
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $284 (Delta) |
One-way from | $96 (Priceline) |
Popular in | December |
Cheapest in | September |
Average price | $391 |
Good round-trip deal | $337 or less |
Good one-way deal | $189 or less |
Fly from
Fly to
Route
Depart
Return
Price
PortlandChicago
PWM - ORD
PWMORD
Portland
Thu 2/26
5:31 am-1:39 pm
1 stop9h 08m
Chicago O'Hare Intl
Mon 3/2
2:03 pm-11:22 pm
2 stops8h 19m
PortlandChicago
PWM - ORD
PWMORD
Portland
Mon 12/8
2:34 pm-12:01 am
2 stops10h 27m
Chicago O'Hare Intl
Sat 12/13
6:45 am-12:13 pm
1 stop4h 28m
PortlandChicago
PWM - MDW
PWMMDW
Portland
Thu 1/22
5:30 am-11:59 am
1 stop7h 29m
Chicago Midway
Sun 1/25
1:26 pm-11:22 pm
2 stops8h 56m
PortlandChicago
PWM - ORD
PWMORD
Portland
Mon 1/12
4:10 pm-6:18 pm
Nonstop3h 08m
Chicago O'Hare Intl
Wed 1/14
11:00 am-2:39 pm
Nonstop2h 39m
PortlandChicago
PWM - ORD
PWMORD
Portland
Thu 12/11
6:00 am-10:44 am
1 stop5h 44m
Chicago O'Hare Intl
Sat 12/13
5:50 pm-9:17 pm
Nonstop2h 27m
PortlandChicago
PWM - ORD
PWMORD
Portland
Thu 2/26
5:45 am-7:57 am
Nonstop3h 12m
Chicago O'Hare Intl
Mon 3/2
2:30 pm-8:28 pm
1 stop4h 58m
PortlandChicago
PWM - ORD
PWMORD
Portland
Tue 12/9
6:08 am-4:57 pm
2 stops11h 49m
Chicago O'Hare Intl
Sat 12/13
6:00 am-4:00 pm
2 stops9h 00m
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 12/5
2:34 pm-12:01 am
2 stops10h 27m
Chicago O'Hare Intl
Mon 12/8
1:01 pm-11:21 pm
2 stops9h 20m
PortlandChicago
PWM - MDW
PWMMDW
Portland
Thu 2/26
6:00 am-12:48 pm
2 stops7h 48m
Chicago Midway
Mon 3/2
12:46 pm-11:22 pm
2 stops9h 36m
PortlandChicago
PWM - MDW
PWMMDW
Portland
Sat 12/6
2:34 pm-11:47 pm
2 stops10h 13m
Chicago Midway
Sun 12/14
1:14 pm-11:21 pm
2 stops9h 07m
Currently, April is the cheapest month in which you can book a flight from Portland, Maine to Illinois (average of $89). Flying from Portland, Maine to Illinois in January is currently the most expensive (average of $123). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
It’s optimal to fly from Portland, Maine to Illinois in the evening. By choosing this option you can save up to 39% on the cost of your flight, compared to a flight in the morning.
Travelers seeking maximum savings on their Portland, Maine to Illinois flight should consider departing on Saturday evenings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from PWM to USIL are scheduled on a Thursday (5 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).
Comfort
Crew
Overall
Entertainment
Boarding
Food
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Crew
Overall
Entertainment
Boarding
Food
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Crew
Overall
Entertainment
Boarding
Food
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Crew
Overall
Entertainment
Boarding
Food
Reviews
Mike,Aug 2025
OKC - AUS
Comfort
Crew
Overall
Entertainment
Boarding
Food
Reviews
Mike,Aug 2025
OKC - AUS
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$124 | Average$352 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$203 | Average$304 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$229 | Average$423 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$246 | Average$390 | FlexibilityNo cancel fee | On-time63% |