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Portland

$96+ Cheap flights from Illinois to Portland, ME (PWM)

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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
1 adult, Economy
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Cheap flight deals from Illinois to Portland

Keep the following information in mind while searching for Illinois to Portland flight deals. Data was last updated septiembre 16, 2025.

Round-trip from

$238
(American Airlines)

One-way from

$96
(Priceline)

Popular in

December

Cheapest in

March

Average price

$319

Good round-trip deal

$280 or less

Good one-way deal

$188 or less
From Illinois to Portland
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One-way flight from Illinois to Portland
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Highest demand for flights based on searches. 10% potential increase in price ($43 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Illinois to Portland.
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Price to beat on a one-way flight from Illinois to Portland.
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Find flight deals from Illinois to Portland

Cheapest flights from Illinois to Portland
Explore the most affordable flight options available from Illinois to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 16, 2025.

This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/317:58 amORD - PWM
Nonstop2h 30mAmerican Airlines
vie. 10/313:38 pmPWM - ORD
1 stop6h 32mAmerican Airlines
Deal found 9/15$238
This American Airlines deal was found by Cheapflights users on 9/14. 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.
mié. 11/121:45 pmORD - PWM
1 stop6h 50mAmerican Airlines
sáb. 11/155:37 pmPWM - ORD
Nonstop3h 13mAmerican Airlines
Deal found 9/14$241
This Delta deal was found by Cheapflights users on 9/15. 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.
mié. 11/126:00 amMDW - PWM
1 stop5h 30mDelta
sáb. 11/1512:48 pmPWM - MDW
1 stop6h 20mDelta
Deal found 9/15$251
This Expedia deal was found by Cheapflights users on 9/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/306:45 amORD - PWM
1 stop5h 37mJetBlue
sáb. 10/47:09 amPWM - ORD
1 stop12h 14mJetBlue
Deal found 9/15$253
This American Airlines deal was found by Cheapflights users on 9/14. 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.
sáb. 11/221:10 pmORD - PWM
1 stop7h 37mAmerican Airlines
jue. 11/277:02 amPWM - ORD
1 stop6h 54mAmerican Airlines
Deal found 9/14$254
This American Airlines deal was found by Cheapflights users on 9/14. 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.
mié. 11/121:40 pmORD - PWM
Nonstop2h 25mAmerican Airlines
dom. 11/165:37 pmPWM - ORD
Nonstop3h 13mAmerican Airlines
Deal found 9/14$255
This Delta deal was found by Cheapflights users on 9/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/125:32 amORD - PWM
1 stop5h 58mDelta
sáb. 11/1512:10 pmPWM - ORD
2 stops9h 19mDelta
Deal found 9/16$256
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/3111:30 amORD - PWM
Nonstop2h 26mAmerican Airlines
lun. 11/35:21 pmPWM - ORD
1 stop5h 02mAmerican Airlines
Deal found 9/15$260
This Delta deal was found by Cheapflights users on 9/15. 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.
mar. 10/2111:02 amORD - PWM
2 stops11h 07mDelta
sáb. 10/256:30 amPWM - ORD
2 stops11h 20mDelta
Deal found 9/15$261
This Expedia deal was found by Cheapflights users on 9/13. 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.
mié. 10/11:35 pmORD - PWM
1 stop7h 31mJetBlue
sáb. 10/47:09 amPWM - ORD
1 stop12h 14mJetBlue
Deal found 9/13$263
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/16:10 pmORD - PWM
Nonstop2h 34mUnited Airlines
mar. 10/75:41 pmPWM - ORD
1 stop6h 49mUnited Airlines
Deal found 9/15$265
This JetBlue deal was found by Cheapflights users on 9/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/76:45 amORD - PWM
1 stop5h 37mJetBlue
mié. 10/157:30 amPWM - ORD
1 stop5h 40mJetBlue
Deal found 9/16$269

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois to Portland 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 septiembre 16, 2025.
Use the filters below to find and compare flights from Illinois to Portland that are best for you.

Fly from

Illinois

Fly to

Portland

Route

Depart

Return

Price

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

mar. 10/7

4:50 pm-11:13 pm

1 stop5h 23m

Portland

mar. 10/14

5:41 pm-11:30 pm

1 stop6h 49m

$251

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

mié. 11/12

6:00 am-12:30 pm

1 stop5h 30m

Portland

sáb. 11/15

6:00 am-3:43 pm

2 stops10h 43m

$256

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

vie. 11/14

5:31 pm-11:17 pm

1 stop4h 46m

Portland

mar. 11/18

4:51 pm-6:52 pm

Nonstop3h 01m

$265

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

sáb. 12/6

1:04 pm-10:17 pm

1 stop8h 13m

Portland

dom. 12/7

2:34 pm-5:46 pm

1 stop28h 12m

$273

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

sáb. 12/6

6:45 am-12:08 pm

1 stop4h 23m

Portland

lun. 12/8

6:15 am-5:46 pm

1 stop12h 31m

$273

MolinePortland

MLI - PWM

MLIPWM

Moline Quad-City

mié. 10/1

3:40 pm-9:44 pm

1 stop5h 04m

Portland

mar. 10/7

6:14 am-10:15 am

1 stop5h 01m

$274

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

mar. 3/3

7:30 am-1:51 pm

1 stop5h 21m

Portland

mié. 3/4

6:00 am-10:22 am

1 stop5h 22m

$275

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

sáb. 10/4

6:10 pm-9:44 pm

Nonstop2h 34m

Portland

vie. 10/10

6:25 pm-8:25 pm

Nonstop3h 00m

$279

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

mié. 10/1

6:10 pm-9:44 pm

Nonstop2h 34m

Portland

sáb. 10/4

6:14 am-8:05 am

Nonstop2h 51m

$279

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

mié. 11/5

5:20 am-4:03 pm

2 stops9h 43m

Portland

lun. 11/10

4:53 pm-8:29 pm

1 stop4h 36m

$280

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 60 results
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Best time to book a flight from Illinois to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Illinois 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 Illinois to Portland

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

Currently, January is the cheapest month in which you can book a flight from Illinois to Portland, Maine (average of $296). Flying from Illinois to Portland, Maine in July is currently the most expensive (average of $394). 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 IL to PWM?

Find hourly flight availability from Illinois to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 16, 2025.

When flying from Illinois to Portland, Maine, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Illinois to Portland, Maine

Explore weekly flight availability from Illinois to Portland. 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 septiembre 16, 2025.

The most flights from USIL to PWM are scheduled on a Monday (11 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (9 on average).

Related info for your journey

Find useful and relevant information for your journey from Illinois to Portland. 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 into for flights to Portland from Illinois?

    For a flight from Illinois to Portland, you will be flying into Portland. Portland (PWM) is just 2.9 mi from the center of the city.

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

    Airlines like United Airlines, Delta, and Southwest fly from Illinois to Portland, Maine in about 5h 23m. The time it takes to get you to your destination can typically vary by up to 4h 07m. Illinois and Portland, Maine are separated by a distance of 897 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $116. Users have also found prices from $116 and $126 on Southwest and Delta, respectively.

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

    The most popular flight routes from Illinois to Portland, Maine are Chicago O'Hare Intl - Portland, Chicago Midway - Portland and Lambert-St Louis - Portland.

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

    Before booking your flight to Portland, Maine from Illinois, check out the most reliable airlines to get you to your destination on time: Envoy Air (100%), SkyWest Airlines (74%), United Airlines( 72%).

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

    The cheapest flight price from Illinois to Portland, Maine is $129. On average you can expect to pay $282. The most popular route, (Chicago O'Hare Intl - Portland), can usually be booked for $214.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Illinois to Portland 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 Illinois to Portland, Maine?

    Currently, January is the cheapest month in which you can book a flight from Illinois to Portland, Maine (average of $296). Flying from Illinois to Portland, Maine in July is currently the most expensive (average of $394). 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

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
Brunswick
North Conway
Auburn
Conway
Lewiston

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Top 4 airlines flying from Illinois to Portland

Discover the top 4 airlines that operate flights from Illinois to Portland. 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 septiembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$163Average$479FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$228Average$442FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$232Average$395FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$276Average$411FlexibilityNo cancel feeOn-time63%

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