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$100+ 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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
Aug 6 — Aug 131
Wed 8/6
Wed 8/13
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Portland are usually found in September or August, booked 86 days in advance, depart on a Tuesday or Sunday 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 August 1, 2025.

Round-trip from

$233
(JetBlue)

One-way from

$100
(American Airlines)

Popular in

November

Cheapest in

September

Average price

$319

Good round-trip deal

$299 or less

Good one-way deal

$151 or less
From Chicago O'Hare Intl to Portland
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One-way flight from Chicago O'Hare Intl to Portland
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Highest demand for flights based on searches. 13% potential increase in price ($60 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Chicago O'Hare Intl to Portland.
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Price to beat on a one-way flight from Chicago O'Hare Intl to Portland.
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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 August 1, 2025.

This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/276:15 amORD - PWM
1 stop6h 08mJetBlue
Wed 9/37:30 amPWM - ORD
1 stop5h 40mJetBlue
Deal found 7/30$233
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 9/310:05 amORD - PWM
Nonstop2h 37mAmerican Airlines
Tue 9/91:02 pmPWM - ORD
1 stop5h 49mAmerican Airlines
Deal found 7/31$234
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 8/232:25 pmORD - PWM
2 stops8h 38mDelta
Sat 8/305:30 pmPWM - ORD
1 stop7h 26mDelta
Deal found 7/31$240
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 10/26:10 pmORD - PWM
Nonstop2h 34mUnited Airlines
Tue 10/76:14 amPWM - ORD
Nonstop2h 51mUnited Airlines
Deal found 7/30$257
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/82:55 pmORD - PWM
2 stops7h 25mSouthwest
Wed 9/105:50 amPWM - ORD
2 stops13h 05mSouthwest
Deal found 7/30$268

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 August 1, 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

Wed 8/27

6:15 am-1:23 pm

1 stop6h 08m

Portland

Wed 9/3

7:30 am-12:10 pm

1 stop5h 40m

$233

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 9/3

10:05 am-1:42 pm

Nonstop2h 37m

Portland

Tue 9/9

1:02 pm-5:51 pm

1 stop5h 49m

$234

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 8/23

2:25 pm-12:03 am

2 stops8h 38m

Portland

Sat 8/30

5:30 pm-11:56 pm

1 stop7h 26m

$240

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 10/2

6:10 pm-9:44 pm

Nonstop2h 34m

Portland

Tue 10/7

6:14 am-8:05 am

Nonstop2h 51m

$257

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Mon 9/8

2:55 pm-11:20 pm

2 stops7h 25m

Portland

Wed 9/10

5:50 am-5:55 pm

2 stops13h 05m

$268

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 8/30

8:13 pm-11:59 pm

Nonstop2h 46m

$100

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Mon 9/22

6:45 am-1:22 pm

1 stop5h 37m

$102

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 9/2

6:25 pm-9:59 pm

Nonstop2h 34m

$109

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 8/31

5:45 am-12:29 pm

1 stop5h 44m

$110

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 8/24

8:00 am-11:34 am

1 stop26h 34m

$125

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 13 results
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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 July 25, 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 86 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 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 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 August 1, 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 evening, which can drop the price by up to 20% 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 July 27, 2025.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Portland, Maine flight should consider departing on Tuesday evenings 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 August 1, 2025.

The most flights from ORD to PWM are scheduled on a Thursday (10 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (5 on average).

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, 2025.
Read through reviews of airlines operating flights from Chicago O'Hare Intl Airport 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
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
JetBlue
7.3
Good
2,914 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 7 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, JetBlue ($233), American Airlines ($234), and Delta ($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 40% 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 ($100), JetBlue ($102), and United Airlines ($109).

  • 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 Envoy Air (90%), American Airlines (77%) and Air New Zealand (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 $286, our data shows the cheapest flight currently is $100. When looking at the most popular route, (Chicago O'Hare Intl - Portland), you can expect to pay $193 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 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.

See more FAQs

Traveling to a place near Portland?

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

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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 August 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$68Average$160FlexibilityNo cancel feeOn-time62%
DeltaCheapest$163Average$479FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$203Average$343FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$213Average$388FlexibilityNo cancel feeOn-time69%

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