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$113+ 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 1/28. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ORD
Jan 30 — Feb 61
Fri 1/30
Fri 2/6
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 December 31, 2025.

This United Airlines deal was found by Cheapflights users on 12/29. 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.
Wed 12/312:14 pmPWM - ORD
2 stops18h 36mUnited Airlines
Thu 1/110:35 amORD - PWM
Nonstop2h 39mUnited Airlines
Deal found 12/29$379
This United Airlines deal was found by Cheapflights users on 12/29. 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.
Wed 12/319:30 amPWM - ORD
Nonstop3h 14mUnited Airlines
Wed 12/312:00 pmORD - PWM
2 stops22h 39mUnited Airlines
Deal found 12/29$397
This Delta deal was found by Cheapflights users on 12/29. 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.
Tue 12/305:45 amPWM - ORD
1 stop6h 42mDelta
Tue 1/66:50 amORD - PWM
1 stop4h 18mDelta
Deal found 12/29$409
This United Airlines deal was found by Cheapflights users on 12/29. 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 12/302:55 pmPWM - ORD
1 stop7h 20mUnited Airlines
Tue 1/611:00 amORD - PWM
Nonstop2h 39mUnited Airlines
Deal found 12/29$424
This Southwest deal was found by Cheapflights users on 12/29. 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 12/305:30 amPWM - MDW
1 stop5h 55mSouthwest
Tue 1/66:50 amMDW - PWM
1 stop4h 20mSouthwest
Deal found 12/29$434
This United Airlines deal was found by Cheapflights users on 12/31. 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.
Wed 12/319:30 amPWM - ORD
Nonstop3h 14mUnited Airlines
Sun 1/46:21 pmORD - PWM
1 stop4h 38mUnited Airlines
Deal found 12/31$439
This Delta deal was found by Cheapflights users on 12/29. 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.
Tue 12/305:45 amPWM - ORD
1 stop6h 42mDelta
Wed 12/319:41 amORD - PWM
2 stops12h 02mDelta
Deal found 12/29$549
This Southwest deal was found by Cheapflights users on 12/31. 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.
Wed 12/313:30 pmPWM - MDW
1 stop6h 35mSouthwest
Sun 1/45:50 pmMDW - PWM
1 stop5h 15mSouthwest
Deal found 12/31$614
This American Airlines deal was found by Cheapflights users on 12/30. 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 12/317:17 amPWM - STL
1 stop9h 43mAmerican Airlines
Mon 1/55:00 amSTL - PWM
1 stop16h 51mAmerican Airlines
Deal found 12/30$834
This United Airlines deal was found by Cheapflights users on 12/30. 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.
Wed 12/312:55 pmPWM - STL
2 stops8h 48mUnited Airlines
Mon 1/51:05 pmSTL - PWM
2 stops9h 26mUnited Airlines
Deal found 12/30$895

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 December 31, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$209
(American Airlines)

One-way from

$113
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$455

Good round-trip deal

$398 or less

Good one-way deal

$263 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. 11% potential increase in price ($45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 31, 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 1/31

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

Tue 2/10

11:00 am-2:39 pm

Nonstop2h 39m

$209

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 1/31

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

Tue 2/3

11:00 am-2:39 pm

Nonstop2h 39m

$209

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 1/23

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

Tue 1/27

11:00 am-2:39 pm

Nonstop2h 39m

$209

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 5/23

6:00 am-7:57 am

Nonstop2h 57m

Chicago O'Hare Intl

Tue 5/26

6:00 pm-9:27 pm

Nonstop2h 27m

$209

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 1/23

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

Sun 1/25

11:00 am-2:39 pm

Nonstop2h 39m

$209

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 1/30

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

Mon 2/2

8:52 am-2:31 pm

1 stop4h 39m

$219

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 1/17

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

Mon 1/19

8:52 am-2:31 pm

1 stop4h 39m

$219

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 1/29

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

Thu 2/5

8:52 am-2:31 pm

1 stop4h 39m

$219

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 1/27

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

Tue 2/3

7:10 am-1:56 pm

1 stop5h 46m

$219

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 1/29

5:45 am-11:35 am

1 stop6h 50m

Chicago Midway

Thu 2/5

6:50 am-3:15 pm

1 stop7h 25m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/30

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, April is the cheapest month in which you can book a flight from Portland, Maine to Illinois (average of $89). 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 December 31, 2025.

It’s optimal to fly from Portland, Maine to Illinois in the evening. By choosing this option you can save up to 25% on the cost of your flight, compared to a flight in the afternoon.

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 December 31, 2025.

The most flights from PWM to USIL are scheduled on a Monday (4 on average). You will have fewer flight options on Wednesday, 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 December 31, 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
4,251 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

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
4,251 reviews
Southwest
8.0
Very good
4,251 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

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
8,013 reviews
Southwest
8.0
Very good
4,251 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

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
9,124 reviews
Southwest
8.0
Very good
4,251 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

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
11,075 reviews
Southwest
8.0
Very good
4,251 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

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 $209, United Airlines can have you in Illinois from Portland, Maine in 3h 12m. The distance between Portland, Maine and Illinois is about 897 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 $114 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: Republic Airways (85%), American Airlines (70%), United Airlines (66%).

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

    Looking at all options, your cheapest flight can be booked for $153. While the most popular route (Portland - Chicago O'Hare Intl) can be booked for $209 on average, our data indicates $504 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, April is the cheapest month in which you can book a flight from Portland, Maine to Illinois (average of $89). 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 December 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$124Average$352FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$208Average$306FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$231Average$435FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$246Average$397FlexibilityNo cancel feeOn-time63%

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