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Portland

$59+ Cheap flights from Portland, ME

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 9/3. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ORD
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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What to know about flights from Portland

Discover essential information about flights departing from Portland, including flight schedules, destinations, airlines operating at the Portland airport, and any specific guidelines or requirements for travelers. Please note that the information is based on the most recent updates available. Data last updated August 18, 2025.

Cheapest one-way flight

$74

Cheapest round-trip flight

$94

Cheapest airline

American Airlines

Most popular destination

New York John F Kennedy Intl (JFK)

Good round-trip deal

$44 or less

Good one-way deal

$75 or less
The cheapest one-way flight from Portland is currently to Orlando.
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The cheapest round-trip flight from Portland is currently to Charleston.
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On average, American Airlines currently has the cheapest one-way flight from Portland (avg. price of $316).
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New York John F Kennedy Intl (JFK) is currently the most popular flight destination from Portland (average round-trip price of $219).
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Price to beat on a round-trip flight from Portland.
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Price to beat on a one-way flight from Portland.
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Find flights from Portland

Cheapest flights from Portland
Explore the most affordable flight options available from Portland. Find the lowest fares based on data from user searches, with prices last updated on August 18, 2025.

Sat 9/66:00 amPWM - EWR
Nonstop1h 32mUnited Airlines
Sat 9/134:59 pmEWR - PWM
Nonstop1h 27mUnited Airlines
Deal found 8/18$97
Thu 9/187:30 amPWM - EWR
Nonstop1h 29mUnited Airlines
Wed 9/247:59 amEWR - PWM
Nonstop1h 25mUnited Airlines
Deal found 8/18$109
Fri 9/194:55 pmPWM - LGA
Nonstop1h 29mDelta
Tue 9/309:22 amLGA - PWM
Nonstop1h 32mDelta
Deal found 8/18$117
Thu 9/42:36 pmPWM - JFK
Nonstop1h 32mDelta
Thu 9/410:50 pmJFK - PWM
Nonstop1h 58mDelta
Deal found 8/18$117
Sat 8/306:00 amPWM - EWR
Nonstop1h 32mUnited Airlines
Mon 9/14:59 pmEWR - PWM
Nonstop1h 27mUnited Airlines
Deal found 8/16$117
Thu 9/47:05 amPWM - LGA
Nonstop1h 26mAmerican Airlines
Mon 9/811:10 amLGA - PWM
Nonstop1h 21mAmerican Airlines
Deal found 8/17$118
Thu 9/46:00 amPWM - LGA
Nonstop1h 25mDelta
Sun 9/79:55 pmLGA - PWM
Nonstop1h 30mDelta
Deal found 8/18$127
Thu 9/46:33 pmPWM - JFK
1 stop5h 05mDelta
Fri 9/510:50 pmJFK - PWM
Nonstop1h 58mDelta
Deal found 8/18$127
Sun 11/25:00 amPWM - EWR
Nonstop1h 35mUnited Airlines
Wed 11/59:56 pmEWR - PWM
Nonstop1h 21mUnited Airlines
Deal found 8/16$127
Tue 9/167:05 amPWM - LGA
Nonstop1h 26mAmerican Airlines
Wed 9/1711:10 amLGA - PWM
Nonstop1h 21mAmerican Airlines
Deal found 8/17$137
Fri 10/106:50 amPWM - JFK
Nonstop1h 28mDelta
Mon 10/1310:30 pmJFK - PWM
Nonstop1h 35mDelta
Deal found 8/18$137
Thu 9/410:39 amPWM - EWR
Nonstop1h 33mUnited Airlines
Thu 9/49:32 pmEWR - PWM
Nonstop1h 31mUnited Airlines
Deal found 8/18$137

Find flights from Portland within your budget

 
Find flights departing from Portland that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on August 18, 2025. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

O'Hare Intl

Route

Depart

Return

Price

PortlandNewark

PWM - EWR

PWMEWR

Portland

Sat 9/6

6:00 am-7:32 am

Nonstop1h 32m

Newark

Sat 9/13

4:59 pm-6:26 pm

Nonstop1h 27m

$97

PortlandNewark

PWM - EWR

PWMEWR

Portland

Fri 9/26

5:41 pm-7:30 pm

Nonstop1h 49m

Newark

Sun 9/28

7:45 am-9:11 am

Nonstop1h 26m

$97

PortlandNewark

PWM - EWR

PWMEWR

Portland

Thu 9/18

7:30 am-8:59 am

Nonstop1h 29m

Newark

Wed 9/24

7:59 am-9:24 am

Nonstop1h 25m

$109

PortlandNew York

PWM - LGA

PWMLGA

Portland

Wed 9/3

7:00 am-8:23 am

Nonstop1h 23m

New York LaGuardia

Sat 9/6

10:02 am-11:26 am

Nonstop1h 24m

$117

PortlandNew York

PWM - LGA

PWMLGA

Portland

Fri 9/19

6:00 am-7:25 am

Nonstop1h 25m

New York LaGuardia

Sun 9/21

9:45 pm-11:03 pm

Nonstop1h 18m

$117

PortlandNew York

PWM - JFK

PWMJFK

Portland

Wed 9/3

7:30 am-8:49 am

Nonstop1h 19m

New York John F Kennedy Intl

Fri 9/5

8:30 pm-10:02 pm

Nonstop1h 32m

$117

PortlandNew York

PWM - LGA

PWMLGA

Portland

Fri 10/24

7:00 am-8:25 am

Nonstop1h 25m

New York LaGuardia

Sun 10/26

11:12 am-12:34 pm

Nonstop1h 22m

$117

PortlandNew York

PWM - LGA

PWMLGA

Portland

Fri 10/3

6:00 am-7:25 am

Nonstop1h 25m

New York LaGuardia

Sun 10/5

9:22 am-10:54 am

Nonstop1h 32m

$117

PortlandNew York

PWM - JFK

PWMJFK

Portland

Thu 9/4

2:17 pm-3:44 pm

Nonstop1h 27m

New York John F Kennedy Intl

Sat 9/6

12:00 pm-1:22 pm

Nonstop1h 22m

$117

PortlandNew York

PWM - LGA

PWMLGA

Portland

Fri 9/19

7:05 am-8:31 am

Nonstop1h 26m

New York LaGuardia

Sat 9/20

3:26 pm-4:50 pm

Nonstop1h 24m

$117

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 60 results
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Best time to book a flight from Portland

Have a flexible travel schedule? Discover the best time to fly from Portland 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 Portland

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

When is the best time to book a flight from Portland, Maine?

Use this chart to determine the optimal time to book a round-trip flight from Portland to O'Hare Intl. Price data was last updated on August 8, 2025.

To ensure you get the cheapest price possible for a flight from Portland, Maine, you should look to book at least 32 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 Portland, Maine?

Currently, September is the cheapest month in which you can book a flight from Portland, Maine (average of $59). Flying from Portland, Maine in July will prove the most costly (average of $135). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

When is the cheapest time to fly from Portland, Maine?

Use this chart to determine the cheapest time to fly round-trip from Portland to O'Hare Intl. Price data was last updated on August 17, 2025.

Those who are seeking the cheapest fare on flights departing from Portland, Maine would be wise to consider leaving during Saturday evenings when prices are typically at their lowest. When considering other options, price-conscious travelers should avoid Sunday afternoons when fares are usually the most expensive.

Which airlines fly from Portland, Maine?

For flights departing from Portland, Maine check dates and pricing for the following: United Airlines, American Airlines, Delta. These airlines depart to the following popular destinations: Chicago.

American Airlines
American Airlines
From $129
United Airlines
United Airlines
From $140
Delta
Delta
From $100
Southwest
Southwest
From $168

What are popular destinations to fly to from Portland, Maine?

Some of the most frequent flights departing from Portland, Maine everyday are: New York (482 flights per day), Detroit (106 flights per day), and Chicago (85 flights per day).

New York
New York
From $78
Washington, D.C.
Washington, D.C.
From $108
Chicago
Chicago
From $125
Philadelphia
Philadelphia
From $118

What is the cheapest place to fly to from Portland, Maine?

The cheapest city to fly to from Portland, Maine is Tweed-New Haven, with prices starting at $43. Explore other affordable destinations below.

Tweed-New Haven
Tweed-New Haven
From $43
Norfolk
Norfolk
From $66
Tampa
Tampa
From $71
Orlando
Orlando
From $74

Airline reviews for flights from Portland

Read reviews and ratings of airlines operating flights from Portland. Gain insights into the quality of service, in-flight amenities, customer experiences, and overall satisfaction to choose the best airline for your Portland travel. Please note that the reviews are sourced from user searches and were last updated on August 18, 2025. In the last 7 days, Cheapflights users made a total of 2,558,603 searches.
See what other customers who have flown with Delta, United Airlines, and American Airlines from Portland have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,925 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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Related info for your journey

Access useful and relevant information related to your journey from Portland. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated August 18, 2025.

  • What are the most popular destinations to fly to from Portland, Maine?

    This month, the top selected destinations from Portland, Maine are Denver, Orlando Airport, Chicago. Throughout the year, Orlando Airport, Denver, Washington, D.C. Reagan-National Airport are some of the top choices made by users flying from Portland, Maine.

  • What is the cheapest flight from Portland, Maine to anywhere?

    Users have flown out of Portland, Maine for as low as $43 to New Haven (prices may vary depending on the airline and departure time). On average, users have booked flights for $409 to fly from Portland, Maine.

  • What are the cheapest airlines flying from Portland, Maine to anywhere?

    Over the past few days, we've found that Frontier, Breeze Airways, and JetBlue have the cheapest prices from Portland, Maine. Frontier flights from Portland, Maine to Atlanta Hartsfield-Jackson ($58), Breeze Airways flights from Portland, Maine to Charleston ($67), and JetBlue flights from Portland, Maine to Amsterdam Schiphol ($81).

  • What is the cheapest premium economy flight from Portland, Maine?

    Options for some of the cheapest premium economy flights from Portland, Maine we have found on Cheapflights are as follows:
    Fly from Portland to Orlando Airport starting at $198
    Fly from Portland to Fort Myers starting at $214
    Fly from Portland to Raleigh starting at $278
    Fly from Portland to Tampa starting at $328

  • What is the cheapest first class flight from Portland, Maine?

    If you’re looking for a cheap first-class flight from Portland, Maine, consider New York. Prices start at $462 so you can fly first-class even on a budget.

  • What is the cheapest month to fly from Portland, Maine?

    September is currently the cheapest month to fly from Portland, Maine. At this moment in time July is the most expensive month. These prices are determined by multiple factors and booking in advance can help keep costs down if your schedule is not as flexible.

  • Where are the cheapest places to fly to from Portland, Maine?

    Check out the cheapest flights from Portland, Maine to embark to:
    Fly from Portland to New York from $97 round trip
    Fly from Portland to Charleston from $127 round trip
    Fly from Portland to Orlando from $142 round trip
    Fly from Portland to Detroit from $161 round trip
    Fly from Portland to Raleigh from $162 round trip

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