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Portland

$110+ 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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This United Airlines deal was found by Cheapflights users on 12/16. 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 12/306:21 pmORD - PWM
1 stop4h 38mUnited Airlines
Fri 1/26:46 pmPWM - ORD
1 stop5h 49mUnited Airlines
Deal found 12/16$269
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Fri 12/266:21 pmORD - PWM
1 stop4h 38mUnited Airlines
Thu 8/206:20 pmPWM - ORD
Nonstop2h 57mUnited Airlines
Deal found 12/16$284
This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:35 amORD - PWM
1 stop4h 04mAmerican Airlines
Tue 1/65:07 pmPWM - ORD
1 stop6h 27mAmerican Airlines
Deal found 12/16$285
This Delta deal was found by Cheapflights users on 12/17. 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.
Thu 12/256:05 amSTL - PWM
2 stops9h 27mDelta
Wed 12/315:45 amPWM - STL
1 stop7h 36mDelta
Deal found 12/17$286
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Thu 12/2510:35 amORD - PWM
Nonstop2h 39mUnited Airlines
Wed 12/317:30 pmPWM - ORD
1 stop5h 14mUnited Airlines
Deal found 12/17$289
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Fri 12/266:21 pmORD - PWM
1 stop4h 38mUnited Airlines
Wed 1/1411:12 amPWM - ORD
1 stop6h 44mUnited Airlines
Deal found 12/16$294
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/3110:35 amORD - PWM
Nonstop2h 39mUnited Airlines
Tue 1/66:00 amPWM - ORD
1 stop8h 15mUnited Airlines
Deal found 12/16$309
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Wed 12/243:53 pmORD - PWM
1 stop6h 29mUnited Airlines
Wed 12/319:30 amPWM - ORD
Nonstop3h 14mUnited Airlines
Deal found 12/17$313
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Fri 12/266:21 pmORD - PWM
1 stop4h 38mUnited Airlines
Wed 5/64:45 pmPWM - ORD
Nonstop2h 57mUnited Airlines
Deal found 12/16$318
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Fri 12/266:21 pmORD - PWM
1 stop4h 38mUnited Airlines
Tue 1/2711:12 amPWM - ORD
1 stop8h 03mUnited Airlines
Deal found 12/16$328
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Thu 12/1810:35 amORD - PWM
Nonstop2h 39mUnited Airlines
Thu 1/156:00 amPWM - ORD
1 stop7h 05mUnited Airlines
Deal found 12/17$329
This Delta deal was found by Cheapflights users on 12/17. 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 12/313:29 pmMDW - PWM
1 stop6h 14mDelta
Tue 1/66:00 amPWM - MDW
2 stops13h 32mDelta
Deal found 12/17$339

Find flight deals from Illinois to Portland

Keep the following information in mind while searching for Illinois to Portland flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$209
(United Airlines)

One-way from

$110
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$266

Good round-trip deal

$300 or less

Good one-way deal

$358 or less
Provider with most accurate pricing for Chicago (CHI)-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Boston Logan Intl flights.
Search Deals
From Illinois to Portland
Search Deals
One-way flight from Illinois to Portland
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 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 Illinois to Portland.
Search Deals
Price to beat on a one-way flight from Illinois to Portland.
Search Deals

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 December 18, 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

Tue 2/3

11:00 am-2:39 pm

Nonstop2h 39m

Portland

Tue 2/10

4:10 pm-6:18 pm

Nonstop3h 08m

$209

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 1/8

11:00 am-2:39 pm

Nonstop2h 39m

Portland

Mon 1/12

4:10 pm-6:18 pm

Nonstop3h 08m

$209

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 4/4

9:37 am-4:10 pm

1 stop5h 33m

Portland

Tue 4/7

5:45 pm-10:12 pm

1 stop5h 27m

$229

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 1/11

6:50 am-12:08 pm

1 stop4h 18m

Portland

Wed 1/14

2:35 pm-9:35 pm

1 stop8h 00m

$229

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 1/13

5:20 pm-11:22 pm

1 stop5h 02m

Portland

Thu 1/15

5:57 pm-10:34 pm

1 stop5h 37m

$229

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Mon 1/12

5:20 pm-11:22 pm

1 stop5h 02m

Portland

Tue 1/20

5:57 pm-10:34 pm

1 stop5h 37m

$229

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 4/1

10:50 am-5:05 pm

1 stop5h 15m

Portland

Tue 4/7

5:45 pm-10:12 pm

1 stop5h 27m

$229

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 1/8

6:25 pm-12:20 am

1 stop4h 55m

Portland

Mon 1/12

5:57 pm-10:34 pm

1 stop5h 37m

$229

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 1/13

1:28 pm-11:22 pm

2 stops8h 54m

Portland

Wed 1/14

12:20 pm-5:34 pm

1 stop6h 14m

$234

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Mon 1/12

1:28 pm-11:22 pm

2 stops8h 54m

Portland

Tue 1/20

2:35 pm-10:22 pm

2 stops8h 47m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 51 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 $88). Flying from Illinois to Portland, Maine in February is currently the most expensive (average of $137). 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 December 18, 2025.

When flying from Illinois to Portland, Maine, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 25% versus a flight at noon.

What is the cheapest day to fly from Illinois to Portland, Maine?

Use this chart to determine the cheapest time to fly round-trip from Illinois to Portland. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Illinois to Portland, Maine flight should consider departing on Sunday afternoons when fares are most often at their lowest. Thursday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 American Airlines fly from Illinois to Portland, Maine in about 2h 39m. The time it takes to get you to your destination can typically vary by up to 2h 54m. 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 American Airlines. According to our data, you can fly for as low as $99. Users have also found prices from $108 and $115 on Delta and United Airlines, 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 Greater Peoria - 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: Air New Zealand (79%), SkyWest Airlines (74%), American Airlines( 65%).

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

    The cheapest flight price from Illinois to Portland, Maine is $195. On average you can expect to pay $419. The most popular route, (Chicago O'Hare Intl - Portland), can usually be booked for $209.

  • 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 $88). Flying from Illinois to Portland, Maine in February is currently the most expensive (average of $137). 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
North Conway
Brunswick
Auburn
Conway

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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$163Average$479FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$221Average$434FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$231Average$397FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$313Average$411FlexibilityNo cancel feeOn-time63%

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