£97+ 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 13/12. 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.
Direct flights from Portland
Cheapest flights from PortlandExplore the most affordable flight options available from Portland. Find the lowest fares based on data from user searches, with prices last updated on 15 September 2025.
Explore the most affordable flight options available from Portland. Find the lowest fares based on data from user searches, with prices last updated on 15 September 2025.
Find direct flights from Portland within your budget
Fly to
Route
Depart
Return
Price
PortlandChicago
PWM - ORD
PWMORD
Portland
Sat 1/11
16:51-18:52
Nonstop3h 01m
Chicago O'Hare Intl
Tue 4/11
18:15-21:50
Nonstop2h 35m
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 17/10
06:14-08:05
Nonstop2h 51m
Chicago O'Hare Intl
Sun 19/10
11:05-14:33
Nonstop2h 28m
PortlandChicago
PWM - ORD
PWMORD
Portland
Thu 9/10
06:14-08:05
Nonstop2h 51m
Chicago O'Hare Intl
Sun 12/10
13:55-17:42
Nonstop2h 47m
PortlandChicago
PWM - ORD
PWMORD
Portland
Thu 2/10
06:14-08:05
Nonstop2h 51m
Chicago O'Hare Intl
Sat 4/10
18:10-21:44
Nonstop2h 34m
PortlandChicago
PWM - ORD
PWMORD
Portland
Thu 2/10
16:57-18:48
Nonstop2h 51m
Chicago O'Hare Intl
Mon 6/10
18:10-21:44
Nonstop2h 34m
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 17/10
18:25-20:25
Nonstop3h 00m
Chicago O'Hare Intl
Mon 20/10
18:10-21:44
Nonstop2h 34m
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 7/11
16:54-18:55
Nonstop3h 01m
Chicago O'Hare Intl
Sun 9/11
10:53-14:12
Nonstop2h 19m
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 14/11
16:54-18:55
Nonstop3h 01m
Chicago O'Hare Intl
Mon 17/11
10:53-14:12
Nonstop2h 19m
PortlandChicago
PWM - ORD
PWMORD
Portland
Sun 23/11
16:53-18:55
Nonstop3h 02m
Chicago O'Hare Intl
Fri 28/11
10:53-14:12
Nonstop2h 19m
PortlandDenver
PWM - DEN
PWMDEN
Portland
Fri 31/10
15:20-18:21
Nonstop5h 01m
Denver Intl
Wed 5/11
10:05-15:48
Nonstop3h 43m