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Illinois

$96+ 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 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ORD
Dec 16 — Dec 231
Tue 12/16
Tue 12/23
1 adult, Economy
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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 November 16, 2025.

This Delta deal was found by Cheapflights users on 11/15. 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 11/244:40 pmPWM - ORD
1 stop5h 04mDelta
Fri 11/281:29 pmORD - PWM
2 stops7h 50mDelta
Deal found 11/15$284
This Delta deal was found by Cheapflights users on 11/14. 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.
Sun 12/76:08 amPWM - MDW
1 stop6h 47mDelta
Sun 12/141:14 pmMDW - PWM
2 stops9h 07mDelta
Deal found 11/14$284
This United Airlines deal was found by Cheapflights users on 11/15. 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 12/116:00 amPWM - ORD
1 stop5h 44mUnited Airlines
Sat 12/135:50 pmORD - PWM
Nonstop2h 27mUnited Airlines
Deal found 11/15$289
This Delta deal was found by Cheapflights users on 11/14. 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 12/62:34 pmPWM - MDW
2 stops10h 13mDelta
Sun 12/141:14 pmMDW - PWM
2 stops9h 07mDelta
Deal found 11/14$289
This United Airlines deal was found by Cheapflights users on 11/14. 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.
Mon 11/245:00 pmPWM - ORD
Nonstop2h 55mUnited Airlines
Fri 11/2810:53 amORD - PWM
Nonstop2h 19mUnited Airlines
Deal found 11/14$299
This Kiwi.com deal was found by Cheapflights users on 11/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/89:46 amPWM - ORD
1 stop13h 02mMultiple Airlines
Mon 12/155:17 pmORD - PWM
2 stops40h 19mMultiple Airlines
Deal found 11/15$300
This Delta deal was found by Cheapflights users on 11/15. 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.
Thu 12/116:08 amPWM - ORD
2 stops11h 14mDelta
Sun 12/146:45 amORD - PWM
1 stop4h 28mDelta
Deal found 11/15$304
This Delta deal was found by Cheapflights users on 11/14. 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 11/246:00 amPWM - MDW
2 stops11h 39mDelta
Fri 11/286:00 amMDW - PWM
1 stop5h 30mDelta
Deal found 11/14$304
This United Airlines deal was found by Cheapflights users on 11/14. 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.
Sat 11/229:45 amPWM - ORD
Nonstop3h 10mUnited Airlines
Tue 11/2510:53 amORD - PWM
Nonstop2h 19mUnited Airlines
Deal found 11/14$309
This Kiwi.com deal was found by Cheapflights users on 11/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/129:46 amPWM - MDW
1 stop13h 53mMultiple Airlines
Sun 12/146:37 pmMDW - PWM
1 stop13h 29mMultiple Airlines
Deal found 11/15$311
This Southwest deal was found by Cheapflights users on 11/15. 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 12/115:30 amPWM - MDW
2 stops8h 30mSouthwest
Sun 12/146:45 amMDW - PWM
2 stops9h 05mSouthwest
Deal found 11/15$314
This United Airlines deal was found by Cheapflights users on 11/13. 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.
Fri 12/54:25 pmPWM - ORD
Nonstop3h 10mUnited Airlines
Sun 12/78:50 amORD - PWM
1 stop4h 29mUnited Airlines
Deal found 11/13$324

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 November 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$284
(Delta)

One-way from

$96
(Priceline)

Popular in

December

Cheapest in

September

Average price

$391

Good round-trip deal

$337 or less

Good one-way deal

$189 or less
Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Chicago (CHI) flights.
Search Deals
From Portland to Illinois
Search Deals
One-way flight from Portland to Illinois
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Portland to Illinois.
Search Deals
Price to beat on a one-way flight from Portland to Illinois.
Search Deals

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 November 16, 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 2/26

5:31 am-1:39 pm

1 stop9h 08m

Chicago O'Hare Intl

Mon 3/2

2:03 pm-11:22 pm

2 stops8h 19m

$284

PortlandChicago

PWM - ORD

PWMORD

Portland

Mon 12/8

2:34 pm-12:01 am

2 stops10h 27m

Chicago O'Hare Intl

Sat 12/13

6:45 am-12:13 pm

1 stop4h 28m

$284

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 1/22

5:30 am-11:59 am

1 stop7h 29m

Chicago Midway

Sun 1/25

1:26 pm-11:22 pm

2 stops8h 56m

$284

PortlandChicago

PWM - ORD

PWMORD

Portland

Mon 1/12

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

Wed 1/14

11:00 am-2:39 pm

Nonstop2h 39m

$287

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 12/11

6:00 am-10:44 am

1 stop5h 44m

Chicago O'Hare Intl

Sat 12/13

5:50 pm-9:17 pm

Nonstop2h 27m

$289

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 2/26

5:45 am-7:57 am

Nonstop3h 12m

Chicago O'Hare Intl

Mon 3/2

2:30 pm-8:28 pm

1 stop4h 58m

$289

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 12/9

6:08 am-4:57 pm

2 stops11h 49m

Chicago O'Hare Intl

Sat 12/13

6:00 am-4:00 pm

2 stops9h 00m

$289

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 12/5

2:34 pm-12:01 am

2 stops10h 27m

Chicago O'Hare Intl

Mon 12/8

1:01 pm-11:21 pm

2 stops9h 20m

$289

PortlandChicago

PWM - MDW

PWMMDW

Portland

Thu 2/26

6:00 am-12:48 pm

2 stops7h 48m

Chicago Midway

Mon 3/2

12:46 pm-11:22 pm

2 stops9h 36m

$289

PortlandChicago

PWM - MDW

PWMMDW

Portland

Sat 12/6

2:34 pm-11:47 pm

2 stops10h 13m

Chicago Midway

Sun 12/14

1:14 pm-11:21 pm

2 stops9h 07m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/14

Showing 1-10 of 53 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, April is the cheapest month in which you can book a flight from Portland, Maine to Illinois (average of $89). Flying from Portland, Maine to Illinois in January is currently the most expensive (average of $123). 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 November 16, 2025.

It’s optimal to fly from Portland, Maine to Illinois in the evening. By choosing this option you can save up to 39% on the cost of your flight, compared to a flight in the morning.

What is the cheapest day to fly from Portland, Maine to Illinois?

Use this chart to determine the cheapest time to fly round-trip from Portland to Illinois. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Portland, Maine to Illinois flight should consider departing on Saturday evenings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 November 16, 2025.

The most flights from PWM to USIL are scheduled on a Thursday (5 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 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 November 16, 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
4,246 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

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
7.9
Good
8,010 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

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
9,017 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

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
11,051 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

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 $287, Delta can have you in Illinois from Portland, Maine in 3h 08m. The distance between Portland, Maine and Illinois is about 897 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 United Airlines, which is currently one of the cheapest options available, starting at $105. Delta flights start at $115 while deals on Southwest start at $115 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 (91%), United Airlines (80%), 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 $125. While the most popular route (Portland - Chicago O'Hare Intl) can be booked for $209 on average, our data indicates $964 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, April is the cheapest month in which you can book a flight from Portland, Maine to Illinois (average of $89). Flying from Portland, Maine to Illinois in January is currently the most expensive (average of $123). 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

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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 November 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$124Average$352FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$203Average$304FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$229Average$423FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$246Average$390FlexibilityNo cancel feeOn-time63%

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