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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 31/5. 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
25 Apr — 2 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 26 March 2026.

Fly to

Route

Depart

Return

Price

Cheapest return flight
Fastest return journey

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 6/5

06:00-07:56

Nonstop2h 56m

Chicago O'Hare Intl

Sat 9/5

17:56-21:19

Nonstop2h 23m

£197

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 23/5

16:58-18:58

Nonstop3h 00m

Chicago O'Hare Intl

Wed 27/5

18:18-21:51

Nonstop2h 33m

£197

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 5/5

06:00-07:56

Nonstop2h 56m

Chicago O'Hare Intl

Sat 9/5

17:56-21:19

Nonstop2h 23m

£201

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 15/7

06:00-08:00

Nonstop3h 00m

Chicago O'Hare Intl

Wed 22/7

18:08-21:41

Nonstop2h 33m

£201

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 22/5

16:51-18:51

Nonstop3h 00m

Chicago O'Hare Intl

Sun 24/5

10:55-14:26

Nonstop2h 31m

£201

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 11/6

16:51-18:51

Nonstop3h 00m

Chicago O'Hare Intl

Mon 15/6

10:55-14:26

Nonstop2h 31m

£201

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 10/4

06:04-08:00

Nonstop2h 56m

Chicago O'Hare Intl

Mon 20/4

18:10-21:40

Nonstop2h 30m

£216

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 9/4

06:04-08:00

Nonstop2h 56m

Chicago O'Hare Intl

Mon 20/4

18:10-21:40

Nonstop2h 30m

£216

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 15/4

18:33-20:43

Nonstop3h 10m

Chicago O'Hare Intl

Sun 19/4

18:10-21:40

Nonstop2h 30m

£230

PortlandChicago

PWM - ORD

PWMORD

Portland

Mon 13/7

06:00-08:00

Nonstop3h 00m

Chicago O'Hare Intl

Sat 18/7

18:08-21:41

Nonstop2h 33m

£246

Flights are sorted by cheapest return flights first.

Deals found on 21/3

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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