Most accurate provider | FlightHub 3 stars |
---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $229 (American Airlines) |
One-way from | $90 (United Airlines) |
Popular in | December |
Cheapest in | February |
Average price | $425 |
Good round-trip deal | $297 or less |
Good one-way deal | $129 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Sat 4/19
6:12 pm-9:35 pm
Nonstop2h 23m
Portland
Thu 4/24
6:45 pm-11:29 pm
1 stop5h 44m
ChicagoPortland
MDW - PWM
MDWPWM
Chicago Midway
Mon 6/30
5:05 am-10:40 am
1 stop4h 35m
Portland
Thu 7/3
1:20 pm-5:25 pm
1 stop5h 05m
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Sat 5/31
6:10 am-1:20 pm
1 stop6h 10m
Portland
Sat 6/7
2:15 pm-10:20 pm
1 stop9h 05m
ChicagoPortland
MDW - PWM
MDWPWM
Chicago Midway
Tue 7/1
4:24 pm-12:28 am
1 stop7h 04m
Portland
Thu 7/3
11:44 am-5:45 pm
1 stop7h 01m
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Tue 5/27
8:00 am-11:32 am
Nonstop2h 32m
Portland
Fri 5/30
12:08 pm-1:58 pm
Nonstop2h 50m
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Sat 5/31
4:25 pm-11:59 pm
1 stop6h 34m
Portland
Sat 6/7
6:35 am-1:04 pm
1 stop7h 29m
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Fri 4/11
9:54 am-9:12 am
1 stop22h 18m
Portland
Sun 4/13
10:08 am-8:44 am
1 stop23h 36m
ChicagoPortland
MDW - PWM
MDWPWM
Chicago Midway
Fri 5/9
1:19 pm-6:26 pm
1 stop28h 07m
Portland
Sun 5/11
8:23 pm-12:24 pm
1 stop17h 01m
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Thu 5/8
6:00 am-3:55 pm
2 stops8h 55m
Portland
Sun 5/11
5:40 am-11:50 am
1 stop7h 10m
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Thu 5/22
4:35 pm-7:37 pm
2 stops26h 02m
Portland
Thu 5/29
12:47 pm-7:09 pm
1 stop7h 22m
Provider | Price Accuracy | Trust Score* |
---|---|---|
Price Accuracy1 star | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*3 stars | |
Price Accuracy3 stars | Trust Score*3 stars |
The best time to book flights from Chicago to Portland, Maine is 61 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 $296). Flying from Chicago to Portland, Maine in May is currently the most expensive (average of $416). 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 45% on airfare.
Travelers seeking maximum savings on their Chicago to Portland, Maine flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Friday mornings 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 Thursday, which is when the least amount of flights are scheduled (2 on average).
In terms of precipitation, rainfall in Portland, Maine ranges from 2.9 - 4.5 inches per month. November is typically the wettest month, when rainfall can reach 4.5 in. August is typically the driest time to visit Portland, Maine when rainfall is around 2.9 in.
If weather is an important factor for your trip to Portland, Maine, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
Food
Crew
Entertainment
Overall
Boarding
Comfort
Reviews
Ila,Mar 2025
HOU - DAL
Food
Crew
Entertainment
Overall
Boarding
Comfort
Reviews
Ila,Mar 2025
HOU - DAL
Food
Crew
Entertainment
Overall
Boarding
Comfort
Reviews
Ila,Mar 2025
HOU - DAL
Food
Crew
Entertainment
Overall
Boarding
Comfort
Reviews
Ila,Mar 2025
HOU - DAL
Food
Crew
Entertainment
Overall
Boarding
Comfort
Reviews
Ila,Mar 2025
HOU - DAL
Food
Crew
Entertainment
Overall
Boarding
Comfort
Reviews
Ila,Mar 2025
HOU - DAL
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$38 | Average$89 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$179 | Average$341 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$191 | Average$406 | FlexibilityNo cancel fee | On-time63% | |
Cheapest$217 | Average$358 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$218 | Average$389 | FlexibilityNo cancel fee | On-time69% |