Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Portland, Maine to Illinois from $128

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 5/16. 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

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Portland, Maine to Illinois

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
6:00 am - 8:00 am
PWM
-
ORD
3h 00mnonstop
United Airlines Logo
2:02 pm - 5:44 pm
ORD
-
PWM
2h 42mnonstop
$269United Airlines
Fri, May 22 - Mon, May 25
Southwest Logo
3:55 pm - 5:40 pm
PWM
-
MDW
2h 45mnonstop
Southwest Logo
7:55 pm - 11:10 pm
MDW
-
PWM
2h 15mnonstop
$269Southwest
Sat, Jun 6 - Sun, Jun 7
American Airlines Logo
6:01 pm - 8:14 pm
PWM
-
ORD
3h 13mnonstop
American Airlines Logo
8:39 pm - 12:17 am
ORD
-
PWM
2h 38mnonstop
$278American Airlines
Sat, May 16 - Tue, May 19
United Airlines Logo
6:00 am - 8:00 am
PWM
-
ORD
3h 00mnonstop
United Airlines Logo
3:53 pm - 11:51 pm
ORD
-
PWM
6h 58m
1 stop
$279United Airlines
Fri, May 22 - Sun, May 24
Southwest Logo
4:55 pm - 10:25 pm
PWM
-
MDW
6h 30m
1 stop
Southwest Logo
6:55 pm - 10:10 pm
MDW
-
PWM
2h 15mnonstop
$279Southwest
Sat, Jun 6 - Mon, Jun 8
Multiple Airlines Logo
5:01 pm - 2:39 pm
PWM
-
ORD
22h 38m
1 stop
Multiple Airlines Logo
3:55 pm - 4:16 pm
ORD
-
PWM
23h 21m
2 stops
$280Multiple Airlines
Sat, May 16 - Tue, May 19
Multiple Airlines Logo
5:01 pm - 2:39 pm
PWM
-
ORD
22h 38m
1 stop
Multiple Airlines Logo
1:50 pm - 7:16 pm
ORD
-
PWM
28h 26m
2 stops
$283Multiple Airlines
Sat, May 16 - Sat, May 23
American Airlines Logo
7:30 pm - 9:38 pm
PWM
-
ORD
3h 08mnonstop
American Airlines Logo
8:25 pm - 12:09 am
ORD
-
PWM
2h 44mnonstop
$287American Airlines
Wed, Jul 22 - Tue, Jul 28
Delta Logo
6:30 am - 12:17 pm
PWM
-
ORD
6h 47m
1 stop
Delta Logo
3:22 pm - 11:14 pm
ORD
-
PWM
6h 52m
1 stop
$289Delta
Wed, Jul 22 - Tue, Jul 28
Delta Logo
12:40 pm - 6:31 pm
PWM
-
MDW
6h 51m
1 stop
Delta Logo
9:17 am - 4:00 pm
MDW
-
PWM
5h 43m
1 stop
$289Delta
Fri, Jun 12 - Mon, Jun 15

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

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

Trusted and free

Trusted and free

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

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

American Airlines flights from Portland, Maine to Illinois

Our best American Airlines deals on Portland, Maine to Illinois flight tickets
American Airlines
May 16
PWM6:01 pmPortland
3h 13m
ORD8:14 pmChicago O'Hare Intl
May 19
ORD8:39 pmChicago O'Hare Intl
2h 38m
PWM12:17 amPortland
$278
American Airlines
Jul 22
PWM7:30 pmPortland
3h 08m
ORD9:38 pmChicago O'Hare Intl
Jul 28
ORD8:25 pmChicago O'Hare Intl
2h 44m
PWM12:09 amPortland
$287
American Airlines
Jun 6
PWM10:41 amPortland
6h 23m
1 stop
ORD4:04 pmChicago O'Hare Intl
Jun 7
ORD8:54 pmChicago O'Hare Intl
2h 43m
PWM12:37 amPortland
$288

Delta flights from Portland, Maine to Illinois

Our best Delta deals on Portland, Maine to Illinois flight tickets
Delta
Jun 12
PWM12:40 pmPortland
6h 51m
1 stop
MDW6:31 pmChicago Midway
Jun 15
MDW9:17 amChicago Midway
5h 43m
1 stop
PWM4:00 pmPortland
$289
Delta
May 9
PWM12:50 pmPortland
8h 34m
2 stops
ORD8:24 pmChicago O'Hare Intl
May 11
ORD6:31 pmChicago O'Hare Intl
5h 12m
1 stop
PWM12:43 amPortland
$294
Delta
May 9
PWM6:02 amPortland
11h 49m
2 stops
ORD4:51 pmChicago O'Hare Intl
May 16
ORD1:44 pmChicago O'Hare Intl
9h 59m
2 stops
PWM12:43 amPortland
$300

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 April 19, 2026.
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

Cheapest round-trip

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 5/22

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Mon 5/25

2:02 pm-5:44 pm

Nonstop2h 42m

$269
Quickest round-trip

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 6/6

3:55 pm-5:40 pm

Nonstop2h 45m

Chicago Midway

Sun 6/7

7:55 pm-11:10 pm

Nonstop2h 15m

$269

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 5/16

6:01 pm-8:14 pm

Nonstop3h 13m

Chicago O'Hare Intl

Tue 5/19

8:39 pm-12:17 am

Nonstop2h 38m

$278

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 5/22

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Sun 5/24

3:53 pm-11:51 pm

1 stop6h 58m

$279

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 6/6

4:55 pm-10:25 pm

1 stop6h 30m

Chicago Midway

Mon 6/8

6:55 pm-10:10 pm

Nonstop2h 15m

$279

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 5/16

5:01 pm-2:39 pm

1 stop22h 38m

Chicago O'Hare Intl

Tue 5/19

3:55 pm-4:16 pm

2 stops23h 21m

$280

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 5/16

5:01 pm-2:39 pm

1 stop22h 38m

Chicago O'Hare Intl

Sat 5/23

1:50 pm-7:16 pm

2 stops28h 26m

$283

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 7/22

7:30 pm-9:38 pm

Nonstop3h 08m

Chicago O'Hare Intl

Tue 7/28

8:25 pm-12:09 am

Nonstop2h 44m

$287

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 7/22

6:30 am-12:17 pm

1 stop6h 47m

Chicago O'Hare Intl

Tue 7/28

3:22 pm-11:14 pm

1 stop6h 52m

$289

PortlandChicago

PWM - MDW

PWMMDW

Portland

Fri 6/12

12:40 pm-6:31 pm

1 stop6h 51m

Chicago Midway

Mon 6/15

9:17 am-4:00 pm

1 stop5h 43m

$289

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 May. 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 May, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $281.

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 $422. Flights from Portland, Maine to Illinois on a Sunday will generally be more expensive and average around $573. 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 $415. Flights in the evening are often more expensive with an average ticket price of $486.

What is the cheapest Portland to Illinois flight route?

Fly from Portland to Chicago Midway 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 $344 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 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?

You could potentially save up to 15% on your flight if you consider stops on a Portland, Maine to Illinois flight.

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

$181

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 $181. The best round-trip flight deal from Portland, Maine to Illinois found on momondo in the last 72 hours is $367.
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?

  • 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
American AirlinesPriceFrom $209Free CancellationRating
7.1
11,621 reviews
Search American Airlines flights
United AirlinesPriceFrom $229Free CancellationRating
7.4
9,605 reviews
Search United Airlines flights
SouthwestPriceFrom $267Free CancellationRating
8.0
4,328 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

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 5/19
Tue 5/26
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Illinois

Popular cities in Illinois

Popular flights according to clicks in the last 7 days on momondo
Flights to New Yorkfrom $56
Flights to Los Angelesfrom $53
Flights to Orlandofrom $53
Flights to Miamifrom $50
Flights to Chicagofrom $67
Flights to San Franciscofrom $56
Flights to Las Vegasfrom $46
Flights to Washington, D.C.from $55
Flights to Bostonfrom $73
Flights to Atlantafrom $53
Flights to Dallasfrom $62
Flights to Fort Lauderdalefrom $47