off in the afternoon.

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

34 flights are operational weekly from Portland, Maine to Illinois as of February 2026. The most popular departure day for this route is Mon, with 15% of flights per week taking off on this day.

What airlines fly to Illinois?

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Illinois from Portland, Maine according to our data. American Airlines is the first choice among our users, with 41% of people opting to fly with this airline when traveling to Illinois. Keep in mind that there are 6 different airlines that fly to Illinois 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 Illinois?

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

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

There are 4 operators available for flights from Portland Airport to Illinois as of February 2026.

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

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Portland Airport to Illinois.

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

The required travel and health documents for your Illinois 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 Illinois. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$77 Cheap Flights from Portland to Illinois in 2026

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Find the cheapest flights from Portland, Maine to Illinois

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:03 am - 1:17 pm

PWM

ORD

8h 14m

2 stops

2:32 pm - 11:22 pm

ORD

PWM

7h 50m

1 stop

$209Delta

Wed, Apr 8 - Fri, Apr 10

4:48 pm - 8:17 pm

PWM

ORD

4h 29m

1 stop

2:32 pm - 11:22 pm

ORD

PWM

7h 50m

1 stop

$213Delta

Wed, Apr 8 - Fri, Apr 10

12:55 pm - 6:33 pm

PWM

MDW

6h 38m

1 stop

6:23 am - 1:10 pm

MDW

PWM

5h 47m

1 stop

$213Delta

Thu, May 7 - Sun, May 10

6:03 am - 12:29 pm

PWM

MDW

7h 26m

2 stops

1:10 pm - 11:22 pm

MDW

PWM

9h 12m

2 stops

$214Delta

Wed, Apr 8 - Fri, Apr 10

6:00 am - 11:04 am

PWM

ORD

6h 04m

1 stop

6:18 pm - 9:51 pm

ORD

PWM

2h 33mnonstop

$219United Airlines

Wed, Jul 1 - Wed, Jul 8

5:57 pm - 8:07 pm

PWM

ORD

3h 10mnonstop

4:04 pm - 11:55 pm

ORD

PWM

6h 51m

1 stop

$230American Airlines

Sat, Mar 28 - Tue, Mar 31

4:51 pm - 6:51 pm

PWM

ORD

3h 00mnonstop

6:18 pm - 9:51 pm

ORD

PWM

2h 33mnonstop

$237United Airlines

Wed, Jul 8 - Sat, Jul 11

6:10 am - 2:05 pm

PWM

MDW

8h 55m

2 stops

5:00 pm - 10:35 pm

MDW

PWM

4h 35m

1 stop

$240Southwest

Tue, May 5 - Tue, May 12

7:40 am - 9:15 am

PWM

MDW

2h 35mnonstop

5:30 pm - 10:55 pm

MDW

PWM

4h 25m

1 stop

$258Southwest

Fri, Jun 26 - Tue, Jun 30

7:07 am - 4:41 pm

PWM

STL

10h 34m

1 stop

7:05 am - 11:22 pm

STL

PWM

15h 17m

1 stop

$305American Airlines

Wed, May 13 - Sat, May 16

Delta flights from Portland, Maine to Illinois

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

Delta

Apr 8

PWM6:03 amPortland

8h 14m

2 stops

ORD1:17 pmChicago O'Hare Intl

Apr 10

ORD2:32 pmChicago O'Hare Intl

7h 50m

1 stop

PWM11:22 pmPortland

$209

Delta

Apr 8

PWM4:48 pmPortland

4h 29m

1 stop

ORD8:17 pmChicago O'Hare Intl

Apr 10

ORD2:32 pmChicago O'Hare Intl

7h 50m

1 stop

PWM11:22 pmPortland

$213

Delta

Apr 8

PWM6:03 amPortland

7h 26m

2 stops

MDW12:29 pmChicago Midway

Apr 10

MDW1:10 pmChicago Midway

9h 12m

2 stops

PWM11:22 pmPortland

$214

United Airlines flights from Portland, Maine to Illinois

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

United Airlines

May 2

PWM7:10 pmPortland

5h 34m

1 stop

ORD11:44 pmChicago O'Hare Intl

May 3

ORD7:15 amChicago O'Hare Intl

2h 38m

PWM10:53 amPortland

$219

United Airlines

Jul 8

PWM4:51 pmPortland

3h 00m

ORD6:51 pmChicago O'Hare Intl

Jul 11

ORD6:18 pmChicago O'Hare Intl

2h 33m

PWM9:51 pmPortland

$237

United Airlines

Jun 26

PWM6:25 pmPortland

3h 09m

ORD8:34 pmChicago O'Hare Intl

Jun 30

ORD10:55 amChicago O'Hare Intl

2h 31m

PWM2:26 pmPortland

$243

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 4/8

6:03 am-1:17 pm

2 stops8h 14m

Chicago O'Hare Intl

Fri 4/10

2:32 pm-11:22 pm

1 stop7h 50m

$209

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 4/8

4:48 pm-8:17 pm

1 stop4h 29m

Chicago O'Hare Intl

Fri 4/10

2:32 pm-11:22 pm

1 stop7h 50m

$213

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 5/7

12:55 pm-6:33 pm

1 stop6h 38m

Chicago Midway

Sun 5/10

6:23 am-1:10 pm

1 stop5h 47m

$213

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 4/8

6:03 am-12:29 pm

2 stops7h 26m

Chicago Midway

Fri 4/10

1:10 pm-11:22 pm

2 stops9h 12m

$214

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 7/1

6:00 am-11:04 am

1 stop6h 04m

Chicago O'Hare Intl

Wed 7/8

6:18 pm-9:51 pm

Nonstop2h 33m

$219

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 3/28

5:57 pm-8:07 pm

Nonstop3h 10m

Chicago O'Hare Intl

Tue 3/31

4:04 pm-11:55 pm

1 stop6h 51m

$230

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 7/8

4:51 pm-6:51 pm

Nonstop3h 00m

Chicago O'Hare Intl

Sat 7/11

6:18 pm-9:51 pm

Nonstop2h 33m

$237

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 5/5

6:10 am-2:05 pm

2 stops8h 55m

Chicago Midway

Tue 5/12

5:00 pm-10:35 pm

1 stop4h 35m

$240

PortlandChicago

PWM - MDW

PWMMDW

Portland

Fri 6/26

7:40 am-9:15 am

Nonstop2h 35m

Chicago Midway

Tue 6/30

5:30 pm-10:55 pm

1 stop4h 25m

$258

PortlandSt. Louis

PWM - STL

PWMSTL

Portland

Wed 5/13

7:07 am-4:41 pm

1 stop10h 34m

Lambert-St Louis

Sat 5/16

7:05 am-11:22 pm

1 stop15h 17m

$305

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 Illinois

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 Illinois?

The cheapest month to fly to Illinois from Portland, Maine is in April. Flight prices, which tend to average around $279, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of April, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $279.

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

The cheapest day to depart from Portland, Maine to Illinois is on a Thursday when prices can be found for as low as $430. Flights from Portland, Maine to Illinois on a Sunday will generally be more expensive and average around $570. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

Our most recent data shows that the best time of day to fly to Illinois is in the afternoon. Flights from Portland, Maine to Illinois during this time can be as low as $426. Flights in the morning are often more expensive with an average ticket price of $473.

What is the cheapest Portland to Illinois flight route?

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

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

You are more likely to see cheaper flights to Illinois from Portland, Maine when booking weeks ahead of your departure date. In general, you can expect to find flights to Illinois for around $352 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Illinois from Portland, Maine for as low as $233 on momondo.

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

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

Cheap Portland, Maine to Illinois flight deals and tips

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

Best Price Found	$178
Fastest flight time	2h 30m
Direct flights	Every day
Airports in Illinois	98 airports

The best one-way flight to Illinois from Portland, Maine in the past 72 hours is $178. The best round-trip flight deal from Portland, Maine to Illinois found on momondo in the last 72 hours is $348.

The fastest flight from Portland, Maine to Illinois takes 2h 30m

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

There are 98 airports in Illinois. From Portland, Maine there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).

Search flight deals

When did momondo last update prices for flights from Portland Airport to Illinois?
Prices for flights from Portland Airport to Illinois are updated daily.
How many operators does momondo search for flights from Portland Airport to Illinois?
There are 4 operators available for flights from Portland Airport to Illinois as of February 2026.
How old do you have to be to fly from Portland Airport to Illinois?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Portland Airport to Illinois.
What documentation or ID do you need to fly to Illinois?
The required travel and health documents for your Illinois 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 Illinois. 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 Portland, Maine to Illinois?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Portland, Maine to Illinois is Embraer 175 (Enhanced Winglets) (35.42% of total bookings). The next most popular plane models are Embraer 175 (26.43%), Boeing 737 MAX 8 (6.81%), and Airbus A220-300 (6.27%).

Best airlines flying from Portland, Maine to Illinois

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

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $114	Free Cancellation	Rating 7.9 8,242 reviews	Search Delta flights
American Airlines	PriceFrom $209	Free Cancellation	Rating 7.2 11,357 reviews	Search American Airlines flights
United Airlines	PriceFrom $223	Free Cancellation	Rating 7.4 9,349 reviews	Search United Airlines flights
Southwest	PriceFrom $246	Free Cancellation	Rating 8.0 4,301 reviews	Search Southwest flights

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Portland to Illinois for you.

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

Flights from Portland to Illinois 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 Portland to Illinois?

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

Price alerts on flights to Illinois from Portland are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Popular cities in Illinois

Flights to New Yorkfrom $56

Flights to Los Angelesfrom $54

Flights to Miamifrom $49

Flights to Orlandofrom $56

Flights to Chicagofrom $53

Flights to San Franciscofrom $50

Flights to Las Vegasfrom $53

Flights to Washington, D.C.from $56

Flights to Bostonfrom $75

Flights to Atlantafrom $49

Flights to Dallasfrom $54

Flights to Seattlefrom $48

Cheap flights from Portland, Maine to Illinois from $77

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 Illinois departing on 5/27. 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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Delta flights from Portland, Maine to Illinois

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

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

momondo Fare Finder

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

See travel insights to Illinois from

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

What is the cheapest month to fly to Illinois?

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

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

What is the cheapest Portland to Illinois flight route?

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

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

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

What airlines fly to Illinois?

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

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

Cheap Portland, Maine to Illinois flight deals and tips

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

Best Price Found

Fastest flight time

Direct flights

Airports in Illinois

Best airlines flying from Portland, Maine to Illinois

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

Why use momondo?

An easier way to manage your Illinois 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 Illinois

Popular cities in Illinois

Popular flights according to clicks in the last 7 days on momondo

Portland, Maine flight routes

According to popular flight searches on momondo this year

Illinois flight routes

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