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£110+ 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 26/5. 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
6 Jun — 13 Jun1
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 7 May 2026.

Fly to

Route

Depart

Return

Price

Cheapest return flight

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 2/6

17:00-19:00

Nonstop3h 00m

Chicago O'Hare Intl

Tue 9/6

11:00-14:29

Nonstop2h 29m

£229

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 17/6

06:00-08:00

Nonstop3h 00m

Chicago O'Hare Intl

Wed 17/6

18:18-21:51

Nonstop2h 33m

£233

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 6/6

17:00-19:00

Nonstop3h 00m

Chicago O'Hare Intl

Mon 8/6

18:18-21:51

Nonstop2h 33m

£235

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 20/5

16:50-18:48

Nonstop2h 58m

Chicago O'Hare Intl

Tue 26/5

10:55-14:26

Nonstop2h 31m

£251

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 6/8

06:00-08:00

Nonstop3h 00m

Chicago O'Hare Intl

Tue 11/8

18:25-22:01

Nonstop2h 36m

£255

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 11/6

17:00-19:00

Nonstop3h 00m

Chicago O'Hare Intl

Sat 13/6

18:18-21:51

Nonstop2h 33m

£259

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 6/6

06:00-08:00

Nonstop3h 00m

Chicago O'Hare Intl

Sun 7/6

18:18-21:51

Nonstop2h 33m

£260

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 1/7

06:00-08:00

Nonstop3h 00m

Chicago O'Hare Intl

Thu 9/7

18:08-21:41

Nonstop2h 33m

£264
Fastest return journey

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 23/10

16:48-18:45

Nonstop2h 57m

Chicago O'Hare Intl

Mon 26/10

18:00-21:27

Nonstop2h 27m

£268

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 1/9

06:00-07:55

Nonstop2h 55m

Chicago O'Hare Intl

Wed 2/9

06:35-10:12

Nonstop2h 37m

£277

Flights are sorted by cheapest return flights first.

Deals found on 2/5

Showing 1-10 of 37 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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