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$55+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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The best prices from Chicago O'Hare Intl to Portland are usually found in July or June, booked 83 days in advance, depart on a Tuesday or Saturday 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 January 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$160
(Booking.com)

One-way from

$55
(Frontier)

Popular in

April

Cheapest in

July

Average price

$412
Provider with most accurate pricing for Chicago O'Hare Intl-Portland flight deals.
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Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Portland flights.
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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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High demand for flights, 12% potential price rise
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Best time to find cheap flights, 3% potential price drop
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Average for round-trip flights in January 2025
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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 January 21, 2025.

This Booking.com deal was found by Cheapflights users on 1/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/110:20 amORD - PWM
1 stop21h 58mFrontier
Mon 3/38:35 pmPWM - ORD
1 stop17h 45mFrontier
Deal found 1/20$160
This JetBlue Airways deal was found by Cheapflights users on 1/20. 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 Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/316:20 amORD - PWM
1 stop6h 00mJetBlue
Sat 6/72:15 pmPWM - ORD
1 stop9h 05mJetBlue
Deal found 1/20$185
This American Airlines deal was found by Cheapflights users on 1/21. 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 7/56:20 pmORD - PWM
Nonstop2h 30mAmerican Airlines
Wed 7/97:19 amPWM - ORD
Nonstop2h 51mAmerican Airlines
Deal found 1/21$209
This Southwest deal was found by Cheapflights users on 1/20. 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.
Wed 3/57:00 amORD - PWM
1 stop4h 30mSouthwest
Tue 3/116:00 amPWM - ORD
1 stop8h 05mSouthwest
Deal found 1/20$217
This Delta deal was found by Cheapflights users on 1/20. 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.
Thu 4/36:00 amORD - PWM
1 stop4h 28mDelta
Sun 4/67:00 amPWM - ORD
1 stop6h 41mDelta
Deal found 1/20$223
This United Airlines deal was found by Cheapflights users on 1/20. 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.
Fri 10/316:00 pmORD - PWM
Nonstop2h 27mUnited Airlines
Sun 11/25:00 amPWM - ORD
1 stop5h 47mUnited Airlines
Deal found 1/20$252
This Mytrip deal was found by Cheapflights users on 1/20. 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.
Sat 3/15:15 amORD - PWM
2 stops13h 12mMultiple Airlines
Mon 3/36:18 pmPWM - ORD
2 stops28h 45mMultiple Airlines
Deal found 1/20$297
This Sun Country Air deal was found by Cheapflights users on 1/20. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/278:10 pmORD - PWM
1 stop14h 25mSun Country Air
Fri 8/812:32 pmPWM - ORD
1 stop7h 39mSun Country Air
Deal found 1/20$330

Find flights from O'Hare Intl to Portland within your budget

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 3/1

10:20 am-9:18 am

1 stop21h 58m

Portland

Mon 3/3

8:35 pm-1:20 pm

1 stop17h 45m

$160

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 2/9

11:10 am-2:42 pm

Nonstop2h 32m

Portland

Sun 2/16

4:53 pm-6:55 pm

Nonstop3h 02m

$209

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 2/16

10:30 am-4:03 pm

1 stop4h 33m

Portland

Sat 2/22

4:46 pm-9:15 pm

1 stop5h 29m

$229

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 2/8

6:00 am-1:54 pm

1 stop6h 54m

Portland

Sat 2/22

5:35 am-10:35 am

1 stop6h 00m

$239

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 3/1

5:15 am-7:27 pm

2 stops13h 12m

Portland

Mon 3/3

6:18 pm-10:03 pm

2 stops28h 45m

$297

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 2/15

1:30 pm-11:15 pm

2 stops8h 45m

Portland

Tue 2/25

5:35 am-4:45 pm

2 stops12h 10m

$344

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 2/26

7:25 am-5:38 pm

1 stop9h 13m

$55

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Mon 4/7

1:22 pm-11:00 pm

1 stop8h 38m

$87

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 3/18

6:36 pm-12:15 am

1 stop4h 39m

$115

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 3/13

3:00 pm-11:15 pm

1 stop7h 15m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 13 results
1
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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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy2 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*1 star
CheapTicketsDealPrice 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 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.

Travel insights for flights from O'Hare Intl to Portland

Get recent, data-driven insights about flights from O'Hare Intl to Portland including ideal travel times, pricing trends, and more.

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 January 17, 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 April is currently the most expensive (average of $498). 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 January 21, 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 40% 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 December 16, 2024.

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 January 21, 2025.

The most flights from ORD to PWM are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, 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 January 21, 2025.
Read through reviews of airlines operating flights from Chicago to Portland, such as Delta, Frontier and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,201 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,982 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,659 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 2 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, Frontier ($160), JetBlue ($185), and United Airlines ($209) 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 60% 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 Frontier ($55), JetBlue ($82), and Southwest ($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 Republic Airways (86%), United Airlines (85%) and Air New Zealand (85%).

  • 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 $301, 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 $177 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 April is currently the most expensive (average of $498). 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
Bath
North Conway
Brunswick
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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$38Average$92FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$182Average$340FlexibilityNo cancel feeOn-time71%
DeltaCheapest$217Average$318FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$221Average$406FlexibilityNo cancel feeOn-time69%
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