$90+ 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Illinois to Portland with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.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 junio 12, 2025.
Round-trip from | $233 (JetBlue) |
|---|---|
One-way from | $90 (United Airlines) |
Popular in | December |
Cheapest in | February |
Average price | $340 |
Good round-trip deal | $259 or less |
Good one-way deal | $153 or less |
Find flight deals from Illinois to Portland
Cheapest flights from Illinois to PortlandExplore 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 junio 12, 2025.
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 junio 12, 2025.
This JetBlue deal was found by Cheapflights users on 6/9. 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.
This American Airlines deal was found by Cheapflights users on 6/12. 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.
This United Airlines deal was found by Cheapflights users on 6/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Southwest deal was found by Cheapflights users on 6/10. 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.
This Delta deal was found by Cheapflights users on 6/10. 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.
This Southwest deal was found by Cheapflights users on 6/10. 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.
This Delta deal was found by Cheapflights users on 6/10. 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.
This American Airlines deal was found by Cheapflights users on 6/11. 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.
This American Airlines deal was found by Cheapflights users on 6/11. 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.
This Booking.com deal was found by Cheapflights users on 6/10. 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.
This United Airlines deal was found by Cheapflights users on 6/11. 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.
This Sun Country Air deal was found by Cheapflights users on 6/10. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Cheapflights Fare Finder
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 junio 12, 2025.
Use the filters below to find and compare flights from Illinois to Portland that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
dom. 9/7
6:45 am-1:22 pm
1 stop5h 37m
Portland
vie. 9/12
2:17 pm-8:50 pm
1 stop7h 33m
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
mar. 7/8
8:00 am-8:24 pm
1 stop11h 24m
Portland
mar. 7/15
2:34 pm-9:31 pm
1 stop7h 57m
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
mar. 7/1
4:46 pm-11:14 pm
1 stop5h 28m
Portland
vie. 7/4
5:35 am-11:43 am
1 stop7h 08m
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
mié. 8/13
5:45 am-4:10 pm
2 stops9h 25m
Portland
mié. 8/20
6:31 am-9:53 pm
1 stop16h 22m
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
mié. 6/25
1:50 pm-11:25 pm
1 stop8h 35m
Portland
lun. 6/30
5:40 am-1:05 pm
1 stop8h 25m
ChicagoPortland
MDW - PWM
MDWPWM
Chicago Midway
mié. 9/3
4:25 pm-12:03 am
1 stop6h 38m
Portland
sáb. 9/6
1:34 pm-9:12 pm
1 stop8h 38m
ChicagoPortland
MDW - PWM
MDWPWM
Chicago Midway
mar. 8/19
2:55 pm-10:25 pm
1 stop6h 30m
Portland
sáb. 8/23
4:50 pm-6:25 pm
Nonstop2h 35m
MolinePortland
MLI - PWM
MLIPWM
Moline Quad-City
vie. 9/5
8:19 am-4:17 pm
1 stop6h 58m
Portland
vie. 9/12
5:10 pm-10:25 pm
1 stop6h 15m
PeoriaPortland
PIA - PWM
PIAPWM
Greater Peoria
jue. 9/11
6:30 pm-12:09 am
1 stop4h 39m
Portland
mar. 9/16
6:00 am-10:08 am
1 stop5h 08m
St. LouisPortland
STL - PWM
STLPWM
Lambert-St Louis
vie. 8/8
5:40 pm-6:13 pm
1 stop23h 33m
Portland
sáb. 8/16
6:58 pm-11:47 pm
1 stop29h 49m
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.
Cheapflights Insights
Everything you need to know about your flight from Illinois to Portland
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 July is currently the most expensive (average of $394). 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 junio 12, 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.
Weekly flight availability from Illinois to Portland, Maine
Explore weekly flight availability from Illinois to Portland. 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 junio 12, 2025.
The most flights from USIL to PWM are scheduled on a Monday (8 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).
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 junio 12, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and United Airlines 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.
Overall
Entertainment
Comfort
Food
Boarding
Crew
Reviews
John,May 2025
PVD - BNA
Overall
Entertainment
Comfort
Food
Boarding
Crew
Reviews
John,May 2025
PVD - BNA
Overall
Entertainment
Comfort
Food
Boarding
Crew
Reviews
John,May 2025
PVD - BNA
Overall
Entertainment
Comfort
Food
Boarding
Crew
Reviews
John,May 2025
PVD - BNA
Overall
Entertainment
Comfort
Food
Boarding
Crew
Reviews
John,May 2025
PVD - BNA
Overall
Entertainment
Comfort
Food
Boarding
Crew
Reviews
John,May 2025
PVD - BNA
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.
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Alternative routes for Illinois to Portland
See prices for flight routes from nearby airports that may be better suited for you.
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 junio 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$57 | Average$88 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$163 | Average$479 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$176 | Average$418 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$191 | Average$401 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$213 | Average$466 | FlexibilityNo cancel fee | On-time69% |