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$90+ 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 7/2. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ORD
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$219
(American Airlines)

One-way from

$90
(United Airlines)

Popular in

November

Cheapest in

September

Average price

$366

Good round-trip deal

$314 or less

Good one-way deal

$173 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. 12% potential increase in price ($52 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/11. 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.
Thu 6/266:00 amPWM - ORD
Nonstop2h 57mAmerican Airlines
Mon 6/307:09 pmORD - PWM
Nonstop2h 38mAmerican Airlines
Deal found 6/11$219
This United Airlines deal was found by Cheapflights users on 6/10. 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 7/110:05 amPWM - ORD
1 stop7h 47mUnited Airlines
Wed 7/96:30 pmORD - PWM
Nonstop2h 31mUnited Airlines
Deal found 6/10$229
This JetBlue deal was found by Cheapflights users on 6/11. 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 8/22:19 pmPWM - ORD
1 stop9h 09mJetBlue
Tue 8/56:10 amORD - PWM
1 stop6h 13mJetBlue
Deal found 6/11$233
This Delta deal was found by Cheapflights users on 6/10. 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.
Mon 6/306:56 pmPWM - ORD
1 stop6h 03mDelta
Sat 7/127:00 amORD - PWM
1 stop16h 57mDelta
Deal found 6/10$235
This Southwest deal was found by Cheapflights users on 6/10. 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 7/15:30 amPWM - ORD
1 stop7h 20mSouthwest
Fri 7/111:50 pmORD - PWM
1 stop9h 15mSouthwest
Deal found 6/10$244
This Delta deal was found by Cheapflights users on 6/11. 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 7/212:49 pmPWM - MDW
1 stop6h 52mDelta
Wed 7/99:25 amMDW - PWM
1 stop5h 46mDelta
Deal found 6/11$248
This Southwest deal was found by Cheapflights users on 6/10. 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 7/226:55 pmPWM - MDW
Nonstop2h 35mSouthwest
Tue 8/511:40 amMDW - PWM
Nonstop2h 15mSouthwest
Deal found 6/10$254
This Delta deal was found by Cheapflights users on 6/11. 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 7/26:03 amPWM - STL
1 stop6h 28mDelta
Sat 7/51:30 pmSTL - PWM
1 stop7h 07mDelta
Deal found 6/11$317
This Sun Country Air deal was found by Cheapflights users on 6/12. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1712:58 pmPWM - ORD
1 stop26h 07mSun Country Air
Wed 7/2312:20 pmORD - PWM
1 stop22h 55mSun Country Air
Deal found 6/12$335
This Delta deal was found by Cheapflights users on 6/9. 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 6/111:59 pmPWM - MLI
2 stops9h 50mDelta
Tue 6/175:27 pmMLI - PWM
1 stop5h 59mDelta
Deal found 6/9$348
This Southwest deal was found by Cheapflights users on 6/11. 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 8/85:50 amPWM - STL
1 stop6h 40mSouthwest
Sat 8/2312:30 pmSTL - PWM
1 stop8h 30mSouthwest
Deal found 6/11$357
This CheapTicketsDeal deal was found by Cheapflights users on 6/9. 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 CheapTicketsDeal is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1012:51 pmPWM - MDW
1 stop6h 49mAlaska Airlines
Tue 8/126:04 amMDW - PWM
1 stop5h 25mAlaska Airlines
Deal found 6/9$368

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 June 12, 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

Thu 6/26

6:00 am-7:57 am

Nonstop2h 57m

Chicago O'Hare Intl

Mon 6/30

7:09 pm-10:47 pm

Nonstop2h 38m

$219

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 7/1

10:05 am-4:52 pm

1 stop7h 47m

Chicago O'Hare Intl

Wed 7/9

6:30 pm-10:01 pm

Nonstop2h 31m

$229

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 8/2

2:19 pm-10:28 pm

1 stop9h 09m

Chicago O'Hare Intl

Tue 8/5

6:10 am-1:23 pm

1 stop6h 13m

$233

PortlandChicago

PWM - ORD

PWMORD

Portland

Mon 6/30

6:56 pm-11:59 pm

1 stop6h 03m

Chicago O'Hare Intl

Sat 7/12

7:00 am-12:57 am

1 stop16h 57m

$235

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 7/1

5:30 am-11:50 am

1 stop7h 20m

Chicago O'Hare Intl

Fri 7/11

1:50 pm-12:05 am

1 stop9h 15m

$244

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 7/2

12:49 pm-6:41 pm

1 stop6h 52m

Chicago Midway

Wed 7/9

9:25 am-4:11 pm

1 stop5h 46m

$248

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 7/22

6:55 pm-8:30 pm

Nonstop2h 35m

Chicago Midway

Tue 8/5

11:40 am-2:55 pm

Nonstop2h 15m

$254

PortlandSt. Louis

PWM - STL

PWMSTL

Portland

Wed 7/2

6:03 am-11:31 am

1 stop6h 28m

Lambert-St Louis

Sat 7/5

1:30 pm-9:37 pm

1 stop7h 07m

$317

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 7/17

12:58 pm-2:05 pm

1 stop26h 07m

Chicago O'Hare Intl

Wed 7/23

12:20 pm-12:15 pm

1 stop22h 55m

$335

PortlandSt. Louis

PWM - STL

PWMSTL

Portland

Fri 8/8

5:50 am-11:30 am

1 stop6h 40m

Lambert-St Louis

Sat 8/23

12:30 pm-10:00 pm

1 stop8h 30m

$357

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 39 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 June 12, 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 June 12, 2025.

The most flights from PWM to USIL are scheduled on a Monday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).

Rainfall in Illinois by month

Plan your trip to Illinois by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Illinois ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Illinois when rainfall is around 1.7 in.

Temperature in Illinois by month

Plan your trip to Illinois by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Illinois, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest and Delta from Portland to Illinois by reading reviews from past customers. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,925 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 United Airlines, which is currently one of the cheapest options available, starting at $90. Southwest flights start at $90 while deals on JetBlue start at $97 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 (100%), Qatar Airways (99%), American Airlines (96%).

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

    Looking at all options, your cheapest flight can be booked for $129. While the most popular route (Portland - Chicago O'Hare Intl) can be booked for $219 on average our data indicates $796 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

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Top 5 airlines flying from Portland to Illinois

Discover the top 5 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$39Average$127FlexibilityNo cancel feeOn-time62%
DeltaCheapest$124Average$353FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$158Average$313FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$209Average$432FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$264Average$371FlexibilityNo cancel feeOn-time63%

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