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$55+ 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 2/20. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ORD
Feb 3 — Feb 101
Mon 2/3
Mon 2/10
1 adult, Economy
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Cheap flight deals from Portland to Illinois

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) to Illinois (USIL). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$238
(Southwest)

One-way from

$66
(Booking.com)

Popular in

April

Cheapest in

September

Average price

$351

Good round-trip deal

$436 or less

Good one-way deal

$225 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. 17% potential increase in price ($82 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in January 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 January 29, 2025.

This Southwest deal was found by Cheapflights users on 1/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/272:50 pmPWM - MDW
2 stops7h 45mSouthwest
Thu 3/64:45 pmMDW - PWM
1 stop6h 20mSouthwest
Deal found 1/28$238
This Delta deal was found by Cheapflights users on 1/28. 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.
Fri 3/75:25 pmPWM - ORD
1 stop6h 11mDelta
Sun 3/96:45 amORD - PWM
1 stop4h 31mDelta
Deal found 1/28$239
This Frontier deal was found by Cheapflights users on 1/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/110:23 amPWM - ORD
1 stop10h 16mFrontier
Mon 3/35:10 amORD - PWM
1 stop13h 25mFrontier
Deal found 1/28$240
This Delta deal was found by Cheapflights users on 1/28. 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.
Sat 3/227:00 amPWM - MDW
1 stop6h 32mDelta
Wed 3/266:42 pmMDW - PWM
1 stop3h 32mDelta
Deal found 1/28$254
This Southwest deal was found by Cheapflights users on 1/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/105:30 pmPWM - ORD
1 stop5h 00mSouthwest
Sat 3/154:00 pmORD - PWM
1 stop7h 15mSouthwest
Deal found 1/28$258
This Booking.com deal was found by Cheapflights users on 1/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/29:29 pmPWM - STL
1 stop27h 32mFrontier
Sun 5/115:47 pmSTL - PWM
1 stop25h 42mFrontier
Deal found 1/28$260
This American Airlines deal was found by Cheapflights users on 1/28. 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.
Thu 5/16:00 amPWM - ORD
1 stop6h 05mAmerican Airlines
Mon 5/58:00 amORD - PWM
Nonstop2h 34mAmerican Airlines
Deal found 1/28$262
This JetBlue deal was found by Cheapflights users on 1/28. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/146:10 amPWM - ORD
1 stop7h 17mJetBlue
Tue 4/221:22 pmORD - PWM
1 stop8h 38mJetBlue
Deal found 1/28$273
This FlightHub deal was found by Cheapflights users on 1/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/126:48 pmPWM - MDW
1 stop28h 58mFrontier
Sat 2/1512:43 pmMDW - PWM
1 stop19h 35mFrontier
Deal found 1/28$273
This Cheapflightsfares deal was found by Cheapflights users on 1/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/2712:32 pmPWM - ORD
1 stop7h 39mSun Country Air
Sun 6/298:10 pmORD - PWM
1 stop14h 25mSun Country Air
Deal found 1/28$280
This eDestinos deal was found by Cheapflights users on 1/28. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2710:08 amPWM - ORD
2 stops53h 01mMultiple Airlines
Thu 3/611:55 amORD - PWM
2 stops28h 15mMultiple Airlines
Deal found 1/28$290
This United Airlines deal was found by Cheapflights users on 1/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/124:10 pmPWM - ORD
Nonstop3h 14mUnited Airlines
Sun 2/1612:54 pmORD - PWM
Nonstop2h 18mUnited Airlines
Deal found 1/27$299

Find flights from Portland to Illinois within your budget

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 January 29, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 4/9

2:20 pm-7:10 pm

2 stops5h 50m

Chicago Midway

Fri 4/11

5:45 am-1:40 pm

1 stop6h 55m

$238

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 3/7

5:25 pm-10:36 pm

1 stop6h 11m

Chicago O'Hare Intl

Sun 3/9

6:45 am-12:16 pm

1 stop4h 31m

$239

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 3/1

10:23 am-7:39 pm

1 stop10h 16m

Chicago O'Hare Intl

Mon 3/3

5:10 am-7:35 pm

1 stop13h 25m

$240

PortlandChicago

PWM - MDW

PWMMDW

Portland

Wed 4/2

6:15 am-12:36 pm

2 stops7h 21m

Chicago Midway

Sat 4/5

1:12 pm-11:59 pm

2 stops9h 47m

$249

PortlandChicago

PWM - ORD

PWMORD

Portland

Mon 3/10

5:30 pm-9:30 pm

1 stop5h 00m

Chicago O'Hare Intl

Sat 3/15

4:00 pm-12:15 am

1 stop7h 15m

$258

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 5/1

6:00 am-11:05 am

1 stop6h 05m

Chicago O'Hare Intl

Mon 5/5

8:00 am-11:34 am

Nonstop2h 34m

$262

PortlandChicago

PWM - ORD

PWMORD

Portland

Mon 4/14

6:10 am-12:27 pm

1 stop7h 17m

Chicago O'Hare Intl

Tue 4/22

1:22 pm-11:00 pm

1 stop8h 38m

$273

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 6/27

12:32 pm-7:11 pm

1 stop7h 39m

Chicago O'Hare Intl

Sun 6/29

8:10 pm-11:35 am

1 stop14h 25m

$280

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 2/27

10:08 am-2:09 pm

2 stops53h 01m

Chicago O'Hare Intl

Thu 3/6

11:55 am-5:10 pm

2 stops28h 15m

$290

PortlandSt. Louis

PWM - STL

PWMSTL

Portland

Sat 3/1

10:23 am-11:43 pm

1 stop14h 20m

Lambert-St Louis

Mon 3/3

5:20 pm-9:18 am

1 stop14h 58m

$290

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

Showing 1-10 of 28 results
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2
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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.

Travel insights for flights from Portland to Illinois

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

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 $325). 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 January 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 January 29, 2025.

The most flights from PWM to USIL are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 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 January 29, 2025.
Get a feel of what it's like to fly with Southwest, Delta and JetBlue 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
8.1
Very good
4,587 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,587 reviews
Southwest
8.1
Very good
4,587 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,456 reviews
Southwest
8.1
Very good
4,587 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,156 reviews
Southwest
8.1
Very good
4,587 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,916 reviews
Southwest
8.1
Very good
4,587 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,587 reviews

Boarding

8.2

Entertainment

7.7

Comfort

8.1

Crew

8.7

Food

7.1

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 Frontier, which is currently one of the cheapest options available, starting at $66. JetBlue flights start at $82 while deals on American Airlines start at $105 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: Air New Zealand (90%), Republic Airways (89%), United Airlines (88%).

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

    Looking at all options, your cheapest flight can be booked for $183. While the most popular route (Portland - Chicago O'Hare Intl) can be booked for $175 on average our data indicates $900 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 $325). 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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Alternative routes for Portland to Illinois

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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 January 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$110FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$158Average$411FlexibilityNo cancel feeOn-time71%
DeltaCheapest$201Average$398FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$205Average$409FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$281Average$390FlexibilityNo cancel feeOn-time63%
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