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$115+ 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 4/3. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
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 February 4, 2026.

This United Airlines deal was found by Cheapflights users on 2/2. 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 9/161:55 pm
ORD
-
PWM
Nonstop2h 17m
United Airlines
Wed 9/236:00 am
PWM
-
ORD
Nonstop2h 57m
United Airlines
Deal found 2/2$209
This American Airlines deal was found by Cheapflights users on 2/3. 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.
Fri 3/208:02 pm
ORD
-
PWM
Nonstop2h 32m
American Airlines
Fri 3/276:17 am
PWM
-
ORD
Nonstop3h 17m
American Airlines
Deal found 2/3$210
This United Airlines deal was found by Cheapflights users on 2/2. 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 6/43:47 pm
ORD
-
PWM
1 stop7h 03m
United Airlines
Sun 6/76:00 am
PWM
-
ORD
Nonstop3h 00m
United Airlines
Deal found 2/2$219
This Delta deal was found by Cheapflights users on 2/1. 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 9/166:00 am
ORD
-
PWM
1 stop6h 21m
Delta
Sat 9/196:50 pm
PWM
-
ORD
1 stop6h 07m
Delta
Deal found 2/1$229
This Delta deal was found by Cheapflights users on 2/2. 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 4/299:27 am
MDW
-
PWM
1 stop5h 30m
Delta
Wed 5/1312:52 pm
PWM
-
MDW
1 stop6h 22m
Delta
Deal found 2/2$229
This JetBlue deal was found by Cheapflights users on 2/2. 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.
Thu 9/171:35 pm
ORD
-
PWM
1 stop7h 32m
JetBlue
Mon 9/217:09 am
PWM
-
ORD
1 stop6h 11m
JetBlue
Deal found 2/2$235
This United Airlines deal was found by Cheapflights users on 2/2. 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 3/274:30 pm
ORD
-
PWM
1 stop4h 48m
United Airlines
Mon 3/306:04 am
PWM
-
ORD
Nonstop2h 56m
United Airlines
Deal found 2/2$247
This Southwest deal was found by Cheapflights users on 2/1. 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 5/125:00 pm
MDW
-
PWM
1 stop4h 20m
Southwest
Sat 5/164:35 pm
PWM
-
MDW
1 stop5h 05m
Southwest
Deal found 2/1$247
This United Airlines deal was found by Cheapflights users on 2/1. 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 6/186:25 pm
ORD
-
PWM
Nonstop2h 33m
United Airlines
Tue 6/236:00 am
PWM
-
ORD
Nonstop3h 00m
United Airlines
Deal found 2/1$248
This Delta deal was found by Cheapflights users on 2/3. 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.
Fri 5/87:00 am
ORD
-
PWM
1 stop3h 57m
Delta
Sun 5/1012:52 pm
PWM
-
ORD
1 stop6h 21m
Delta
Deal found 2/3$249
This American Airlines deal was found by Cheapflights users on 2/2. 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.
Fri 5/87:49 pm
ORD
-
PWM
Nonstop2h 38m
American Airlines
Sun 5/105:51 pm
PWM
-
ORD
Nonstop3h 13m
American Airlines
Deal found 2/2$254
This United Airlines deal was found by Cheapflights users on 2/2. 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 8/116:00 pm
ORD
-
PWM
Nonstop2h 27m
United Airlines
Tue 8/187:22 pm
PWM
-
ORD
1 stop4h 53m
United Airlines
Deal found 2/2$257

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 February 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$209
(United Airlines)

One-way from

$115
(Delta)

Popular in

December

Cheapest in

February

Average price

$285

Good round-trip deal

$254 or less

Good one-way deal

$195 or less
Provider with most accurate pricing for Chicago (CHI)-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Portland 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. 10% potential increase in price ($40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 4, 2026.
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

Sat 5/30

6:25 pm-9:58 pm

Nonstop2h 33m

Portland

Sat 6/6

6:25 pm-8:34 pm

Nonstop3h 09m

$209

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 3/28

5:47 pm-9:04 pm

Nonstop2h 17m

Portland

Tue 3/31

6:04 am-8:00 am

Nonstop2h 56m

$209

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 6/4

3:47 pm-11:50 pm

1 stop7h 03m

Portland

Tue 6/9

6:00 am-8:00 am

Nonstop3h 00m

$219

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 4/29

8:52 am-3:57 pm

1 stop6h 05m

Portland

Wed 5/13

1:18 pm-7:09 pm

1 stop6h 51m

$229

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Wed 4/29

9:27 am-3:57 pm

1 stop5h 30m

Portland

Wed 5/13

12:52 pm-6:14 pm

1 stop6h 22m

$229

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 6/6

1:44 pm-12:34 am

2 stops9h 50m

Portland

Wed 6/10

12:50 pm-6:41 pm

1 stop6h 51m

$234

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Mon 3/2

2:05 pm-12:18 am

2 stops9h 13m

Portland

Mon 3/9

2:30 pm-11:54 pm

2 stops10h 24m

$239

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 3/6

3:46 pm-10:18 pm

1 stop5h 32m

Portland

Sun 3/8

6:00 am-10:49 am

1 stop5h 49m

$276

MolinePortland

MLI - PWM

MLIPWM

Moline Quad-City

Tue 3/10

6:30 am-2:32 pm

2 stops7h 02m

Portland

Tue 3/17

5:45 am-10:09 am

1 stop5h 24m

$276

BloomingtonPortland

BMI - PWM

BMIPWM

Bloomington-Normal

Mon 3/2

3:36 pm-11:06 pm

1 stop6h 30m

Portland

Mon 3/9

5:23 am-11:19 am

1 stop6h 56m

$279

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/1

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, September is the cheapest month in which you can book a flight from Illinois to Portland, Maine (average of $91). Flying from Illinois to Portland, Maine in July is currently the most expensive (average of $117). 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 February 4, 2026.

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 afternoon, which can drop the price by up to 25% versus a flight in the morning.

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 January 31, 2026.

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 33m. The time it takes to get you to your destination can typically vary by up to 3h 19m. 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 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: SkyWest Airlines (64%), United Airlines (61%), Republic Airways( 58%).

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

    The cheapest flight price from Illinois to Portland, Maine is $115. On average you can expect to pay $285. 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, September is the cheapest month in which you can book a flight from Illinois to Portland, Maine (average of $91). Flying from Illinois to Portland, Maine in July is currently the most expensive (average of $117). 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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Alternative routes for Illinois to Portland

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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 February 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$108Average$388FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$209Average$405FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$229Average$395FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$259Average$460FlexibilityNo cancel feeOn-time63%

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