$90+ Cheap flights from Chicago (CHI) 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 Chicago 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.Cheapflights Tip: The best prices from Chicago to Portland are usually found in February or March, booked 64 days in advance, depart on a Tuesday or Sunday and return on a Thursday
Cheap flight deals from Chicago to Portland
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Portland (PWM). 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 June 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 Chicago to Portland
Cheapest flights from Chicago to PortlandExplore the most affordable flight options available from Chicago to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.
Explore the most affordable flight options available from Chicago to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 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 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.
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This FlightHub 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 FlightHub 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 Chicago 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 June 12, 2025.
Use the filters below to find and compare flights from Chicago to Portland that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Sun 9/7
6:45 am-1:22 pm
1 stop5h 37m
Portland
Fri 9/12
2:17 pm-8:50 pm
1 stop7h 33m
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Tue 7/8
8:00 am-8:24 pm
1 stop11h 24m
Portland
Tue 7/15
2:34 pm-9:31 pm
1 stop7h 57m
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Tue 7/1
4:46 pm-11:14 pm
1 stop5h 28m
Portland
Fri 7/4
5:35 am-11:43 am
1 stop7h 08m
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Wed 8/13
5:45 am-4:10 pm
2 stops9h 25m
Portland
Wed 8/20
6:31 am-9:53 pm
1 stop16h 22m
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Wed 6/25
1:50 pm-11:25 pm
1 stop8h 35m
Portland
Mon 6/30
5:40 am-1:05 pm
1 stop8h 25m
ChicagoPortland
MDW - PWM
MDWPWM
Chicago Midway
Wed 9/3
4:25 pm-12:03 am
1 stop6h 38m
Portland
Sat 9/6
1:34 pm-9:12 pm
1 stop8h 38m
ChicagoPortland
MDW - PWM
MDWPWM
Chicago Midway
Tue 8/19
2:55 pm-10:25 pm
1 stop6h 30m
Portland
Sat 8/23
4:50 pm-6:25 pm
Nonstop2h 35m
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Sun 7/6
6:45 am-11:17 am
1 stop27h 32m
Portland
Fri 7/11
11:16 am-5:21 pm
1 stop7h 05m
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Thu 6/26
10:43 am-11:45 am
2 stops24h 02m
Portland
Mon 6/30
12:16 pm-5:15 pm
1 stop5h 59m
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Sat 8/2
9:08 am-6:13 pm
1 stop8h 05m
Portland
Sat 8/9
6:58 pm-3:43 pm
1 stop21h 45m
Best time to book a flight from Chicago to Portland
Have a flexible travel schedule? Discover the best time to fly to Portland from Chicago with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Portland
How far ahead should I book a flight from Chicago to Portland, Maine?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to Portland. Price data was last updated on June 9, 2025.
The best time to book flights from Chicago to Portland, Maine is 64 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Chicago to Portland, Maine?
Currently, January is the cheapest month in which you can book a flight from Chicago to Portland, Maine (average of $296). Flying from Chicago 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 CHI to PWM?
Find hourly flight availability from Chicago 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 June 12, 2025.
One of the essential ways to save on airfare from Chicago to Portland, Maine is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 24% on airfare.
What is the cheapest day to fly from Chicago to Portland, Maine?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Portland. Price data was last updated on June 8, 2025.
Travelers seeking maximum savings on their Chicago to Portland, Maine flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago to Portland, Maine
Explore weekly flight availability from Chicago 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 June 12, 2025.
The most flights from CHI to PWM are scheduled on a Monday (9 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 June 12, 2025.
Read reviews from past customers who have flown Southwest, Delta and United Airlines from Chicago to Portland. Reviews also offer insight into each airline's 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 Chicago 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 Chicago to Portland
See prices for flight routes from nearby airports that may be better suited for you.
Top 5 airlines flying from Chicago to Portland
Discover the top 5 airlines that operate flights from Chicago 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 June 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$331 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$191 | Average$401 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$213 | Average$385 | FlexibilityNo cancel fee | On-time69% |