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$124+ Cheap flights from Portland, ME (PWM) to Illinois

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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ORD
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
1 adult, Economy
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Cheap flight deals from Portland to Illinois

Keep the following information in mind while searching for Portland to Illinois flight deals. Data was last updated September 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$226
(Trip.com)

One-way from

$124
(American Airlines)

Popular in

April

Cheapest in

January

Average price

$200

Good round-trip deal

$318 or less

Good one-way deal

$177 or less
Provider with most accurate pricing for Boston Logan Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago (CHI) flights.
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From Portland to Illinois
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One-way flight from Portland to Illinois
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Highest demand for flights based on searches. 8% potential increase in price ($22 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Portland to Illinois.
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Price to beat on a one-way flight from Portland to Illinois.
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Find flight deals from Portland to Illinois

Cheapest flights from Portland to Illinois
Explore the most affordable flight options available from Portland to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 29, 2025.

This Trip.com deal was found by Cheapflights users on 9/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/217:09 amPWM - ORD
1 stop6h 13mJetBlue
Thu 10/231:35 pmORD - PWM
1 stop8h 29mJetBlue
Deal found 9/28$226
This United Airlines deal was found by Cheapflights users on 9/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/284:51 pmPWM - ORD
Nonstop3h 01mUnited Airlines
Tue 11/412:00 pmORD - PWM
1 stop4h 48mUnited Airlines
Deal found 9/28$257
This American Airlines deal was found by Cheapflights users on 9/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/255:59 pmPWM - MLI
1 stop6h 56mAmerican Airlines
Tue 10/286:00 amMLI - PWM
1 stop4h 28mAmerican Airlines
Deal found 9/28$259
This American Airlines deal was found by Cheapflights users on 9/27. 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 11/183:36 pmPWM - STL
1 stop6h 24mAmerican Airlines
Tue 12/22:05 pmSTL - PWM
1 stop6h 30mAmerican Airlines
Deal found 9/27$263
This American Airlines deal was found by Cheapflights users on 9/27. 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 10/2512:59 pmPWM - ORD
1 stop9h 20mAmerican Airlines
Tue 10/2811:13 amORD - PWM
1 stop8h 01mAmerican Airlines
Deal found 9/27$263
This Delta deal was found by Cheapflights users on 9/29. 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 10/256:30 amPWM - MLI
2 stops10h 50mDelta
Tue 10/286:00 amMLI - PWM
1 stop5h 22mDelta
Deal found 9/29$264
This American Airlines deal was found by Cheapflights users on 9/27. 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 11/45:37 pmPWM - ORD
Nonstop3h 13mAmerican Airlines
Tue 11/111:40 pmORD - PWM
Nonstop2h 25mAmerican Airlines
Deal found 9/27$265
This Delta deal was found by Cheapflights users on 9/28. 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.
Wed 11/51:46 pmPWM - ORD
1 stop6h 39mDelta
Wed 11/126:45 amORD - PWM
1 stop4h 23mDelta
Deal found 9/28$267
This Delta deal was found by Cheapflights users on 9/28. 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.
Tue 11/1112:48 pmPWM - MDW
1 stop6h 20mDelta
Wed 11/129:34 amMDW - PWM
1 stop5h 33mDelta
Deal found 9/28$267
This JetBlue deal was found by Cheapflights users on 9/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/157:09 amPWM - ORD
1 stop6h 13mJetBlue
Tue 10/211:35 pmORD - PWM
1 stop8h 29mJetBlue
Deal found 9/29$269
This Delta deal was found by Cheapflights users on 9/27. 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 11/512:45 pmPWM - MDW
1 stop6h 40mDelta
Wed 11/121:15 pmMDW - PWM
2 stops9h 39mDelta
Deal found 9/27$272
This American Airlines deal was found by Cheapflights users on 9/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/275:59 pmPWM - ORD
1 stop6h 54mAmerican Airlines
Wed 10/297:58 amORD - PWM
Nonstop2h 30mAmerican Airlines
Deal found 9/28$275

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Illinois 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 September 29, 2025.
Use the filters below to find and compare flights from Portland to Illinois that are best for you.

Fly from

Portland

Fly to

Illinois

Route

Depart

Return

Price

PortlandMoline

PWM - MLI

PWMMLI

Portland

Sat 10/25

5:59 pm-11:55 pm

1 stop6h 56m

Moline Quad-City

Tue 10/28

6:00 am-11:28 am

1 stop4h 28m

$259

PortlandSt. Louis

PWM - STL

PWMSTL

Portland

Tue 11/18

3:36 pm-9:00 pm

1 stop6h 24m

Lambert-St Louis

Tue 12/2

2:05 pm-9:35 pm

1 stop6h 30m

$263

PortlandMoline

PWM - MLI

PWMMLI

Portland

Sat 10/25

6:30 am-4:20 pm

2 stops10h 50m

Moline Quad-City

Tue 10/28

6:00 am-12:22 pm

1 stop5h 22m

$264

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 11/4

3:20 pm-9:16 pm

1 stop6h 56m

Chicago O'Hare Intl

Tue 11/11

5:31 pm-11:17 pm

1 stop4h 46m

$267

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 11/11

6:00 am-10:13 am

1 stop5h 13m

Chicago O'Hare Intl

Wed 11/12

6:45 am-12:08 pm

1 stop4h 23m

$267

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 11/11

12:48 pm-6:08 pm

1 stop6h 20m

Chicago Midway

Wed 11/12

9:34 am-4:07 pm

1 stop5h 33m

$267

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 10/15

7:09 am-12:22 pm

1 stop6h 13m

Chicago O'Hare Intl

Tue 10/21

1:35 pm-11:04 pm

1 stop8h 29m

$269

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 11/4

1:46 pm-8:37 pm

1 stop7h 51m

Chicago O'Hare Intl

Tue 11/11

11:19 am-11:54 pm

2 stops11h 35m

$272

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 11/12

2:30 pm-9:27 pm

1 stop7h 57m

Chicago O'Hare Intl

Wed 11/19

1:29 pm-11:54 pm

2 stops9h 25m

$272

PortlandChicago

PWM - MDW

PWMMDW

Portland

Tue 11/4

12:45 pm-6:25 pm

1 stop6h 40m

Chicago Midway

Tue 11/11

1:15 pm-11:19 pm

2 stops9h 04m

$272

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/28

Showing 1-10 of 59 results
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Best time to book a flight from Portland to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Portland 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 Portland to Illinois

What is the cheapest month to book a flight from Portland, Maine to Illinois?

Currently, August is the cheapest month in which you can book a flight from Portland, Maine to Illinois (average of $245). Flying from Portland, Maine to Illinois in March is currently the most expensive (average of $321). 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 PWM to IL?

Find hourly flight availability from Portland to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 29, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Portland, Maine to Illinois as you normally would.

Weekly flight availability from Portland, Maine to Illinois

Explore weekly flight availability from Portland to Illinois. 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 September 29, 2025.

The most flights from PWM to USIL are scheduled on a Monday (10 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (6 on average).

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated September 29, 2025.
Read through reviews of airlines operating flights from Portland to Illinois, 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
4,245 reviews

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,964 reviews
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,924 reviews
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Portland to Illinois. 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 from for flights from Portland to Illinois?

    Portland (PWM) is the airport you will fly out of if you book a flight from Portland to Illinois. It is only a 2.9 mi journey to Portland (PWM) from Portland’s city center.

  • How long is the flight from Portland, Maine to Illinois?

    For as low as $259, American Airlines can have you in Illinois from Portland, Maine in 6h 56m. The distance between Portland, Maine and Illinois is about 1036 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Portland, Maine to Illinois one-way?

    To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $132. Delta flights start at $134 while deals on Southwest start at $139 one-way.

  • What are the most popular routes from Portland, Maine to Illinois?

    The most popular route from Portland, Maine to Illinois is Portland - Chicago O'Hare Intl. You may also consider Portland - Chicago Midway or Portland - Lambert-St Louis.

  • What are the most reliable airlines from Portland, Maine to Illinois?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Portland, Maine to Illinois on time: American Airlines (76%), Republic Airways (74%), Air New Zealand (71%).

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

    Looking at all options, your cheapest flight can be booked for $115. While the most popular route (Portland - Chicago O'Hare Intl) can be booked for $247 on average, our data indicates $646 when flying from Portland, Maine to Illinois.

  • Can I find deals for flights from Portland to Illinois that include hotel bookings?

    Yes. In addition to deals on Portland to Illinois flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Illinois?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Illinois.

  • Can I find deals for business class flights from Portland to Illinois?

    Yes. Cheapflights offers flight deals from Portland to Illinois 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 Portland, Maine to Illinois?

    Currently, August is the cheapest month in which you can book a flight from Portland, Maine to Illinois (average of $245). Flying from Portland, Maine to Illinois in March is currently the most expensive (average of $321). 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.

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Alternative routes for Portland to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Portland to Illinois

Discover the top 4 airlines that operate flights from Portland to Illinois. 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 September 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$124Average$352FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$202Average$302FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$229Average$425FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$264Average$397FlexibilityNo cancel feeOn-time63%

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