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Portland

$90+ 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 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$251
(American Airlines)

One-way from

$90
(American Airlines)

Popular in

April

Cheapest in

February

Average price

$329

Good round-trip deal

$289 or less

Good one-way deal

$139 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. 4% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Booking.com deal was found by Cheapflights users on 4/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/75:45 pmSTL - PWM
1 stop25h 44mFrontier
Sun 5/118:23 pmPWM - STL
1 stop28h 43mFrontier
Deal found 4/30$228
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Tue 6/37:19 amORD - PWM
1 stop7h 17mAmerican Airlines
Tue 6/104:02 pmPWM - ORD
1 stop5h 07mAmerican Airlines
Deal found 4/30$251
This Delta deal was found by Cheapflights users on 4/30. 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.
Tue 7/15:27 pmMLI - PWM
1 stop5h 59mDelta
Wed 7/91:59 pmPWM - MLI
2 stops9h 47mDelta
Deal found 4/30$253
This Delta deal was found by Cheapflights users on 4/30. 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.
Wed 5/147:00 amORD - PWM
1 stop5h 50mDelta
Mon 5/195:30 amPWM - ORD
2 stops8h 11mDelta
Deal found 4/30$254
This Southwest deal was found by Cheapflights users on 4/30. 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.
Tue 5/278:15 amMDW - PWM
1 stop4h 10mSouthwest
Thu 5/292:30 pmPWM - MDW
2 stops6h 45mSouthwest
Deal found 4/30$254
This Delta deal was found by Cheapflights users on 4/30. 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.
Wed 5/141:55 pmMDW - PWM
2 stops9h 04mDelta
Mon 5/195:30 amPWM - MDW
2 stops7h 58mDelta
Deal found 4/30$259
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Tue 6/106:00 amPIA - PWM
1 stop4h 29mAmerican Airlines
Sat 6/146:01 pmPWM - PIA
1 stop6h 58mAmerican Airlines
Deal found 4/30$259
This Frontier deal was found by Cheapflights users on 4/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/149:08 amORD - PWM
1 stop8h 22mFrontier
Sat 6/217:25 pmPWM - ORD
1 stop12h 44mFrontier
Deal found 4/30$262
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/287:10 amORD - PWM
Nonstop2h 39mUnited Airlines
Mon 6/26:00 amPWM - ORD
Nonstop2h 53mUnited Airlines
Deal found 4/30$264
This JetBlue deal was found by Cheapflights users on 4/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/81:35 pmORD - PWM
1 stop7h 24mJetBlue
Sun 10/127:30 amPWM - ORD
1 stop6h 10mJetBlue
Deal found 4/30$275
This Southwest deal was found by Cheapflights users on 4/30. 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.
Fri 6/61:50 pmORD - PWM
1 stop9h 15mSouthwest
Tue 6/105:30 amPWM - ORD
2 stops8h 15mSouthwest
Deal found 4/30$280
This Delta deal was found by Cheapflights users on 4/29. 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.
Tue 6/243:42 pmSTL - PWM
1 stop7h 44mDelta
Wed 7/94:50 pmPWM - STL
1 stop5h 07mDelta
Deal found 4/29$285

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 May 1, 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

St. LouisPortland

STL - PWM

STLPWM

Lambert-St Louis

Wed 5/7

5:45 pm-8:29 pm

1 stop25h 44m

Portland

Sun 5/11

8:23 pm-12:06 am

1 stop28h 43m

$228

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 6/3

7:19 am-3:36 pm

1 stop7h 17m

Portland

Tue 6/10

4:02 pm-8:09 pm

1 stop5h 07m

$251

MolinePortland

MLI - PWM

MLIPWM

Moline Quad-City

Tue 7/1

5:27 pm-12:26 am

1 stop5h 59m

Portland

Wed 7/9

1:59 pm-10:46 pm

2 stops9h 47m

$253

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 5/27

8:15 am-1:25 pm

1 stop4h 10m

Portland

Thu 5/29

2:30 pm-8:15 pm

2 stops6h 45m

$254

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 5/14

7:00 am-1:50 pm

1 stop5h 50m

Portland

Mon 5/19

5:30 am-12:41 pm

2 stops8h 11m

$254

PeoriaPortland

PIA - PWM

PIAPWM

Greater Peoria

Tue 6/10

6:00 am-11:29 am

1 stop4h 29m

Portland

Sat 6/14

6:01 pm-11:59 pm

1 stop6h 58m

$259

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Wed 5/14

1:55 pm-11:59 pm

2 stops9h 04m

Portland

Mon 5/19

5:30 am-12:28 pm

2 stops7h 58m

$259

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 6/14

9:08 am-6:30 pm

1 stop8h 22m

Portland

Sat 6/21

7:25 pm-7:09 am

1 stop12h 44m

$262

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 5/28

7:10 am-10:49 am

Nonstop2h 39m

Portland

Mon 6/2

6:00 am-7:53 am

Nonstop2h 53m

$264

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 10/8

1:35 pm-9:59 pm

1 stop7h 24m

Portland

Sun 10/12

7:30 am-12:40 pm

1 stop6h 10m

$275

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 44 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 May is currently the most expensive (average of $405). 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 May 1, 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.

Rainfall in Portland by month

Plan your trip to Portland by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Portland, Maine ranges from 2.9 - 4.5 inches per month. November is typically the wettest month, when rainfall can reach 4.5 in. August is typically the driest time to visit Portland, Maine when rainfall is around 2.9 in.

Temperature in Portland by month

Plan your trip to Portland by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Portland, Maine, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 May 1, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and United Airlines from Illinois to Portland to help guide your decision. 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
4,294 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,924 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Comfort

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 $90. Users have also found prices from $100 and $101 on United Airlines 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: SkyWest Airlines (84%), Air New Zealand (84%), Republic Airways( 74%).

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

    The cheapest flight price from Illinois to Portland, Maine is $104. On average you can expect to pay $272. The most popular route, (Chicago O'Hare Intl - Portland), can usually be booked for $192.

  • 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 May is currently the most expensive (average of $405). 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 Illinois?

Book flights to Illinois if you plan to visit one of these locations
North Conway
Bath
Brunswick
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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$87FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$178Average$421FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$191Average$406FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$212Average$467FlexibilityNo cancel feeOn-time69%
DeltaCheapest$228Average$479FlexibilityNo cancel feeOn-timeN/A

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