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£101+ Direct 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 11/5. 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 — LHR
9 May — 16 May1
1 adult
1 adult, Economy, 0 bags

Find direct flights from Portland within your budget

 
Use the slider to find direct flights from Portland within your budget. Price data is based on user searches made on Cheapflights. Over the past seven days, Cheapflights users made 858,174 searches. This data was last updated on 9 April 2026.

Fly to

Route

Depart

Return

Price

Cheapest return flight

PortlandChicago

PWM - ORD

PWMORD

Portland

Sun 24/5

06:00-08:00

Nonstop3h 00m

Chicago O'Hare Intl

Wed 27/5

10:55-14:26

Nonstop2h 31m

£200

PortlandChicago

PWM - ORD

PWMORD

Portland

Sun 31/5

06:00-08:00

Nonstop3h 00m

Chicago O'Hare Intl

Mon 1/6

18:18-21:51

Nonstop2h 33m

£200

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 30/4

16:50-18:48

Nonstop2h 58m

Chicago O'Hare Intl

Sat 2/5

10:48-14:14

Nonstop2h 26m

£200

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 27/5

16:51-18:51

Nonstop3h 00m

Chicago O'Hare Intl

Sun 31/5

18:18-21:51

Nonstop2h 33m

£215

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 1/5

16:50-18:49

Nonstop2h 59m

Chicago O'Hare Intl

Mon 4/5

06:55-10:23

Nonstop2h 28m

£215

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 15/5

06:00-07:56

Nonstop2h 56m

Chicago O'Hare Intl

Sun 17/5

06:55-10:23

Nonstop2h 28m

£215

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 12/6

16:51-18:51

Nonstop3h 00m

Chicago O'Hare Intl

Sun 14/6

18:18-21:51

Nonstop2h 33m

£215
Fastest return journey

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 15/5

06:00-07:56

Nonstop2h 56m

Chicago O'Hare Intl

Mon 18/5

17:56-21:20

Nonstop2h 24m

£224

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 2/5

16:50-18:48

Nonstop2h 58m

Chicago O'Hare Intl

Tue 5/5

10:48-14:14

Nonstop2h 26m

£260

PortlandChicago

PWM - ORD

PWMORD

Portland

Sun 24/5

18:25-20:34

Nonstop3h 09m

Chicago O'Hare Intl

Thu 28/5

10:55-14:26

Nonstop2h 31m

£260

Flights are sorted by cheapest return flights first.

Deals found on 6/4

Showing 1-10 of 38 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.

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