HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portland

$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.
CHI — PWM
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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 61 days in advance, depart on a Tuesday or Thursday 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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$251
(American Airlines)

One-way from

$90
(American Airlines)

Popular in

April

Cheapest in

February

Average price

$329

Good round-trip deal

$289 or less

Good one-way deal

$139 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. 4% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2025
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

Find 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 May 1, 2025.

This American Airlines deal was found by Cheapflights users on 4/30. 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.
Sat 6/217:01 amORD - PWM
1 stop7h 17mAmerican Airlines
Sat 6/286:01 pmPWM - ORD
1 stop6h 56mAmerican Airlines
Deal found 4/30$251
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/147:00 amORD - PWM
1 stop5h 50mDelta
Mon 5/195:30 amPWM - ORD
2 stops8h 11mDelta
Deal found 4/30$254
This Southwest deal was found by Cheapflights users on 4/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/278:15 amMDW - PWM
1 stop4h 10mSouthwest
Thu 5/292:30 pmPWM - MDW
2 stops6h 45mSouthwest
Deal found 4/30$254
This United Airlines deal was found by Cheapflights users on 4/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/214:50 pmORD - PWM
1 stop5h 11mUnited Airlines
Sun 8/246:00 amPWM - ORD
1 stop5h 38mUnited Airlines
Deal found 4/29$256
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/141:55 pmMDW - PWM
2 stops9h 04mDelta
Mon 5/195:30 amPWM - MDW
2 stops7h 58mDelta
Deal found 4/30$259
This Frontier deal was found by Cheapflights users on 4/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/149:08 amORD - PWM
1 stop8h 22mFrontier
Sat 6/217:25 pmPWM - ORD
1 stop12h 44mFrontier
Deal found 4/30$262
This JetBlue deal was found by Cheapflights users on 4/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/81:35 pmORD - PWM
1 stop7h 24mJetBlue
Sun 10/127:30 amPWM - ORD
1 stop6h 10mJetBlue
Deal found 4/30$275
This Southwest deal was found by Cheapflights users on 4/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/61:50 pmORD - PWM
1 stop9h 15mSouthwest
Tue 6/105:30 amPWM - ORD
2 stops8h 15mSouthwest
Deal found 4/30$280
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/2010:31 amORD - PWM
3 stops24h 26mMultiple Airlines
Sat 6/2812:58 pmPWM - ORD
1 stop8h 41mMultiple Airlines
Deal found 4/30$416

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 May 1, 2025.
Use the filters below to find and compare flights from Chicago to Portland that are best for you.

Fly from

Chicago

Fly to

Portland

Route

Depart

Return

Price

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 6/21

7:01 am-3:18 pm

1 stop7h 17m

Portland

Sat 6/28

6:01 pm-11:57 pm

1 stop6h 56m

$251

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 5/14

7:00 am-1:50 pm

1 stop5h 50m

Portland

Mon 5/19

5:30 am-12:41 pm

2 stops8h 11m

$254

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Tue 5/27

8:15 am-1:25 pm

1 stop4h 10m

Portland

Thu 5/29

2:30 pm-8:15 pm

2 stops6h 45m

$254

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 8/21

4:50 pm-11:01 pm

1 stop5h 11m

Portland

Sun 8/24

6:00 am-10:38 am

1 stop5h 38m

$256

ChicagoPortland

MDW - PWM

MDWPWM

Chicago Midway

Wed 5/14

1:55 pm-11:59 pm

2 stops9h 04m

Portland

Mon 5/19

5:30 am-12:28 pm

2 stops7h 58m

$259

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 6/14

9:08 am-6:30 pm

1 stop8h 22m

Portland

Sat 6/21

7:25 pm-7:09 am

1 stop12h 44m

$262

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 10/8

1:35 pm-9:59 pm

1 stop7h 24m

Portland

Sun 10/12

7:30 am-12:40 pm

1 stop6h 10m

$275

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 6/6

1:50 pm-12:05 am

1 stop9h 15m

Portland

Tue 6/10

5:30 am-12:45 pm

2 stops8h 15m

$280

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 6/20

10:31 am-11:57 am

3 stops24h 26m

Portland

Sat 6/28

12:58 pm-8:39 pm

1 stop8h 41m

$416

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 8/31

11:30 am-3:00 pm

Nonstop2h 30m

$90

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 21 results
1
2
3

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice 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 eDreams the most. eDreams 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

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 April 25, 2025.

The best time to book flights from Chicago to Portland, Maine is 61 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 May is currently the most expensive (average of $405). 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 May 1, 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 in the afternoon could potentially save you up to 46% 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 December 16, 2024.

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 May 1, 2025.

The most flights from CHI to PWM are scheduled on a Monday (6 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (3 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 May 1, 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.
Southwest
8.0
Very good
4,293 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,293 reviews
Southwest
8.0
Very good
4,293 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,293 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,293 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,923 reviews
Southwest
8.0
Very good
4,293 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,293 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 5 airlines. Portland is conveniently located just 2.9 mi from Portland’s city center.

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

    American Airlines, at $251, was found to be the cheapest airline from Chicago to Portland, Maine.Alternate airlines to your destination round-trip include Delta and Southwest. American Airlines is 28% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Chicago to Portland, Maine one-way?

    One-way options have recently been found by users for as low as $90 on American Airlines. Other airlines that offer cheap prices include United Airlines from $100 and JetBlue from $101 one-way.

  • 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 (84%), Air New Zealand (84%) or Republic Airways (74%) 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 $272, our data indicates the cheapest price to be $104. The most popular route (Chicago O'Hare Intl - Portland), is priced around $192.

  • 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, 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 May is currently the most expensive (average of $405). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
North Conway
Bath
Brunswick
Auburn
Conway
Lewiston

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Portland

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Boston flights
O'Hare Intl to Portland flights
Midway to Boston flights
O'Hare Intl to Bangor flights
St. Louis to Boston flights
Midway to Portland flights
St. Louis to Portland flights
St. Louis to Bangor flights
Midway to Bangor flights
Moline to Boston flights
Bloomington to Boston flights
Moline to Bangor flights
Peoria to Boston flights
Peoria to Portland flights
Moline to Portland flights
O'Hare Intl to Augusta flights
O'Hare Intl to Bar Harbor flights
O'Hare Intl to Rockland flights
Evansville to Boston flights
Dubuque to Boston flights
Springfield to Boston flights
Evansville to Portland flights
Decatur to Boston flights
Champaign to Boston flights
Peoria to Bangor flights
Springfield to Portland flights
Bloomington to Portland flights
Bloomington to Bangor flights
Champaign to Portland flights
Dubuque to Portland flights
Champaign to Bangor flights
St. Louis to Presque Isle flights
Evansville to Bangor flights

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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$87FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$178Average$330FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$191Average$406FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$212Average$386FlexibilityNo cancel feeOn-time69%
DeltaCheapest$228Average$479FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
Privacy Preferences©2025 Cheapflights