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$90+ 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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ORD
May 19 — May 261
Mon 5/19
Mon 5/26
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 May 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Priceline
3 stars

Round-trip from

$209
(American Airlines)

One-way from

$90
(American Airlines)

Popular in

November

Cheapest in

July

Average price

$317

Good round-trip deal

$333 or less

Good one-way deal

$183 or less
Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Portland-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. 13% potential increase in price ($54 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 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 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 May 14, 2025.

This American Airlines deal was found by Cheapflights users on 5/12. 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 7/311:59 amPWM - ORD
Nonstop2h 53mAmerican Airlines
Mon 7/77:18 pmORD - PWM
Nonstop2h 34mAmerican Airlines
Deal found 5/12$209
This United Airlines deal was found by Cheapflights users on 5/13. 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 5/295:40 amPWM - ORD
1 stop4h 58mUnited Airlines
Tue 6/34:00 pmORD - PWM
1 stop6h 57mUnited Airlines
Deal found 5/13$214
This JetBlue deal was found by Cheapflights users on 5/13. 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.
Tue 6/176:10 amPWM - ORD
1 stop5h 03mJetBlue
Wed 7/96:00 amORD - PWM
1 stop6h 23mJetBlue
Deal found 5/13$220
This Delta deal was found by Cheapflights users on 5/13. 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 7/224:50 pmPWM - ORD
1 stop6h 37mDelta
Wed 7/309:25 amORD - PWM
1 stop5h 40mDelta
Deal found 5/13$229
This Southwest deal was found by Cheapflights users on 5/13. 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 8/2810:35 amPWM - MDW
Nonstop2h 30mSouthwest
Mon 9/15:40 amMDW - PWM
1 stop6h 35mSouthwest
Deal found 5/13$229
This Delta deal was found by Cheapflights users on 5/13. 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 7/212:49 pmPWM - MDW
1 stop6h 52mDelta
Sat 7/512:44 pmMDW - PWM
1 stop7h 53mDelta
Deal found 5/13$237
This Southwest deal was found by Cheapflights users on 5/13. 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 5/295:50 amPWM - ORD
2 stops7h 55mSouthwest
Tue 6/31:50 pmORD - PWM
1 stop7h 40mSouthwest
Deal found 5/13$250
This American Airlines deal was found by Cheapflights users on 5/13. 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 6/112:48 pmPWM - MLI
1 stop8h 21mAmerican Airlines
Tue 6/174:20 pmMLI - PWM
1 stop5h 24mAmerican Airlines
Deal found 5/13$259
This Booking.com deal was found by Cheapflights users on 5/13. 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.
Fri 5/169:30 pmPWM - STL
1 stop27h 36mFrontier
Sun 5/185:45 pmSTL - PWM
1 stop25h 55mFrontier
Deal found 5/13$281
This American Airlines deal was found by Cheapflights users on 5/12. 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 6/37:45 amPWM - STL
1 stop6h 07mAmerican Airlines
Tue 6/106:04 amSTL - PWM
1 stop5h 22mAmerican Airlines
Deal found 5/12$317
This Southwest deal was found by Cheapflights users on 5/12. 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 6/34:05 pmPWM - STL
1 stop6h 45mSouthwest
Tue 6/102:15 pmSTL - PWM
2 stops8h 10mSouthwest
Deal found 5/12$322
This Booking.com deal was found by Cheapflights users on 5/13. 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.
Fri 5/169:30 pmPWM - ORD
1 stop27h 02mFrontier
Sun 5/184:15 pmORD - PWM
1 stop27h 25mFrontier
Deal found 5/13$341

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 May 14, 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

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 7/3

11:59 am-1:52 pm

Nonstop2h 53m

Chicago O'Hare Intl

Mon 7/7

7:18 pm-10:52 pm

Nonstop2h 34m

$209

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 5/29

5:40 am-9:38 am

1 stop4h 58m

Chicago O'Hare Intl

Tue 6/3

4:00 pm-11:57 pm

1 stop6h 57m

$214

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 6/17

6:10 am-10:13 am

1 stop5h 03m

Chicago O'Hare Intl

Wed 7/9

6:00 am-1:23 pm

1 stop6h 23m

$220

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 7/22

6:53 pm-12:09 am

1 stop6h 16m

Chicago O'Hare Intl

Tue 7/29

5:59 pm-12:31 am

1 stop5h 32m

$229

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 8/28

10:35 am-12:05 pm

Nonstop2h 30m

Chicago Midway

Mon 9/1

5:40 am-1:15 pm

1 stop6h 35m

$229

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 7/2

12:49 pm-6:41 pm

1 stop6h 52m

Chicago Midway

Sat 7/5

12:44 pm-9:37 pm

1 stop7h 53m

$237

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 5/29

5:50 am-12:45 pm

2 stops7h 55m

Chicago O'Hare Intl

Tue 6/3

1:50 pm-10:30 pm

1 stop7h 40m

$250

PortlandMoline

PWM - MLI

PWMMLI

Portland

Wed 6/11

2:48 pm-10:09 pm

1 stop8h 21m

Moline Quad-City

Tue 6/17

4:20 pm-10:44 pm

1 stop5h 24m

$259

PortlandSt. Louis

PWM - STL

PWMSTL

Portland

Tue 6/3

5:24 pm-10:28 pm

1 stop6h 04m

Lambert-St Louis

Tue 6/10

2:49 pm-8:13 pm

1 stop4h 24m

$317

PortlandSt. Louis

PWM - STL

PWMSTL

Portland

Tue 6/3

4:05 pm-9:50 pm

1 stop6h 45m

Lambert-St Louis

Tue 6/10

2:15 pm-11:25 pm

2 stops8h 10m

$322

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/13

Showing 1-10 of 31 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 May 14, 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 May 14, 2025.

The most flights from PWM to USIL are scheduled on a Thursday (9 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (7 on average).

Rainfall in Illinois by month

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

In terms of precipitation, rainfall in Illinois ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Illinois when rainfall is around 1.7 in.

Temperature in Illinois by month

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

If weather is an important factor for your trip to Illinois, 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 73.4 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 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 May 14, 2025.
Get a feel of what it's like to fly with Southwest, Delta and United Airlines from Portland to Illinois by reading reviews from past customers. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,290 reviews

Comfort

8.0

Boarding

8.2

Overall

8.0

Crew

8.6

Food

7.1

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
4,290 reviews
Southwest
8.0
Very good
4,290 reviews

Comfort

8.0

Boarding

8.2

Overall

8.0

Crew

8.6

Food

7.1

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
7,949 reviews
Southwest
8.0
Very good
4,290 reviews

Comfort

8.0

Boarding

8.2

Overall

8.0

Crew

8.6

Food

7.1

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
8,726 reviews
Southwest
8.0
Very good
4,290 reviews

Comfort

8.0

Boarding

8.2

Overall

8.0

Crew

8.6

Food

7.1

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
4,290 reviews

Comfort

8.0

Boarding

8.2

Overall

8.0

Crew

8.6

Food

7.1

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
4,290 reviews

Comfort

8.0

Boarding

8.2

Overall

8.0

Crew

8.6

Food

7.1

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 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.

  • 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 $90. Southwest flights start at $90 while deals on United Airlines start at $100 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: Republic Airways (95%), Emirates (87%), United Airlines (83%).

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

    Looking at all options, your cheapest flight can be booked for $139. While the most popular route (Portland - Chicago O'Hare Intl) can be booked for $179 on average our data indicates $796 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 5 airlines flying from Portland to Illinois

Discover the top 5 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 May 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$114FlexibilityNo cancel feeOn-time62%
DeltaCheapest$124Average$353FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$158Average$315FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$199Average$448FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$264Average$371FlexibilityNo cancel feeOn-time63%

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