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

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

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

40 flights are operational weekly from Portland, Maine to Illinois as of May 2026. The most popular departure day for this route is Fri, with 25% 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 42% 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.

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

As of May 2026, there are 5 flights per day flying from Portland, Maine to Illinois. The most common time of day flights depart is 6:00AM, with 37% of flights taking off in the afternoon.

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 May 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.

$99 Cheap Flights from Portland, Maine 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.

5:45 am - 11:50 am

PWM

MDW

7h 05m

2 stops

9:55 am - 9:00 pm

MDW

PWM

10h 05m

2 stops

$270Southwest

Wed, Sep 16 - Sat, Sep 19

6:00 am - 8:00 am

PWM

ORD

3h 00mnonstop

6:08 pm - 9:41 pm

ORD

PWM

2h 33mnonstop

$287United Airlines

Wed, Jul 1 - Sat, Jul 4

7:30 am - 9:05 am

PWM

MDW

2h 35mnonstop

7:40 am - 10:55 am

MDW

PWM

2h 15mnonstop

$287Southwest

Wed, Jul 1 - Sat, Jul 4

4:07 pm - 6:14 pm

PWM

ORD

3h 07mnonstop

7:59 pm - 11:47 pm

ORD

PWM

2h 48mnonstop

$292American Airlines

Sat, Sep 5 - Wed, Sep 9

7:40 am - 9:15 am

PWM

MDW

2h 35mnonstop

6:15 pm - 9:35 pm

MDW

PWM

2h 20mnonstop

$292Southwest

Fri, Jul 3 - Tue, Jul 7

12:16 pm - 2:22 pm

PWM

ORD

3h 06mnonstop

8:08 am - 11:45 am

ORD

PWM

2h 37mnonstop

$297American Airlines

Wed, Jul 15 - Wed, Jul 22

7:45 am - 9:20 am

PWM

MDW

2h 35mnonstop

6:50 pm - 10:05 pm

MDW

PWM

2h 15mnonstop

$297Southwest

Wed, Sep 2 - Wed, Sep 9

7:16 pm - 11:26 pm

PWM

ORD

5h 10m

1 stop

6:08 pm - 9:41 pm

ORD

PWM

2h 33mnonstop

$302United Airlines

Tue, Jun 23 - Tue, Jun 30

5:41 pm - 10:48 pm

PWM

ORD

6h 07m

1 stop

1:44 pm - 11:14 pm

ORD

PWM

8h 30m

1 stop

$312Delta

Fri, Jul 3 - Tue, Jul 7

12:40 pm - 6:31 pm

PWM

MDW

6h 51m

1 stop

1:26 pm - 11:00 pm

MDW

PWM

8h 34m

2 stops

$312Delta

Wed, Jul 1 - Fri, Jul 3

JetBlue flights from Portland, Maine to Illinois

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

JetBlue

Jul 24

PWM2:40 pmPortland

8h 18m

1 stop

ORD9:58 pmChicago O'Hare Intl

Jul 29

ORD6:00 amChicago O'Hare Intl

6h 45m

1 stop

PWM1:45 pmPortland

$347

JetBlue

Jul 4

PWM2:30 pmPortland

8h 00m

1 stop

ORD9:30 pmChicago O'Hare Intl

Jul 8

ORD6:00 amChicago O'Hare Intl

6h 45m

1 stop

PWM1:45 pmPortland

$353

JetBlue

Aug 14

PWM2:49 pmPortland

8h 06m

1 stop

ORD9:55 pmChicago O'Hare Intl

Aug 17

ORD6:00 amChicago O'Hare Intl

5h 21m

1 stop

PWM12:21 pmPortland

$357

American Airlines flights from Portland, Maine to Illinois

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

American Airlines

Sep 5

PWM4:07 pmPortland

3h 07m

ORD6:14 pmChicago O'Hare Intl

Sep 9

ORD7:59 pmChicago O'Hare Intl

2h 48m

PWM11:47 pmPortland

$292

American Airlines

Jul 15

PWM12:16 pmPortland

3h 06m

ORD2:22 pmChicago O'Hare Intl

Jul 22

ORD8:08 amChicago O'Hare Intl

2h 37m

PWM11:45 amPortland

$297

American Airlines

Jul 22

PWM12:51 pmPortland

5h 33m

1 stop

ORD5:24 pmChicago O'Hare Intl

Jul 28

ORD9:09 pmChicago O'Hare Intl

2h 34m

PWM12:43 amPortland

$307

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 9/16

5:45 am-11:50 am

2 stops7h 05m

Chicago Midway

Sat 9/19

9:55 am-9:00 pm

2 stops10h 05m

$270

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 7/1

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Sat 7/4

6:08 pm-9:41 pm

Nonstop2h 33m

$287

Quickest round-trip

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 7/1

7:30 am-9:05 am

Nonstop2h 35m

Chicago Midway

Sat 7/4

7:40 am-10:55 am

Nonstop2h 15m

$287

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 9/5

4:07 pm-6:14 pm

Nonstop3h 07m

Chicago O'Hare Intl

Wed 9/9

7:59 pm-11:47 pm

Nonstop2h 48m

$292

PortlandChicago

PWM - MDW

PWMMDW

Portland

Fri 7/3

7:40 am-9:15 am

Nonstop2h 35m

Chicago Midway

Tue 7/7

6:15 pm-9:35 pm

Nonstop2h 20m

$292

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 7/15

12:16 pm-2:22 pm

Nonstop3h 06m

Chicago O'Hare Intl

Wed 7/22

8:08 am-11:45 am

Nonstop2h 37m

$297

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 9/2

7:45 am-9:20 am

Nonstop2h 35m

Chicago Midway

Wed 9/9

6:50 pm-10:05 pm

Nonstop2h 15m

$297

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 6/23

7:16 pm-11:26 pm

1 stop5h 10m

Chicago O'Hare Intl

Tue 6/30

6:08 pm-9:41 pm

Nonstop2h 33m

$302

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 7/3

5:41 pm-10:48 pm

1 stop6h 07m

Chicago O'Hare Intl

Tue 7/7

1:44 pm-11:14 pm

1 stop8h 30m

$312

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 7/1

12:40 pm-6:31 pm

1 stop6h 51m

Chicago Midway

Fri 7/3

1:26 pm-11:00 pm

2 stops8h 34m

$312

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 September. Flight prices, which tend to average around $130, 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 September, then flying in November is also cheap. Prices for this month can be found on momondo for an average of $147.

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 Wednesday when prices can be found for as low as $432. Flights from Portland, Maine to Illinois on a Sunday will generally be more expensive and average around $612. 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 at noon. Flights from Portland, Maine to Illinois during this time can be as low as $393. Flights in the morning are often more expensive with an average ticket price of $481.

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 from Portland, Maine 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 $346 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 $254 on momondo.

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

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

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

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	$174
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 $174. The best round-trip flight deal from Portland, Maine to Illinois found on momondo in the last 72 hours is $378.

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

Frequently asked questions about flying from Portland, Maine to Illinois

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 May 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 (27.66% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (23.66%), Boeing 737 MAX 8 (20.93%), and Boeing 737-800 (7.92%).

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
American Airlines	PriceFrom $209	Free Cancellation	Rating 7.1 11,643 reviews	Search American Airlines flights
United Airlines	PriceFrom $239	Free Cancellation	Rating 7.4 9,762 reviews	Search United Airlines flights
Southwest	PriceFrom $267	Free Cancellation	Rating 8.0 4,264 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.

An easier way to manage your Illinois trip

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Popular cities in Illinois

Flights to New Yorkfrom $64

Flights to Los Angelesfrom $50

Flights to Orlandofrom $58

Flights to Miamifrom $111

Flights to Chicagofrom $67

Flights to San Franciscofrom $66

Flights to Las Vegasfrom $60

Flights to Washington, D.C.from $56

Flights to Bostonfrom $63

Flights to Atlantafrom $87

Flights to Fort Lauderdalefrom $58

Flights to Dallasfrom $56

Cheap flights from Portland, Maine to Illinois from $99

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 8/25. 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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JetBlue flights from Portland, Maine to Illinois

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

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

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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 from Portland, Maine to Illinois?

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

Can stopping save me money on Portland, Maine 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

Frequently asked questions about flying from Portland, Maine to 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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