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$100+ 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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$233
(Delta)

One-way from

$100
(American Airlines)

Popular in

December

Cheapest in

February

Average price

$378

Good round-trip deal

$215 or less

Good one-way deal

$151 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. 9% potential increase in price ($37 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 July 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 July 31, 2025.

This Delta deal was found by Cheapflights users on 7/29. 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.
Sat 8/232:25 pmORD - PWM
2 stops8h 38mDelta
Sat 8/305:30 pmPWM - ORD
1 stop7h 26mDelta
Deal found 7/29$233
This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/231:08 pmMDW - PWM
2 stops9h 55mDelta
Sat 8/3011:48 amPWM - MDW
1 stop6h 49mDelta
Deal found 7/30$233
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/310:05 amORD - PWM
Nonstop2h 37mAmerican Airlines
Tue 9/96:00 amPWM - ORD
1 stop6h 06mAmerican Airlines
Deal found 7/30$234
This FlightHub deal was found by Cheapflights users on 7/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/84:26 pmORD - PWM
1 stop24h 47mFrontier
Sat 8/231:41 pmPWM - ORD
1 stop30h 00mFrontier
Deal found 7/29$235
This United Airlines deal was found by Cheapflights users on 7/29. 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.
Thu 9/46:25 pmORD - PWM
Nonstop2h 34mUnited Airlines
Tue 9/96:00 amPWM - ORD
1 stop8h 08mUnited Airlines
Deal found 7/29$248
This Southwest deal was found by Cheapflights users on 7/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/85:40 amMDW - PWM
1 stop6h 35mSouthwest
Wed 9/1010:30 amPWM - MDW
Nonstop2h 30mSouthwest
Deal found 7/30$248
This Trip.com deal was found by Cheapflights users on 7/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/161:36 pmORD - PWM
1 stop7h 26mJetBlue
Sun 10/197:09 amPWM - ORD
1 stop6h 01mJetBlue
Deal found 7/30$253
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/58:19 amMLI - PWM
1 stop6h 58mAmerican Airlines
Fri 9/125:10 pmPWM - MLI
1 stop6h 15mAmerican Airlines
Deal found 7/30$259
This American Airlines deal was found by Cheapflights users on 7/31. 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.
Sun 9/145:30 amPIA - PWM
1 stop7h 23mAmerican Airlines
Sat 9/205:10 pmPWM - PIA
1 stop7h 01mAmerican Airlines
Deal found 7/31$259
This Southwest deal was found by Cheapflights users on 7/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/41:50 pmORD - PWM
1 stop5h 10mSouthwest
Tue 9/95:50 amPWM - ORD
2 stops13h 05mSouthwest
Deal found 7/29$263
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/84:55 pmSTL - PWM
1 stop5h 10mAmerican Airlines
Sat 9/136:15 amPWM - STL
1 stop16h 38mAmerican Airlines
Deal found 7/30$297
This Delta deal was found by Cheapflights users on 7/29. 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.
Mon 9/86:00 amSTL - PWM
1 stop5h 58mDelta
Sat 9/1311:45 amPWM - STL
2 stops11h 15mDelta
Deal found 7/29$302

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 July 31, 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

Sat 8/23

2:25 pm-12:03 am

2 stops8h 38m

Portland

Sat 8/30

5:30 pm-11:56 pm

1 stop7h 26m

$233

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Sat 8/23

1:08 pm-12:03 am

2 stops9h 55m

Portland

Sat 8/30

11:48 am-5:37 pm

1 stop6h 49m

$233

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 9/3

10:05 am-1:42 pm

Nonstop2h 37m

Portland

Tue 9/9

1:02 pm-5:51 pm

1 stop5h 49m

$234

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 8/15

4:26 pm-6:13 pm

1 stop24h 47m

Portland

Sat 8/23

1:41 pm-6:41 pm

1 stop30h 00m

$235

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 9/4

6:25 pm-9:59 pm

Nonstop2h 34m

Portland

Tue 9/9

6:00 am-1:08 pm

1 stop8h 08m

$248

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Mon 9/8

5:40 am-1:15 pm

1 stop6h 35m

Portland

Wed 9/10

10:30 am-12:00 pm

Nonstop2h 30m

$248

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 10/16

1:36 pm-10:02 pm

1 stop7h 26m

Portland

Sun 10/19

7:09 am-12:10 pm

1 stop6h 01m

$253

MolinePortland

MLI - PWM

MLIPWM

Moline Quad-City

Fri 9/5

8:19 am-4:17 pm

1 stop6h 58m

Portland

Fri 9/12

5:10 pm-10:25 pm

1 stop6h 15m

$259

PeoriaPortland

PIA - PWM

PIAPWM

Greater Peoria

Sun 9/14

5:30 am-1:53 pm

1 stop7h 23m

Portland

Sat 9/20

5:10 pm-11:11 pm

1 stop7h 01m

$259

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 9/4

1:50 pm-8:00 pm

1 stop5h 10m

Portland

Tue 9/9

5:50 am-5:55 pm

2 stops13h 05m

$263

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 40 results
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2
3
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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 July 31, 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 July 31, 2025.

The most flights from USIL to PWM are scheduled on a Thursday (10 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (5 on average).

How much does it cost to fly round-trip from Illinois to Portland, Maine?

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated July 31, 2025.
Read through reviews of airlines operating flights from Illinois to Portland, such as Southwest, Delta, and United Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
JetBlue
7.3
Good
2,914 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • 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 $100. Users have also found prices from $100 and $102 on Southwest and JetBlue, 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 (90%), American Airlines (77%), Air New Zealand( 76%).

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

    The cheapest flight price from Illinois to Portland, Maine is $100. On average you can expect to pay $286. The most popular route, (Chicago O'Hare Intl - Portland), can usually be booked for $193.

  • 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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Alternative routes for Illinois to Portland

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Illinois to Portland

Discover the top 5 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$68Average$160FlexibilityNo cancel feeOn-time62%
DeltaCheapest$163Average$479FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$191Average$406FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$203Average$385FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$213Average$467FlexibilityNo cancel feeOn-time69%

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