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$100+ 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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ORD
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from Portland to Illinois

Keep the following information in mind while searching for Portland to Illinois flight deals. Data was last updated August 14, 2025.

Round-trip from

$230
(American Airlines)

One-way from

$100
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$339

Good round-trip deal

$229 or less

Good one-way deal

$207 or less
From Portland to Illinois
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One-way flight from Portland to Illinois
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Highest demand for flights based on searches. 11% potential increase in price ($48 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Portland to Illinois.
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Price to beat on a one-way flight from Portland to Illinois.
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Find 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 August 14, 2025.

This American Airlines deal was found by Cheapflights users on 8/13. 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 8/3012:08 pmPWM - ORD
Nonstop3h 02mAmerican Airlines
Sun 8/318:05 amORD - PWM
Nonstop2h 33mAmerican Airlines
Deal found 8/13$230
This Delta deal was found by Cheapflights users on 8/13. 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 8/305:30 pmPWM - ORD
1 stop7h 26mDelta
Wed 9/36:00 amORD - PWM
1 stop16h 25mDelta
Deal found 8/13$231
This JetBlue deal was found by Cheapflights users on 8/14. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/302:19 pmPWM - ORD
1 stop9h 09mJetBlue
Fri 9/51:36 pmORD - PWM
1 stop7h 26mJetBlue
Deal found 8/14$233
This American Airlines deal was found by Cheapflights users on 8/14. 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 8/306:30 amPWM - ORD
Nonstop3h 02mAmerican Airlines
Thu 9/43:33 pmORD - PWM
1 stop7h 12mAmerican Airlines
Deal found 8/14$239
This Southwest deal was found by Cheapflights users on 8/13. 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 10/3110:25 amPWM - MDW
Nonstop2h 35mSouthwest
Sun 11/25:05 amMDW - PWM
1 stop5h 05mSouthwest
Deal found 8/13$239
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Tue 9/96:01 amPWM - ORD
Nonstop2h 56mAmerican Airlines
Wed 9/108:15 amORD - PWM
Nonstop2h 34mAmerican Airlines
Deal found 8/14$241
This Expedia deal was found by Cheapflights users on 8/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/47:09 amPWM - ORD
1 stop12h 14mJetBlue
Tue 10/71:36 pmORD - PWM
1 stop7h 25mJetBlue
Deal found 8/13$243
This American Airlines deal was found by Cheapflights users on 8/12. 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 9/176:15 amPWM - ORD
Nonstop2h 56mAmerican Airlines
Sun 9/218:15 amORD - PWM
Nonstop2h 34mAmerican Airlines
Deal found 8/12$245
This Delta deal was found by Cheapflights users on 8/13. 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 8/305:30 pmPWM - ORD
1 stop7h 26mDelta
Tue 9/211:05 amORD - PWM
1 stop5h 43mDelta
Deal found 8/13$249
This Southwest deal was found by Cheapflights users on 8/13. 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.
Tue 9/235:50 amPWM - MDW
1 stop6h 55mSouthwest
Tue 9/232:55 pmMDW - PWM
1 stop6h 30mSouthwest
Deal found 8/13$251
This Southwest deal was found by Cheapflights users on 8/13. 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.
Sat 8/304:50 pmPWM - MDW
Nonstop2h 35mSouthwest
Sun 8/315:55 pmMDW - PWM
Nonstop2h 20mSouthwest
Deal found 8/13$253
This Delta deal was found by Cheapflights users on 8/13. 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 8/276:00 amPWM - ORD
2 stops7h 45mDelta
Sun 8/315:45 amORD - PWM
1 stop5h 44mDelta
Deal found 8/13$254

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 August 14, 2025.
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 8/30

12:08 pm-2:10 pm

Nonstop3h 02m

Chicago O'Hare Intl

Sun 8/31

8:05 am-11:38 am

Nonstop2h 33m

$230

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 8/30

5:30 pm-11:56 pm

1 stop7h 26m

Chicago O'Hare Intl

Wed 9/3

6:00 am-11:25 pm

1 stop16h 25m

$231

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 9/23

6:14 am-8:05 am

Nonstop2h 51m

Chicago O'Hare Intl

Tue 9/23

1:55 pm-5:42 pm

Nonstop2h 47m

$231

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 8/30

1:34 pm-7:19 pm

1 stop6h 45m

Chicago O'Hare Intl

Mon 9/1

6:00 am-11:25 pm

1 stop16h 25m

$231

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 9/3

7:30 am-12:10 pm

1 stop5h 40m

Chicago O'Hare Intl

Fri 9/5

1:36 pm-10:02 pm

1 stop7h 26m

$233

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 8/30

2:19 pm-10:28 pm

1 stop9h 09m

Chicago O'Hare Intl

Fri 9/5

1:36 pm-10:02 pm

1 stop7h 26m

$233

PortlandChicago

PWM - MDW

PWMMDW

Portland

Fri 10/31

10:25 am-12:00 pm

Nonstop2h 35m

Chicago Midway

Sun 11/2

5:05 am-11:10 am

1 stop5h 05m

$239

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 10/31

6:29 am-8:23 am

Nonstop2h 54m

Chicago O'Hare Intl

Sun 11/2

5:05 am-10:49 am

1 stop4h 44m

$239

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 8/30

6:30 am-8:32 am

Nonstop3h 02m

Chicago O'Hare Intl

Thu 9/4

3:33 pm-11:45 pm

1 stop7h 12m

$239

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 9/30

12:21 pm-2:14 pm

Nonstop2h 53m

Chicago O'Hare Intl

Wed 10/1

7:00 am-12:29 pm

1 stop4h 29m

$241

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 57 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, August is the cheapest month in which you can book a flight from Portland, Maine to Illinois (average of $245). Flying from Portland, Maine to Illinois in March is currently the most expensive (average of $321). 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 August 14, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Portland, Maine to Illinois as you normally would.

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 August 14, 2025.

The most flights from PWM to USIL are scheduled on a Thursday (10 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 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 August 14, 2025.
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
4,244 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,916 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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.

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

    To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $100. Southwest flights start at $100 while deals on JetBlue start at $102 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: Envoy Air (97%), American Airlines (91%), SkyWest Airlines (80%).

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

    Looking at all options, your cheapest flight can be booked for $125. While the most popular route (Portland - Chicago O'Hare Intl) can be booked for $183 on average our data indicates $962 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, August is the cheapest month in which you can book a flight from Portland, Maine to Illinois (average of $245). Flying from Portland, Maine to Illinois in March is currently the most expensive (average of $321). 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

See prices for flight routes from nearby airports that may be better suited for you.
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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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$124Average$353FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$199Average$311FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$233Average$436FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$264Average$390FlexibilityNo cancel feeOn-time63%

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