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$72+ 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 4/13. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$110
(Frontier)

One-way from

$72
(Mytrip)

Popular in

April

Cheapest in

June

Average price

$357

Good round-trip deal

$331 or less

Good one-way deal

$288 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
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($50 potential increase over avg. RT price).
Search Deals
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 February 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 February 20, 2025.

This JetBlue deal was found by Cheapflights users on 2/20. 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.
Mon 8/186:00 amORD - PWM
1 stop6h 23mJetBlue
Mon 8/256:10 amPWM - ORD
1 stop5h 37mJetBlue
Deal found 2/20$163
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Sat 7/56:20 pmORD - PWM
Nonstop2h 30mAmerican Airlines
Wed 7/97:19 amPWM - ORD
Nonstop2h 51mAmerican Airlines
Deal found 2/20$209
This Delta deal was found by Cheapflights users on 2/20. 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 3/196:00 amORD - PWM
1 stop4h 27mDelta
Wed 3/264:30 pmPWM - ORD
1 stop5h 08mDelta
Deal found 2/20$217
This Southwest deal was found by Cheapflights users on 2/20. 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 5/136:20 amMDW - PWM
1 stop4h 10mSouthwest
Tue 5/202:20 pmPWM - MDW
1 stop6h 30mSouthwest
Deal found 2/20$217
This United Airlines deal was found by Cheapflights users on 2/19. 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 3/511:10 amORD - PWM
Nonstop2h 22mUnited Airlines
Fri 4/256:00 amPWM - ORD
Nonstop2h 52mUnited Airlines
Deal found 2/19$220
This Southwest deal was found by Cheapflights users on 2/20. 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 5/131:50 pmORD - PWM
1 stop7h 40mSouthwest
Tue 5/206:15 amPWM - ORD
2 stops7h 30mSouthwest
Deal found 2/20$244
This CheapOair deal was found by Cheapflights users on 2/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/278:04 amORD - PWM
1 stop24h 49mFrontier
Tue 3/410:08 amPWM - ORD
1 stop24h 19mFrontier
Deal found 2/20$260
This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/85:24 pmSTL - PWM
1 stop14h 24mFrontier
Sat 3/1510:08 amPWM - STL
1 stop22h 50mFrontier
Deal found 2/20$269
This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/78:00 amORD - PWM
2 stops29h 29mMultiple Airlines
Fri 5/96:16 pmPWM - ORD
2 stops14h 24mMultiple Airlines
Deal found 2/20$274
This Delta deal was found by Cheapflights users on 2/20. 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 9/31:00 pmMDW - PWM
2 stops9h 45mDelta
Tue 9/912:30 pmPWM - MDW
1 stop6h 33mDelta
Deal found 2/20$284
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Thu 4/31:38 pmSTL - PWM
1 stop8h 06mAmerican Airlines
Mon 4/77:20 amPWM - STL
1 stop8h 25mAmerican Airlines
Deal found 2/20$315
This CheapOair deal was found by Cheapflights users on 2/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2412:43 pmMDW - PWM
1 stop19h 35mFrontier
Wed 2/266:48 pmPWM - MDW
1 stop28h 58mFrontier
Deal found 2/20$320

Find flights from Illinois to Portland within your budget

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 20, 2025.

Fly from

Illinois

Fly to

Portland

Route

Depart

Return

Price

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Mon 8/18

6:00 am-1:23 pm

1 stop6h 23m

Portland

Tue 8/26

6:10 am-10:47 am

1 stop5h 37m

$163

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 7/5

6:20 pm-9:50 pm

Nonstop2h 30m

Portland

Wed 7/9

7:19 am-9:10 am

Nonstop2h 51m

$209

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 3/19

6:00 am-11:27 am

1 stop4h 27m

Portland

Wed 3/26

4:30 pm-8:38 pm

1 stop5h 08m

$217

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 5/13

6:20 am-11:30 am

1 stop4h 10m

Portland

Tue 5/20

2:20 pm-7:50 pm

1 stop6h 30m

$217

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 3/5

11:10 am-2:32 pm

Nonstop2h 22m

Portland

Fri 4/25

6:00 am-7:52 am

Nonstop2h 52m

$220

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 5/13

1:50 pm-10:30 pm

1 stop7h 40m

Portland

Tue 5/20

6:15 am-12:45 pm

2 stops7h 30m

$244

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Mon 3/3

7:08 pm-9:18 am

1 stop13h 10m

Portland

Wed 3/5

6:48 pm-3:10 pm

1 stop21h 22m

$260

St. LouisPortland

STL - PWM

STLPWM

Lambert-St Louis

Sat 3/8

5:24 pm-8:48 am

1 stop14h 24m

Portland

Sat 3/15

10:08 am-7:58 am

1 stop22h 50m

$269

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 5/7

8:00 am-2:29 pm

2 stops29h 29m

Portland

Fri 5/9

6:16 pm-7:40 am

2 stops14h 24m

$274

St. LouisPortland

STL - PWM

STLPWM

Lambert-St Louis

Thu 4/3

1:38 pm-10:44 pm

1 stop8h 06m

Portland

Mon 4/7

7:20 am-2:45 pm

1 stop8h 25m

$315

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 41 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.

Travel insights for flights from Illinois to Portland

Get recent, data-driven insights about flights from Illinois to Portland including ideal travel times, pricing trends, and more.

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 April is currently the most expensive (average of $498). 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 20, 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 February 20, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and JetBlue 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
8.1
Very good
4,411 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 Frontier. According to our data, you can fly for as low as $72. Users have also found prices from $82 and $105 on JetBlue and American 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: Republic Airways (92%), United Airlines (88%), SkyWest Airlines( 72%).

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

    The cheapest flight price from Illinois to Portland, Maine is $223. On average you can expect to pay $385. The most popular route, (Chicago O'Hare Intl - Portland), can usually be booked for $163.

  • 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 April is currently the most expensive (average of $498). 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

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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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$92FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$179Average$441FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$191Average$401FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$350FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$220Average$414FlexibilityNo cancel feeOn-time69%
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