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$99+ Cheap flights from Portland, ME (PWM) to Illinois

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/16. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ORD
Mar 20 — Mar 271
Fri 3/20
Fri 3/27
1 adult, Economy
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Cheap flight deals from Portland to Illinois

Cheapest flights from Portland to Illinois
Explore the most affordable flight options available from Portland to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 18, 2026.

This United Airlines deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/285:45 am
PWM
-
ORD
Nonstop3h 12m
United Airlines
Tue 3/3111:53 am
ORD
-
PWM
Nonstop2h 29m
United Airlines
Deal found 2/17$209
This Delta deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/24:43 pm
PWM
-
ORD
1 stop4h 57m
Delta
Wed 5/66:21 pm
ORD
-
PWM
1 stop5h 25m
Delta
Deal found 2/15$213
This Delta deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/212:46 pm
PWM
-
MDW
1 stop6h 12m
Delta
Wed 5/612:52 pm
MDW
-
PWM
2 stops10h 54m
Delta
Deal found 2/15$218
This United Airlines deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/97:36 pm
PWM
-
ORD
1 stop5h 07m
United Airlines
Sun 4/126:10 pm
ORD
-
PWM
Nonstop2h 30m
United Airlines
Deal found 2/18$219
This Southwest deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/51:00 pm
PWM
-
MDW
1 stop5h 50m
Southwest
Sun 6/77:55 pm
MDW
-
PWM
Nonstop2h 15m
Southwest
Deal found 2/18$219
This American Airlines deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/45:37 pm
PWM
-
ORD
Nonstop3h 13m
American Airlines
Sun 11/81:42 pm
ORD
-
PWM
Nonstop2h 25m
American Airlines
Deal found 2/17$229
This Delta deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/812:51 pm
PWM
-
MDW
1 stop6h 03m
Delta
Sun 4/129:35 am
MDW
-
PWM
1 stop5h 31m
Delta
Deal found 2/18$229
This American Airlines deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/286:17 am
PWM
-
ORD
Nonstop3h 17m
American Airlines
Tue 3/316:40 am
ORD
-
PWM
1 stop4h 34m
American Airlines
Deal found 2/18$230
This United Airlines deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/124:45 pm
PWM
-
ORD
Nonstop2h 58m
United Airlines
Wed 5/135:56 pm
ORD
-
PWM
Nonstop2h 23m
United Airlines
Deal found 2/16$231
This Delta deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:50 pm
PWM
-
ORD
1 stop6h 05m
Delta
Tue 7/281:15 pm
ORD
-
PWM
2 stops9h 44m
Delta
Deal found 2/17$234
This Southwest deal was found by Cheapflights users on 2/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/232:50 pm
PWM
-
MDW
2 stops6h 20m
Southwest
Wed 3/256:30 am
MDW
-
PWM
1 stop4h 25m
Southwest
Deal found 2/18$234
This American Airlines deal was found by Cheapflights users on 2/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:15 am
PWM
-
ORD
Nonstop3h 01m
American Airlines
Sat 8/2911:40 am
ORD
-
PWM
1 stop6h 37m
American Airlines
Deal found 2/17$239

Find flight deals from Portland to Illinois

Keep the following information in mind while searching for Portland to Illinois flight deals. Data was last updated February 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$209
(United Airlines)

One-way from

$99
(Delta)

Popular in

December

Cheapest in

April

Average price

$382

Good round-trip deal

$371 or less

Good one-way deal

$178 or less
Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Chicago (CHI) flights.
Search Deals
From Portland to Illinois
Search Deals
One-way flight from Portland to Illinois
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($39 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals
Price to beat on a round-trip flight from Portland to Illinois.
Search Deals
Price to beat on a one-way flight from Portland to Illinois.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland 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, Cheapflights users made 2,558,603 searches. Data last updated February 18, 2026.
Use the filters below to find and compare flights from Portland to Illinois that are best for you.

Fly from

Portland

Fly to

Illinois

Route

Depart

Return

Price

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 5/23

6:25 pm-8:34 pm

Nonstop3h 09m

Chicago O'Hare Intl

Mon 5/25

6:18 pm-9:51 pm

Nonstop2h 33m

$209

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 7/2

4:58 pm-6:58 pm

Nonstop3h 00m

Chicago O'Hare Intl

Sun 7/5

6:25 pm-9:58 pm

Nonstop2h 33m

$209

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 5/2

12:46 pm-11:59 pm

2 stops12h 13m

Chicago O'Hare Intl

Wed 5/6

6:21 pm-12:46 am

1 stop5h 25m

$218

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 7/29

3:00 pm-7:22 pm

1 stop5h 22m

Chicago O'Hare Intl

Sat 8/1

12:10 pm-11:59 pm

2 stops10h 49m

$218

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 4/9

7:36 pm-11:43 pm

1 stop5h 07m

Chicago O'Hare Intl

Mon 4/13

6:10 pm-9:40 pm

Nonstop2h 30m

$219

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 7/2

7:15 pm-11:21 pm

1 stop5h 06m

Chicago O'Hare Intl

Mon 7/20

6:25 pm-9:58 pm

Nonstop2h 33m

$219

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 7/11

5:20 am-9:36 am

1 stop5h 16m

Chicago O'Hare Intl

Mon 7/13

6:25 pm-9:58 pm

Nonstop2h 33m

$219

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 5/2

12:46 pm-10:28 pm

2 stops10h 42m

Chicago Midway

Wed 5/6

12:52 pm-12:46 am

2 stops10h 54m

$223

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 5/14

12:52 pm-6:13 pm

1 stop6h 21m

Chicago O'Hare Intl

Mon 5/18

7:00 am-11:57 am

1 stop3h 57m

$229

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 7/22

6:50 pm-11:55 pm

1 stop6h 05m

Chicago O'Hare Intl

Tue 7/28

11:10 am-6:01 pm

1 stop5h 51m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/14

Showing 1-10 of 51 results
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Best time to book a flight from Portland to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Portland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Portland to Illinois

What is the cheapest month to book a flight from Portland, Maine to Illinois?

Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Illinois (average of $91). Flying from Portland, Maine to Illinois in January is currently the most expensive (average of $123). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from PWM to IL?

Find hourly flight availability from Portland to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 18, 2026.

It’s optimal to fly from Portland, Maine to Illinois in the morning. By choosing this option you can save up to 41% on the cost of your flight, compared to a flight in the evening.

Weekly flight availability from Portland, Maine to Illinois

Explore weekly flight availability from Portland to Illinois. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated February 18, 2026.

The most flights from PWM to USIL are scheduled on a Monday (5 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Illinois. Reviews last updated February 18, 2026.
Read through reviews of airlines operating flights from Portland to Illinois, such as Southwest, Delta, and United Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,212 reviews
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,321 reviews
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,313 reviews
Southwest
8.0
Very good
4,295 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Portland to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Portland to Illinois?

    Portland (PWM) is the airport you will fly out of if you book a flight from Portland to Illinois. It is only a 2.9 mi journey to Portland (PWM) from Portland’s city center.

  • How long is the flight from Portland, Maine to Illinois?

    For as low as $248, United Airlines can have you in Illinois from Portland, Maine in 2h 35m. The distance between Portland, Maine and Illinois is about 892 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Portland, Maine to Illinois one-way?

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $95. American Airlines flights start at $104 while deals on Delta start at $105 one-way.

  • What are the most popular routes from Portland, Maine to Illinois?

    The most popular route from Portland, Maine to Illinois is Portland - Chicago O'Hare Intl. You may also consider Portland - Chicago Midway or Portland - Lambert-St Louis.

  • What are the most reliable airlines from Portland, Maine to Illinois?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Portland, Maine to Illinois on time: American Airlines (100%), Envoy Air (100%), Republic Airways (97%).

  • What are the cheapest flights from Portland, Maine to Illinois?

    Looking at all options, your cheapest flight can be booked for $143. While the most popular route (Portland - Chicago O'Hare Intl) can be booked for $209 on average, our data indicates $877 when flying from Portland, Maine to Illinois.

  • Can I find deals for flights from Portland to Illinois that include hotel bookings?

    Yes. In addition to deals on Portland to Illinois flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Illinois?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Illinois.

  • Can I find deals for business class flights from Portland to Illinois?

    Yes. Cheapflights offers flight deals from Portland to Illinois by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Portland, Maine to Illinois?

    Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Illinois (average of $91). Flying from Portland, Maine to Illinois in January is currently the most expensive (average of $123). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Portland to Illinois

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Top 4 airlines flying from Portland to Illinois

Discover the top 4 airlines that operate flights from Portland to Illinois. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$114Average$351FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$209Average$307FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$226Average$419FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$246Average$397FlexibilityNo cancel feeOn-time63%

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