HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portland

$90+ Cheap flights from O'Hare Intl (ORD) 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 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
Apr 20 — Apr 271
Sun 4/20
Sun 4/27
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from O'Hare Intl 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 O'Hare Intl to Portland are usually found in July or August, booked 79 days in advance, depart on a Tuesday or Thursday and return on a Thursday

Cheap flight deals from O'Hare Intl to Portland

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) 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 April 15, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$237
(United Airlines)

One-way from

$90
(American Airlines)

Popular in

November

Cheapest in

July

Average price

$366

Good round-trip deal

$286 or less

Good one-way deal

$139 or less
Provider with most accurate pricing for Chicago O'Hare Intl-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Portland flights.
Search Deals
From Chicago O'Hare Intl to Portland
Search Deals
One-way flight from Chicago O'Hare Intl to Portland
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($77 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals
Price to beat on a round-trip flight from Chicago O'Hare Intl to Portland.
Search Deals
Price to beat on a one-way flight from Chicago O'Hare Intl to Portland.
Search Deals

Find flight deals from O'Hare Intl to Portland

Cheapest flights from O'Hare Intl to Portland
Explore the most affordable flight options available from O'Hare Intl to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 15, 2025.

This United Airlines deal was found by Cheapflights users on 4/14. 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 6/39:00 amORD - PWM
1 stop7h 43mUnited Airlines
Wed 6/116:00 amPWM - ORD
Nonstop2h 53mUnited Airlines
Deal found 4/14$237
This Delta deal was found by Cheapflights users on 4/14. 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 8/910:35 amORD - PWM
2 stops10h 09mDelta
Sat 8/166:30 amPWM - ORD
2 stops8h 50mDelta
Deal found 4/14$239
This CheapOair deal was found by Cheapflights users on 4/14. 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.
Fri 5/94:15 pmORD - PWM
1 stop25h 11mFrontier
Sun 5/118:23 pmPWM - ORD
1 stop28h 09mFrontier
Deal found 4/14$240
This JetBlue deal was found by Cheapflights users on 4/14. 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.
Fri 5/26:20 amORD - PWM
1 stop7h 05mJetBlue
Mon 5/53:20 pmPWM - ORD
1 stop8h 02mJetBlue
Deal found 4/14$250
This American Airlines deal was found by Cheapflights users on 4/14. 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 8/277:12 pmORD - PWM
Nonstop2h 34mAmerican Airlines
Mon 9/16:00 amPWM - ORD
Nonstop2h 56mAmerican Airlines
Deal found 4/14$256
This Southwest deal was found by Cheapflights users on 4/13. 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 6/271:50 pmORD - PWM
1 stop9h 15mSouthwest
Tue 7/15:30 amPWM - ORD
2 stops10h 30mSouthwest
Deal found 4/13$295

Cheapflights Fare Finder

Customize your flight search to find flights from O'Hare Intl 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 April 15, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Portland that are best for you.

Fly from

O'Hare Intl

Fly to

Portland

Route

Depart

Return

Price

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 6/3

9:00 am-5:43 pm

1 stop7h 43m

Portland

Wed 6/11

6:00 am-7:53 am

Nonstop2h 53m

$237

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 6/3

7:05 am-4:50 pm

2 stops8h 45m

Portland

Wed 6/11

6:03 am-4:59 pm

2 stops11h 56m

$239

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 5/9

4:15 pm-6:26 pm

1 stop25h 11m

Portland

Sun 5/11

8:23 pm-11:32 pm

1 stop28h 09m

$240

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 5/2

6:20 am-2:25 pm

1 stop7h 05m

Portland

Mon 5/5

3:20 pm-10:22 pm

1 stop8h 02m

$250

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 7/9

7:12 pm-10:46 pm

Nonstop2h 34m

Portland

Fri 7/11

6:00 am-7:56 am

Nonstop2h 56m

$256

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 6/27

1:50 pm-12:05 am

1 stop9h 15m

Portland

Tue 7/1

5:30 am-3:00 pm

2 stops10h 30m

$295

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 5/29

10:00 am-2:07 pm

2 stops27h 07m

Portland

Sun 6/1

3:15 pm-8:50 am

3 stops42h 35m

$443

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 7/4

4:50 pm-8:12 pm

Nonstop2h 22m

$90

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 5/31

3:13 pm-11:57 pm

1 stop7h 44m

$100

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 5/6

6:15 am-2:40 pm

1 stop7h 25m

$102

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/14

Showing 1-10 of 14 results
1
2

Compare providers for flights from O'Hare Intl 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 O'Hare Intl to Portland in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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 O'Hare Intl Airport-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 O'Hare Intl Airport-Portland, Maine flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Portland, Maine flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-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 O'Hare Intl Airport-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 O'Hare Intl to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from O'Hare Intl 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 O'Hare Intl Airport to Portland

How far ahead should I book a flight from Chicago O'Hare Intl Airport to Portland, Maine?

Use this chart to determine the optimal time to book a round-trip flight from O'Hare Intl to Portland. Price data was last updated on April 11, 2025.

To ensure you get the cheapest price possible for a flight from Chicago O'Hare Intl Airport to Portland, Maine, you should look to book at least 79 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Portland, Maine?

Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Portland, Maine (average of $296). Flying from Chicago O'Hare Intl Airport to Portland, Maine in May is currently the most expensive (average of $416). 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 ORD to PWM?

Find hourly flight availability from O'Hare Intl 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 April 15, 2025.

When flying from Chicago O'Hare Intl Airport to Portland, Maine, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 46% versus a flight in the morning.

What is the cheapest day to fly from Chicago O'Hare Intl Airport to Portland, Maine?

Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Portland. Price data was last updated on March 30, 2025.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to Portland, Maine

Explore weekly flight availability from O'Hare Intl 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 April 15, 2025.

The most flights from ORD to PWM are scheduled on a Monday (6 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (2 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 April 15, 2025.
Read through reviews of airlines operating flights from Chicago to Portland, such as Southwest, Delta and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,279 reviews

Food

7.1

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,279 reviews
Southwest
8.0
Very good
4,279 reviews

Food

7.1

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,916 reviews
Southwest
8.0
Very good
4,279 reviews

Food

7.1

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,656 reviews
Southwest
8.0
Very good
4,279 reviews

Food

7.1

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
JetBlue
7.3
Good
2,927 reviews
Southwest
8.0
Very good
4,279 reviews

Food

7.1

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,279 reviews

Food

7.1

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl 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 O'Hare Intl?

    For a flight from Chicago O'Hare Intl to Portland, you will be flying into Portland. Portland (PWM) is just 2.9 mi from the center of the city. Portland is the only Portland airport and it handles 4 inbound flights from Chicago O'Hare Intl per day. 4 airlines have flights to Portland from Chicago O'Hare Intl on a regular basis.

  • What are the cheapest airlines flying from Chicago O'Hare Intl Airport to Portland, Maine round-trip?

    According to our current data, United Airlines ($237), Delta ($239), and Frontier ($240) offers the cheapest pricing from Chicago O'Hare Intl Airport to Portland, Maine. You may be able to fly from Chicago O'Hare Intl Airport to Portland, Maine for 37% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to Portland, Maine one-way?

    The cheapest airlines for a one-way flight from Chicago O'Hare Intl Airport to Portland, Maine are American Airlines ($90), United Airlines ($100), and JetBlue ($102).

  • What are the most reliable airlines from Chicago O'Hare Intl Airport to Portland, Maine?

    The top 3 most reliable airlines when flying from Chicago O'Hare Intl Airport to Portland, Maine are SkyWest Airlines (85%), Air New Zealand (85%) and United Airlines (76%).

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Portland, Maine?

    While on average a flight from Chicago O'Hare Intl Airport to Portland, Maine is generally $284, our data shows the cheapest flight currently is $104. When looking at the most popular route, (Chicago O'Hare Intl - Portland), you can expect to pay $199 for that flight.

  • Can I find deals for flights from O'Hare Intl to Portland that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Portland?

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

  • Can I find deals for business class flights from O'Hare Intl to Portland?

    Yes. Cheapflights offers flight deals from O'Hare Intl 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 O'Hare Intl Airport to Portland, Maine?

    Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Portland, Maine (average of $296). Flying from Chicago O'Hare Intl Airport to Portland, Maine in May is currently the most expensive (average of $416). 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 O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport 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.

Top 4 airlines flying from O'Hare Intl to Portland

Discover the top 4 airlines that operate flights from O'Hare Intl 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 April 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$90FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$177Average$333FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$215Average$388FlexibilityNo cancel feeOn-time69%
DeltaCheapest$217Average$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.