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Portland

$145+ 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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PWM
Aug 31 — Sep 71
Mon 8/31
Mon 9/7
1 adult, Economy
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Find cheap flights from Chicago to Portland with Cheapflights

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Cheapflights Tip: The best prices from Chicago to Portland are usually found in May or April, booked 47 days in advance, depart on a Saturday or Wednesday and return on a Wednesday

Cheap flight deals from Chicago to Portland

Cheapest flights from Chicago to Portland
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 August 1, 2026.

This United Airlines deal was found by Cheapflights users on 7/30. 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 9/35:50 pm
ORD
-
PWM
Nonstop2h 33m
United Airlines
Tue 9/86:00 am
PWM
-
ORD
Nonstop2h 57m
United Airlines
Deal found 7/30$279
This United Airlines deal was found by Cheapflights users on 7/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/16:00 pm
ORD
-
PWM
Nonstop2h 27m
United Airlines
Sat 12/129:45 am
PWM
-
ORD
Nonstop2h 57m
United Airlines
Deal found 7/28$281
This American Airlines deal was found by Cheapflights users on 7/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/175:54 pm
ORD
-
PWM
1 stop5h 05m
American Airlines
Mon 9/214:41 pm
PWM
-
ORD
1 stop7h 34m
American Airlines
Deal found 7/27$282
This Southwest deal was found by Cheapflights users on 7/31. 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.
Sat 8/295:55 am
MDW
-
PWM
1 stop4h 50m
Southwest
Sat 9/510:30 am
PWM
-
MDW
1 stop7h 10m
Southwest
Deal found 7/31$282
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Mon 9/148:14 am
ORD
-
PWM
1 stop6h 37m
American Airlines
Mon 9/216:00 am
PWM
-
ORD
1 stop7h 50m
American Airlines
Deal found 7/30$283
This United Airlines deal was found by Cheapflights users on 7/30. 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 9/306:59 am
ORD
-
PWM
Nonstop2h 41m
United Airlines
Mon 10/56:00 am
PWM
-
ORD
Nonstop2h 57m
United Airlines
Deal found 7/30$284
This CheapOair deal was found by Cheapflights users on 7/31. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:00 am
ORD
-
PWM
1 stop6h 45m
JetBlue
Sat 8/292:40 pm
PWM
-
ORD
1 stop8h 18m
JetBlue
Deal found 7/31$286
This Southwest deal was found by Cheapflights users on 7/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/265:55 am
MDW
-
PWM
1 stop4h 50m
Southwest
Thu 10/16:30 am
PWM
-
MDW
Nonstop2h 35m
Southwest
Deal found 7/27$286
This Delta deal was found by Cheapflights users on 7/31. 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 8/299:30 am
ORD
-
PWM
1 stop5h 28m
Delta
Sat 9/56:00 am
PWM
-
ORD
2 stops11h 51m
Delta
Deal found 7/31$287
This Southwest deal was found by Cheapflights users on 7/31. 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 9/76:10 pm
MDW
-
PWM
Nonstop2h 25m
Southwest
Thu 9/107:40 am
PWM
-
MDW
Nonstop2h 30m
Southwest
Deal found 7/31$289
This American Airlines deal was found by Cheapflights users on 7/31. 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 9/161:10 pm
ORD
-
PWM
Nonstop2h 44m
American Airlines
Mon 9/215:38 pm
PWM
-
ORD
Nonstop3h 21m
American Airlines
Deal found 7/31$291
This Delta deal was found by Cheapflights users on 7/29. 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 8/221:50 pm
ORD
-
PWM
1 stop6h 41m
Delta
Thu 8/276:30 am
PWM
-
ORD
2 stops11h 21m
Delta
Deal found 7/29$292

Find 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 August 1, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$279
(United Airlines)

One-way from

$145
(American Airlines)

Popular in

July

Cheapest in

May

Average price

$377

Good round-trip deal

$336 or less

Good one-way deal

$162 or less
Provider with most accurate pricing for Chicago (CHI)-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Portland flights.
Search Deals
From Chicago (CHI) to Portland
Search Deals
One-way flight from Chicago (CHI) to Portland
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 ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Portland.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Portland.
Search 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 August 1, 2026.
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

Cheapest round-trip

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Sat 9/26

5:55 am-11:45 am

1 stop4h 50m

Portland

Thu 10/1

6:30 am-8:05 am

Nonstop2h 35m

$286

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 8/22

5:50 pm-9:23 pm

Nonstop2h 33m

Portland

Tue 8/25

6:00 am-7:57 am

Nonstop2h 57m

$315

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 8/22

5:50 pm-9:23 pm

Nonstop2h 33m

Portland

Mon 8/24

6:03 am-8:00 am

Nonstop2h 57m

$315

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 9/15

6:50 pm-10:10 pm

Nonstop2h 20m

Portland

Sat 9/19

5:40 am-2:40 pm

2 stops10h 00m

$318

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 8/22

1:50 pm-12:59 am

2 stops10h 09m

Portland

Thu 8/27

6:30 am-4:51 pm

2 stops11h 21m

$319

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 9/29

5:30 am-4:49 pm

2 stops10h 19m

Portland

Tue 10/6

6:01 am-4:32 pm

2 stops11h 31m

$319

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 9/11

1:55 pm-11:29 pm

2 stops8h 34m

Portland

Fri 9/18

4:20 pm-9:37 pm

1 stop6h 17m

$325

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Mon 8/24

5:30 am-4:50 pm

2 stops10h 20m

Portland

Thu 8/27

6:30 am-4:51 pm

2 stops11h 21m

$357

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 10/29

1:56 pm-11:35 pm

2 stops8h 39m

Portland

Sun 11/1

2:09 pm-7:11 pm

1 stop6h 02m

$358

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Thu 8/13

5:25 pm-10:25 pm

1 stop4h 00m

Portland

Wed 8/19

7:45 am-9:20 am

Nonstop2h 35m

$366

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 40 resultsSorted by cheapest first
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Compare providers for flights from Chicago to Portland

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Portland in August.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Portland, Maine flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Portland, Maine flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Portland, Maine flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Portland, Maine flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Portland, Maine flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.
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 Chicago to Portland

What is the cheapest month to book a flight from Chicago to Portland, Maine?

Currently, March is the cheapest month in which you can book a flight from Chicago to Portland, Maine (average of $313). Flying from Chicago to Portland, Maine in July is currently the most expensive (average of $439). 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 August 1, 2026.

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 in the afternoon could potentially save you up to 34% on airfare.

How much does it cost to fly round-trip from Chicago to Portland, Maine?

Airfare is below average for this route at the moment.
Chicago to Portland, Maine flights typically cost between $308 and $452 in September.
The cheapest round-trip price found within the last 5 days was $279 on United Airlines (Sep 3-Sep 8).

How often are flights from Chicago to Portland delayed?

About 19% of weekly flights between Chicago and Portland have experienced delays in the past year, with the average delay time being 139 minutes.

What is the most punctual flight time for Chicago to Portland flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Tuesday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Portland flights?

Over the last year, Southwest have had the lowest number of delays on this route, with just 13% of flights being delayed.

How far ahead should I book a flight from Chicago to Portland, Maine?

The best time to book flights from Chicago to Portland, Maine is 46 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 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 July 4, 2026.

Travelers seeking maximum savings on their Chicago to Portland, Maine flight should consider departing on Sunday afternoons 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.

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 August 1, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines from Chicago to Portland by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,229 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,229 reviews
Southwest
8.0
Very good
4,229 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
United Airlines
7.4
Good
10,062 reviews
Southwest
8.0
Very good
4,229 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
American Airlines
7.1
Good
11,845 reviews
Southwest
8.0
Very good
4,229 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

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.

  • What airport do you fly into for flights to Portland from Chicago?

    Most people fly into Portland (PWM) if they book a flight to Portland from Chicago. On average, Portland has 4 inbound flights from Chicago per day from 2 airlines. Portland is conveniently located just 2.9 mi from Portland’s city center.

  • How long is the flight from Chicago to Portland, Maine?

    There are many flights that can get you from Chicago to Portland, Maine in 2h 33m. Fly via Southwest, United Airlines, or Delta to get the fastest option. There are 897 mi between Chicago and Portland, Maine. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago to Portland, Maine round-trip?

    American Airlines, at $229, was found to be the cheapest airline from Chicago to Portland, Maine. An alternate airline flying to your destination would be United Airlines. American Airlines is 36% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the most reliable airlines from Chicago to Portland, Maine?

    No one likes to see their flight delayed. When booking a flight from Chicago to Portland, Maine consider choosing SkyWest Airlines (85%), Republic Airways (80%) or American Airlines (78%) as they are the most reliable in getting you off to your destination on time.

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

    Looking for the cheapest flight from Chicago to Portland, Maine? While on average our users pay $407, our data indicates the cheapest price to be $134. The most popular route (Chicago O'Hare Intl - Portland), is priced around $235.

  • Can I find deals for flights from Chicago to Portland that include hotel bookings?

    Yes. In addition to deals on Chicago to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Portland.

  • Can I find deals for business class flights from Chicago to Portland?

    Yes. Cheapflights offers flight deals from Chicago to Portland 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 Chicago to Portland, Maine?

    Currently, March is the cheapest month in which you can book a flight from Chicago to Portland, Maine (average of $313). Flying from Chicago to Portland, Maine in July is currently the most expensive (average of $439). 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

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
North Conway
Lewiston
Brunswick
Conway

Browse thousands of different options on Cheapflights for your next trip

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Top 2 airlines flying from Chicago to Portland

Discover the top 2 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 August 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$229Average$369FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$230Average$369FlexibilityNo cancel feeOn-time69%

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