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£94+ 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 8/5. 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
15 Apr — 22 Apr1
1 adult
1 adult, Economy, 0 bags

Direct flights from Portland

Enter your travel dates to find the best prices.

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 16 March 2026.

Thu 21/516:51
PWM
-
ORD
Nonstop3h 00m
United Airlines
Mon 25/518:18
ORD
-
PWM
Nonstop2h 33m
United Airlines
Deal found 12/3£188
Wed 15/706:00
PWM
-
ORD
Nonstop3h 00m
United Airlines
Sat 18/718:18
ORD
-
PWM
Nonstop2h 33m
United Airlines
Deal found 11/3£203
Sat 11/418:33
PWM
-
ORD
Nonstop3h 10m
United Airlines
Sat 18/413:55
ORD
-
PWM
Nonstop2h 37m
United Airlines
Deal found 12/3£217
Fri 27/305:45
PWM
-
ORD
Nonstop3h 12m
United Airlines
Mon 30/318:10
ORD
-
PWM
Nonstop2h 30m
United Airlines
Deal found 11/3£218
Tue 14/416:28
PWM
-
ORD
Nonstop3h 10m
United Airlines
Fri 17/418:10
ORD
-
PWM
Nonstop2h 30m
United Airlines
Deal found 11/3£219
Mon 13/406:04
PWM
-
ORD
Nonstop2h 56m
United Airlines
Tue 14/410:45
ORD
-
PWM
Nonstop2h 35m
United Airlines
Deal found 12/3£231
Tue 7/706:00
PWM
-
ORD
Nonstop3h 00m
United Airlines
Sun 12/718:18
ORD
-
PWM
Nonstop2h 33m
United Airlines
Deal found 12/3£241
Fri 12/618:19
PWM
-
ORD
Nonstop3h 09m
United Airlines
Sun 14/610:55
ORD
-
PWM
Nonstop2h 31m
United Airlines
Deal found 11/3£244
Sat 11/418:33
PWM
-
ORD
Nonstop3h 10m
United Airlines
Sun 12/418:10
ORD
-
PWM
Nonstop2h 30m
United Airlines
Deal found 12/3£245
Thu 9/406:04
PWM
-
ORD
Nonstop2h 56m
United Airlines
Thu 16/418:10
ORD
-
PWM
Nonstop2h 30m
United Airlines
Deal found 12/3£250
Wed 8/718:25
PWM
-
ORD
Nonstop3h 09m
United Airlines
Sun 12/718:18
ORD
-
PWM
Nonstop2h 33m
United Airlines
Deal found 12/3£255
Sat 4/418:33
PWM
-
ORD
Nonstop3h 10m
United Airlines
Tue 7/413:55
ORD
-
PWM
Nonstop2h 37m
United Airlines
Deal found 13/3£256

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 16 March 2026.

Fly to

Route

Depart

Return

Price

Cheapest return flight
Fastest return journey

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 30/4

09:00-10:56

Nonstop2h 56m

Chicago O'Hare Intl

Mon 4/5

06:55-10:23

Nonstop2h 28m

£188

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 5/5

16:50-18:48

Nonstop2h 58m

Chicago O'Hare Intl

Sat 9/5

06:55-10:23

Nonstop2h 28m

£188

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 21/5

06:00-08:00

Nonstop3h 00m

Chicago O'Hare Intl

Tue 26/5

18:18-21:52

Nonstop2h 34m

£188

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 2/4

18:33-20:43

Nonstop3h 10m

Chicago O'Hare Intl

Tue 7/4

13:55-17:32

Nonstop2h 37m

£188

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 18/6

06:00-08:00

Nonstop3h 00m

Chicago O'Hare Intl

Sun 21/6

18:18-21:51

Nonstop2h 33m

£188

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 4/6

06:00-08:00

Nonstop3h 00m

Chicago O'Hare Intl

Mon 8/6

18:18-21:51

Nonstop2h 33m

£188

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 11/4

18:33-20:43

Nonstop3h 10m

Chicago O'Hare Intl

Sat 18/4

13:55-17:32

Nonstop2h 37m

£217

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 5/6

18:19-20:28

Nonstop3h 09m

Chicago O'Hare Intl

Sun 7/6

18:18-21:51

Nonstop2h 33m

£218

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 26/3

05:45-07:57

Nonstop3h 12m

Chicago O'Hare Intl

Mon 30/3

18:10-21:40

Nonstop2h 30m

£218

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 9/4

06:04-08:00

Nonstop2h 56m

Chicago O'Hare Intl

Sun 12/4

18:10-21:40

Nonstop2h 30m

£218

Flights are sorted by cheapest return flights first.

Deals found on 12/3

Showing 1-10 of 42 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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