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Cheap flights from Portland, Maine to Illinois 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 Illinois departing on 3/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Portland, Maine to Illinois

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
5:30 pm - 7:20 pm
PWM
-
ORD
2h 50mnonstop
American Airlines Logo
6:45 am - 12:00 pm
ORD
-
PWM
4h 15m1 stop
$264American Airlines
Fri, May 8 - Mon, May 11
American Airlines Logo
12:09 pm - 5:52 pm
PWM
-
ORD
6h 43m1 stop
American Airlines Logo
1:30 pm - 10:25 pm
ORD
-
PWM
7h 55m1 stop
$269American Airlines
Thu, Apr 9 - Mon, Apr 13
Southwest Logo
5:45 am - 11:35 am
PWM
-
MDW
6h 50m1 stop
Southwest Logo
6:50 am - 2:55 pm
MDW
-
PWM
7h 05m1 stop
$269Southwest
Tue, Jan 27 - Thu, Jan 29
Southwest Logo
1:00 pm - 5:35 pm
PWM
-
MDW
5h 35m1 stop
Southwest Logo
6:50 am - 2:55 pm
MDW
-
PWM
7h 05m1 stop
$274Southwest
Sun, Feb 1 - Sun, Feb 8
Multiple Airlines Logo
11:29 am - 9:27 pm
PWM
-
ORD
10h 58m2 stops
Multiple Airlines Logo
12:44 pm - 9:07 am
ORD
-
PWM
19h 23m1 stop
$276Multiple Airlines
Mon, Feb 2 - Sun, Feb 8
United Airlines Logo
4:10 pm - 6:18 pm
PWM
-
ORD
3h 08mnonstop
United Airlines Logo
3:35 pm - 11:27 pm
ORD
-
PWM
6h 52m1 stop
$277United Airlines
Thu, Jan 8 - Tue, Jan 13
United Airlines Logo
4:10 pm - 6:18 pm
PWM
-
ORD
3h 08mnonstop
United Airlines Logo
11:00 am - 2:39 pm
ORD
-
PWM
2h 39mnonstop
$278United Airlines
Thu, Jan 15 - Tue, Jan 20
Delta Logo
6:00 am - 1:08 pm
PWM
-
ORD
8h 08m2 stops
Delta Logo
5:20 pm - 11:22 pm
ORD
-
PWM
5h 02m1 stop
$284Delta
Fri, Jan 9 - Fri, Jan 9
Delta Logo
12:20 pm - 5:34 pm
PWM
-
MDW
6h 14m1 stop
Delta Logo
9:32 am - 10:27 pm
MDW
-
PWM
11h 55m2 stops
$284Delta
Mon, Jan 5 - Fri, Jan 9
Multiple Airlines Logo
6:18 pm - 11:45 am
PWM
-
MDW
18h 27m2 stops
Multiple Airlines Logo
1:00 pm - 9:07 am
MDW
-
PWM
19h 07m1 stop
$310Multiple Airlines
Sat, Jan 31 - Sun, Feb 8

American Airlines flights from Portland, Maine to Illinois

Our best American Airlines deals on Portland, Maine to Illinois flight tickets
American Airlines
May 8
PWM5:30 pmPortland
2h 50m
ORD7:20 pmChicago O'Hare Intl
May 11
ORD6:45 amChicago O'Hare Intl
4h 15m
1 stop
PWM12:00 pmPortland
$264
Find similar
American Airlines
Apr 9
PWM12:09 pmPortland
6h 43m
1 stop
ORD5:52 pmChicago O'Hare Intl
Apr 13
ORD1:30 pmChicago O'Hare Intl
7h 55m
1 stop
PWM10:25 pmPortland
$269
Find similar
American Airlines
Jan 9
PWM7:00 amPortland
7h 22m
1 stop
ORD1:22 pmChicago O'Hare Intl
Jan 16
ORD3:48 pmChicago O'Hare Intl
6h 55m
1 stop
PWM11:43 pmPortland
$294
Find similar

United Airlines flights from Portland, Maine to Illinois

Our best United Airlines deals on Portland, Maine to Illinois flight tickets
United Airlines
Jan 8
PWM4:10 pmPortland
3h 08m
ORD6:18 pmChicago O'Hare Intl
Jan 13
ORD3:35 pmChicago O'Hare Intl
6h 52m
1 stop
PWM11:27 pmPortland
$277
Find similar
United Airlines
Jan 15
PWM4:10 pmPortland
3h 08m
ORD6:18 pmChicago O'Hare Intl
Jan 20
ORD11:00 amChicago O'Hare Intl
2h 39m
PWM2:39 pmPortland
$278
Find similar
United Airlines
Jan 31
PWM4:10 pmPortland
3h 08m
ORD6:18 pmChicago O'Hare Intl
Feb 9
ORD11:00 amChicago O'Hare Intl
2h 39m
PWM2:39 pmPortland
$279
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Portland, Maine to Illinois that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated December 15, 2025.
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

Fri 5/8

5:30 pm-7:20 pm

Nonstop2h 50m

Chicago O'Hare Intl

Mon 5/11

6:45 am-12:00 pm

1 stop4h 15m

$264

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 4/9

12:09 pm-5:52 pm

1 stop6h 43m

Chicago O'Hare Intl

Mon 4/13

1:30 pm-10:25 pm

1 stop7h 55m

$269

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 1/27

5:45 am-11:35 am

1 stop6h 50m

Chicago Midway

Thu 1/29

6:50 am-2:55 pm

1 stop7h 05m

$269

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sun 2/1

1:00 pm-5:35 pm

1 stop5h 35m

Chicago Midway

Sun 2/8

6:50 am-2:55 pm

1 stop7h 05m

$274

PortlandChicago

PWM - ORD

PWMORD

Portland

Mon 2/2

11:29 am-9:27 pm

2 stops10h 58m

Chicago O'Hare Intl

Sun 2/8

12:44 pm-9:07 am

1 stop19h 23m

$276

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 1/8

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

Tue 1/13

3:35 pm-11:27 pm

1 stop6h 52m

$277

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 1/15

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

Tue 1/20

11:00 am-2:39 pm

Nonstop2h 39m

$278

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 1/9

6:00 am-1:08 pm

2 stops8h 08m

Chicago O'Hare Intl

Fri 1/9

5:20 pm-11:22 pm

1 stop5h 02m

$284

PortlandChicago

PWM - MDW

PWMMDW

Portland

Mon 1/5

12:20 pm-5:34 pm

1 stop6h 14m

Chicago Midway

Fri 1/9

9:32 am-10:27 pm

2 stops11h 55m

$284

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 1/31

6:18 pm-11:45 am

2 stops18h 27m

Chicago Midway

Sun 2/8

1:00 pm-9:07 am

1 stop19h 07m

$310

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Illinois from

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

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 $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 September, then flying in May 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 Illinois?

The cheapest day to depart from Portland, Maine to Illinois is on a Thursday when prices can be found for as low as $425. Flights from Portland, Maine to Illinois on a Sunday will generally be more expensive and average around $596. 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 $432. Flights in the morning are often more expensive with an average ticket price of $480.

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 $366 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 $234 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.

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

$298

Fastest flight time

2h 35m

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 $298. The best round-trip flight deal from Portland, Maine to Illinois found on momondo in the last 72 hours is $400.
The fastest flight from Portland, Maine to Illinois takes 2h 35m
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?

  • 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?

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
DeltaPriceFrom $124Free CancellationRating
7.9
8,007 reviews
Search Delta flights
American AirlinesPriceFrom $209Free CancellationRating
7.2
11,052 reviews
Search American Airlines flights
United AirlinesPriceFrom $234Free CancellationRating
7.4
9,092 reviews
Search United Airlines flights
SouthwestPriceFrom $246Free CancellationRating
7.9
4,250 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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