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£88+ Cheap flights from Portland, Maine

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 16/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
PWM — BUD
18 May — 25 May1
1 adult
1 adult, Economy, 0 bags

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 18 April 2026. In the last 7 days, Cheapflights users made a total of 858,174 searches

Fly to

Route

Depart

Return

Price

Cheapest return flight

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 29/5

06:00-08:00

Nonstop3h 00m

Chicago O'Hare Intl

Sat 30/5

18:18-21:51

Nonstop2h 33m

£199

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 4/6

18:25-20:34

Nonstop3h 09m

Chicago O'Hare Intl

Sat 6/6

18:12-23:51

1 stop4h 39m

£206

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 22/5

06:00-08:00

Nonstop3h 00m

Chicago O'Hare Intl

Sun 24/5

15:53-23:51

1 stop6h 58m

£206

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 29/5

12:50-21:53

2 stops10h 03m

Chicago O'Hare Intl

Sat 30/5

09:25-16:07

1 stop5h 42m

£217

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 16/5

14:38-21:56

1 stop8h 18m

Chicago O'Hare Intl

Tue 19/5

14:00-00:43

2 stops9h 43m

£217

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 28/5

12:50-23:59

2 stops12h 09m

Chicago O'Hare Intl

Sat 30/5

06:24-16:07

2 stops8h 43m

£222

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 19/5

06:02-16:56

2 stops11h 54m

Chicago O'Hare Intl

Sun 24/5

07:00-11:55

1 stop3h 55m

£234

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 11/6

11:02-18:29

2 stops8h 27m

Chicago O'Hare Intl

Mon 15/6

06:40-16:49

2 stops9h 09m

£236

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 26/5

06:02-13:47

2 stops8h 45m

Chicago O'Hare Intl

Fri 29/5

14:00-00:43

2 stops9h 43m

£236
Fastest return journey

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 30/4

16:50-18:48

Nonstop2h 58m

Chicago O'Hare Intl

Sun 3/5

17:56-21:19

Nonstop2h 23m

£242

Flights are sorted by cheapest return flights first.

Deals found on 16/4

Showing 1-10 of 60 resultsSorted by cheapest first
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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 return 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.

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

If you’re flying from Portland, Maine, these routes are more frequently taken by airlines New York (424 flights per day), Chicago (110 flights per day) and Detroit (104 flights per day).

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From £288
New York
New York
From £210

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

The cheapest city to fly to from Portland, Maine is New York, with prices starting at £210. Explore other affordable destinations below.

New York
New York
From £210
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From £288

Browse thousands of different options on Cheapflights for your next trip

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Direct flights from Maine

Book a direct flight from one of these other cities located in Maine.
Direct flights from Bangor

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 18 April 2026.

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

    This month, the top selected destinations from Portland, Maine are Orlando Airport, Orlando, New York. Throughout the year, Orlando Airport, New York, Denver 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 £210 to New York John F Kennedy Intl Airport (prices may vary depending on the airline and departure time). On average, users have booked flights for £249 to fly from Portland, Maine.

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

    Here are some of the cheapest offers we have found for the cheapest premium economy flights from Portland, Maine.
    Portland to Washington, D.C. Dulles Intl Airport from £558

  • How does Cheapflights help users find flights from Portland?

    Cheapflights makes it easy to find flights from Portland by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

  • Why should you use Cheapflights to find cheap flight tickets from Portland?

    Cheapflights helps you find that perfect flight from Portland by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

  • Can Cheapflights find flights from Portland with no change fees?

    Users can book flights with no change fees policies with our dedicated filters. Book flights from Portland flexibly with Cheapflights today.

  • Can Cheapflights notify me if prices for flights from Portland become cheaper?

    Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and use a valid email address to enable the Price Alerts feature. That’s it!

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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Portland?

Cheapflights makes it easy to find flights from Portland by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Portland?

Cheapflights helps you find that perfect flight from Portland by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Portland with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Portland flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights from Portland become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and use a valid email address to enable the Price Alerts feature. That’s it!

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