
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $279 (Delta) |
One-way from | $105 (United Airlines) |
Popular in | November |
Cheapest in | February |
Average price | $473 |
Good round-trip deal | $391 or less |
Good one-way deal | $231 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Thu 11/27
7:00 am-1:50 pm
1 stop5h 50m
Portland
Mon 12/1
4:53 pm-8:29 pm
1 stop4h 36m
ChicagoPortland
MDW - PWM
MDWPWM
Chicago Midway
Wed 12/31
3:29 pm-10:43 pm
1 stop6h 14m
Portland
Wed 1/7
5:30 am-10:34 am
1 stop6h 04m
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Thu 11/20
7:00 am-1:50 pm
1 stop5h 50m
Portland
Wed 12/3
6:15 am-4:42 pm
2 stops11h 27m
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Sat 11/22
5:23 am-12:30 pm
1 stop6h 07m
Portland
Thu 12/4
2:34 pm-12:01 am
2 stops10h 27m
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Sat 11/22
6:45 am-12:08 pm
1 stop4h 23m
Portland
Wed 12/3
6:15 am-4:42 pm
2 stops11h 27m
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Thu 11/20
5:23 am-12:30 pm
1 stop6h 07m
Portland
Thu 12/4
2:34 pm-12:01 am
2 stops10h 27m
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Sun 11/23
6:45 am-4:00 pm
2 stops8h 15m
Portland
Wed 12/3
4:43 pm-8:38 pm
1 stop4h 55m
ChicagoPortland
MDW - PWM
MDWPWM
Chicago Midway
Thu 1/1
3:29 pm-10:43 pm
1 stop6h 14m
Portland
Tue 1/6
6:00 am-4:31 pm
2 stops11h 31m
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Wed 11/19
10:53 am-2:12 pm
Nonstop2h 19m
Portland
Tue 12/2
3:00 pm-8:07 pm
1 stop6h 07m
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Fri 11/21
10:53 am-2:12 pm
Nonstop2h 19m
Portland
Fri 11/28
5:30 am-9:46 am
1 stop5h 16m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars |
The best time to book flights from Chicago to Portland, Maine is 58 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Currently, January is the cheapest month in which you can book a flight from Chicago to Portland, Maine (average of $88). Flying from Chicago to Portland, Maine in February is currently the most expensive (average of $137). 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.
One of the essential ways to save on airfare from Chicago to Portland, Maine is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 25% on airfare.
Travelers seeking maximum savings on their Chicago to Portland, Maine flight should consider departing on Sunday afternoons when fares are most often at their lowest. Thursday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from CHI to PWM are scheduled on a Monday (6 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 on average).
Crew
Comfort
Entertainment
Food
Overall
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Comfort
Entertainment
Food
Overall
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Comfort
Entertainment
Food
Overall
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Comfort
Entertainment
Food
Overall
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Comfort
Entertainment
Food
Overall
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Comfort
Entertainment
Food
Overall
Boarding
Reviews
Mike,Aug 2025
OKC - AUS
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$163 | Average$479 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$226 | Average$381 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$232 | Average$352 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$313 | Average$411 | FlexibilityNo cancel fee | On-time63% |