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Portland

$111+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
nov. 29 — dic. 61
sáb. 11/29
sáb. 12/6
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 octubre 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$249
(Delta)

One-way from

$111
(Kiwi.com)

Popular in

November

Cheapest in

March

Average price

$381

Good round-trip deal

$391 or less

Good one-way deal

$230 or less
Provider with most accurate pricing for Chicago (CHI)-Portland flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Portland flights.
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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. 14% potential increase in price ($64 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 October 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 octubre 30, 2025.

This Delta deal was found by Cheapflights users on 10/28. 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. 11/121:29 pmORD - PWM
1 stop7h 50mDelta
mar. 11/1811:25 amPWM - ORD
1 stop7h 55mDelta
Deal found 10/28$249
This Delta deal was found by Cheapflights users on 10/28. 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
mar. 11/186:00 amPWM - MDW
1 stop6h 52mDelta
Deal found 10/28$249
This Delta deal was found by Cheapflights users on 10/28. 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. 11/111:29 pmORD - PWM
2 stops8h 50mDelta
mar. 11/184:53 pmPWM - ORD
1 stop4h 36mDelta
Deal found 10/28$254
This Delta deal was found by Cheapflights users on 10/28. 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. 11/1112:47 pmMDW - PWM
2 stops10h 07mDelta
mar. 11/186:00 amPWM - MDW
1 stop6h 52mDelta
Deal found 10/28$254
This United Airlines deal was found by Cheapflights users on 10/29. 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.
jue. 11/1310:53 amORD - PWM
Nonstop2h 19mUnited Airlines
lun. 11/1710:45 amPWM - ORD
1 stop6h 39mUnited Airlines
Deal found 10/29$259
This Delta deal was found by Cheapflights users on 10/28. 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.
vie. 11/141:15 pmMDW - PWM
2 stops9h 39mDelta
mar. 11/1811:25 amPWM - MDW
2 stops7h 43mDelta
Deal found 10/28$259
This United Airlines deal was found by Cheapflights users on 10/29. 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.
mar. 11/1812:00 pmORD - PWM
1 stop4h 48mUnited Airlines
sáb. 11/227:22 pmPWM - ORD
1 stop5h 21mUnited Airlines
Deal found 10/29$268
This Delta deal was found by Cheapflights users on 10/29. 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.
mié. 11/126:00 amMDW - PWM
1 stop5h 30mDelta
sáb. 11/1512:48 pmPWM - MDW
1 stop6h 20mDelta
Deal found 10/29$269
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/712:09 pmORD - PWM
1 stop19h 57mMultiple Airlines
vie. 1/911:29 amPWM - ORD
2 stops37h 32mMultiple Airlines
Deal found 10/30$272
This Delta deal was found by Cheapflights users on 10/29. 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.
mié. 11/122:35 pmORD - PWM
2 stops7h 44mDelta
sáb. 11/156:00 amPWM - ORD
1 stop7h 04mDelta
Deal found 10/29$274
This Delta deal was found by Cheapflights users on 10/29. 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.
mar. 11/1111:19 amORD - PWM
2 stops11h 35mDelta
sáb. 11/156:00 amPWM - ORD
2 stops12h 17mDelta
Deal found 10/29$279
This Delta deal was found by Cheapflights users on 10/29. 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.
mar. 11/1110:47 amMDW - PWM
2 stops12h 07mDelta
sáb. 11/156:00 amPWM - MDW
2 stops10h 43mDelta
Deal found 10/29$279

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 octubre 30, 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. 11/18

3:07 pm-11:01 pm

1 stop6h 54m

Portland

dom. 11/23

5:30 am-9:46 am

1 stop5h 16m

$249

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

jue. 11/13

9:34 am-4:07 pm

1 stop5h 33m

Portland

mar. 11/18

6:00 am-11:52 am

1 stop6h 52m

$249

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

jue. 11/13

10:53 am-2:12 pm

Nonstop2h 19m

Portland

lun. 11/17

5:00 pm-6:55 pm

Nonstop2h 55m

$249

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

mar. 3/3

5:50 am-3:56 pm

2 stops9h 06m

Portland

mié. 3/4

6:00 am-10:22 am

1 stop5h 22m

$254

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

jue. 11/27

5:23 am-12:30 pm

1 stop6h 07m

Portland

jue. 12/4

6:15 am-4:45 pm

2 stops11h 30m

$254

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

mié. 11/12

1:29 pm-11:54 pm

2 stops9h 25m

Portland

mar. 11/18

2:30 pm-9:27 pm

1 stop7h 57m

$254

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

mar. 11/11

12:47 pm-11:54 pm

2 stops10h 07m

Portland

mar. 11/18

6:00 am-11:52 am

1 stop6h 52m

$254

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

mar. 11/18

12:00 pm-5:48 pm

1 stop4h 48m

Portland

sáb. 11/22

4:57 pm-6:52 pm

Nonstop2h 55m

$259

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

vie. 11/14

1:15 pm-11:54 pm

2 stops9h 39m

Portland

mié. 11/19

6:00 am-4:39 pm

2 stops11h 39m

$259

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

vie. 11/14

6:20 pm-11:59 pm

1 stop4h 39m

Portland

mar. 11/18

7:22 pm-11:43 pm

1 stop5h 21m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

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, November is the cheapest month in which you can book a flight from Illinois to Portland, Maine (average of $71). 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 octubre 30, 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 Southwest fly from Illinois to Portland, Maine in about 4h 15m. The time it takes to get you to your destination can typically vary by up to 2h 39m. Illinois and Portland, Maine are separated by a distance of 1092 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 Delta. According to our data, you can fly for as low as $115. Users have also found prices from $115 and $199 on Southwest 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: Air New Zealand (82%), SkyWest Airlines (71%), American Airlines( 71%).

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

    The cheapest flight price from Illinois to Portland, Maine is $165. On average you can expect to pay $404. 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, November is the cheapest month in which you can book a flight from Illinois to Portland, Maine (average of $71). 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 octubre 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$163Average$479FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$226Average$435FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$232Average$397FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$313Average$411FlexibilityNo cancel feeOn-time63%

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