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Portland

$152+ 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 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
Jun 19 — Jun 261
Fri 6/19
Fri 6/26
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Portland are usually found in March or May, booked 64 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday

Cheap 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 May 20, 2026.

This American Airlines deal was found by Cheapflights users on 5/19. 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.
Tue 6/308:59 pm
ORD
-
PWM
Nonstop2h 43m
American Airlines
Tue 7/77:24 pm
PWM
-
ORD
Nonstop3h 06m
American Airlines
Deal found 5/19$297
This Delta deal was found by Cheapflights users on 5/17. 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.
Fri 7/36:00 pm
ORD
-
PWM
1 stop5h 52m
Delta
Sat 7/41:51 pm
PWM
-
ORD
1 stop7h 11m
Delta
Deal found 5/17$307
This United Airlines deal was found by Cheapflights users on 5/17. 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 6/106:18 pm
ORD
-
PWM
Nonstop2h 33m
United Airlines
Tue 6/165:00 pm
PWM
-
ORD
Nonstop3h 00m
United Airlines
Deal found 5/17$312
This United Airlines deal was found by Cheapflights users on 5/19. 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.
Sat 7/46:08 pm
ORD
-
PWM
Nonstop2h 33m
United Airlines
Sat 7/116:00 am
PWM
-
ORD
Nonstop3h 00m
United Airlines
Deal found 5/19$316
This Delta deal was found by Cheapflights users on 5/18. 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.
Tue 6/239:48 am
ORD
-
PWM
1 stop7h 04m
Delta
Tue 6/305:41 pm
PWM
-
ORD
1 stop6h 07m
Delta
Deal found 5/18$317
This United Airlines deal was found by Cheapflights users on 5/16. 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 5/286:18 pm
ORD
-
PWM
Nonstop2h 33m
United Airlines
Tue 6/26:00 am
PWM
-
ORD
Nonstop3h 00m
United Airlines
Deal found 5/16$324
This Delta deal was found by Cheapflights users on 5/16. 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 7/16:00 pm
ORD
-
PWM
1 stop5h 52m
Delta
Sat 7/46:25 am
PWM
-
ORD
1 stop11h 46m
Delta
Deal found 5/16$325
This United Airlines deal was found by Cheapflights users on 5/18. 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 7/86:08 pm
ORD
-
PWM
Nonstop2h 33m
United Airlines
Sat 7/116:00 am
PWM
-
ORD
Nonstop3h 00m
United Airlines
Deal found 5/18$326
This Delta deal was found by Cheapflights users on 5/16. 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 6/201:49 pm
ORD
-
PWM
1 stop8h 16m
Delta
Wed 6/2411:48 am
PWM
-
ORD
1 stop8h 43m
Delta
Deal found 5/16$327
This Delta deal was found by Cheapflights users on 5/15. 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 6/106:05 am
ORD
-
PWM
1 stop7h 14m
Delta
Tue 6/165:29 pm
PWM
-
ORD
1 stop6h 05m
Delta
Deal found 5/15$332
This United Airlines deal was found by Cheapflights users on 5/18. 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 6/236:18 pm
ORD
-
PWM
Nonstop2h 33m
United Airlines
Wed 8/127:40 am
PWM
-
ORD
Nonstop3h 03m
United Airlines
Deal found 5/18$333

Find 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 May 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$297
(American Airlines)

One-way from

$152
(Kiwi.com)

Popular in

December

Cheapest in

March

Average price

$322

Good round-trip deal

$304 or less

Good one-way deal

$174 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. 10% potential increase in price ($43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
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

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 May 20, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Portland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 9/2

8:45 am-2:38 pm

1 stop4h 53m

Portland

Sat 9/5

5:03 pm-7:00 pm

Nonstop2h 57m

$317

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 9/16

1:15 pm-11:59 pm

2 stops9h 44m

Portland

Wed 9/23

6:00 am-12:08 pm

1 stop7h 08m

$332

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 10/3

1:15 pm-11:59 pm

2 stops9h 44m

Portland

Wed 10/7

5:59 pm-10:35 pm

1 stop5h 36m

$332
Quickest round-trip

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 10/29

10:35 am-1:52 pm

Nonstop2h 17m

Portland

Mon 11/2

4:48 pm-6:45 pm

Nonstop2h 57m

$361

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 6/25

5:22 pm-12:25 am

1 stop6h 03m

Portland

Tue 6/30

1:25 pm-9:29 pm

1 stop9h 04m

$372

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 9/5

11:30 am-10:33 pm

2 stops10h 03m

Portland

Sun 9/6

6:00 am-4:48 pm

2 stops11h 48m

$384

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 6/13

6:18 pm-9:51 pm

Nonstop2h 33m

Portland

Sun 6/14

5:15 am-9:36 am

1 stop5h 21m

$392

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 9/17

6:00 am-1:21 pm

1 stop6h 21m

Portland

Mon 9/21

6:00 am-12:08 pm

1 stop7h 08m

$401

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 7/16

3:00 pm-11:51 pm

1 stop7h 51m

Portland

Fri 7/24

5:00 pm-7:00 pm

Nonstop3h 00m

$411

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 7/31

3:22 pm-11:14 pm

1 stop6h 52m

Portland

Sat 8/8

6:30 am-4:54 pm

2 stops11h 24m

$411

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/17

Showing 1-10 of 23 resultsSorted by cheapest first
1
2
3

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 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 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 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 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?

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 63 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, March is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Portland, Maine (average of $301). Flying from Chicago O'Hare Intl Airport to Portland, Maine in December is currently the most expensive (average of $471). 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 May 20, 2026.

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 19% 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 May 16, 2026.

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. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to Portland, Maine?

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 20, 2026.
Read through reviews of airlines operating flights from Chicago O'Hare Intl Airport to Portland, such as United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,736 reviews

Crew

8.1

Comfort

7.3

Food

6.6

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
United Airlines
7.4
Good
9,736 reviews
United Airlines
7.4
Good
9,736 reviews

Crew

8.1

Comfort

7.3

Food

6.6

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
American Airlines
7.1
Good
11,642 reviews
United Airlines
7.4
Good
9,736 reviews

Crew

8.1

Comfort

7.3

Food

6.6

Entertainment

7.1

Boarding

7.7

Overall

7.4

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.

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 3 inbound flights from Chicago O'Hare Intl per day. 2 airlines have flights to Portland from Chicago O'Hare Intl on a regular basis.

  • How long is the flight from Chicago O'Hare Intl Airport to Portland, Maine?

    Departing from Chicago O'Hare Intl Airport to Portland, Maine will take you 4h 53m. There are 897 mi between Chicago O'Hare Intl Airport and Portland, Maine. This flight may include one or multiple stops.

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

    According to our current data, United Airlines ($229), and American Airlines ($229) 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 38% less than the average price by searching for these airlines.

  • 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 Republic Airways (79%), American Airlines (78%) and Envoy Air (78%).

  • 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 $402, our data shows the cheapest flight currently is $134. When looking at the most popular route, (Chicago O'Hare Intl - Portland), you can expect to pay $297 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, March is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Portland, Maine (average of $301). Flying from Chicago O'Hare Intl Airport to Portland, Maine in December is currently the most expensive (average of $471). 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
Brunswick
Lewiston
Conway

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Alternative routes for O'Hare Intl to Portland

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Boston flights
Midway to Boston flights
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Top 2 airlines flying from O'Hare Intl to Portland

Discover the top 2 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 May 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$229Average$372FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$229Average$351FlexibilityNo cancel feeOn-time71%

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