Most accurate provider | FlightHub 3 stars |
---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $219 (American Airlines) |
One-way from | $90 (United Airlines) |
Popular in | November |
Cheapest in | September |
Average price | $389 |
Good round-trip deal | $376 or less |
Good one-way deal | $195 or less |
Fly from
Fly to
Route
Depart
Return
Price
PortlandChicago
PWM - ORD
PWMORD
Portland
Thu 6/12
6:00 am-7:57 am
Nonstop2h 57m
Chicago O'Hare Intl
Sun 6/15
8:35 am-5:11 pm
1 stop7h 36m
PortlandChicago
PWM - MDW
PWMMDW
Portland
Fri 5/2
4:40 pm-8:05 pm
1 stop4h 25m
Chicago Midway
Sun 5/4
6:55 am-2:25 pm
1 stop6h 30m
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 5/9
3:35 pm-9:54 pm
1 stop7h 19m
Chicago O'Hare Intl
Sun 5/11
6:15 am-2:40 pm
1 stop7h 25m
PortlandChicago
PWM - ORD
PWMORD
Portland
Fri 5/9
9:30 pm-11:32 pm
1 stop27h 02m
Chicago O'Hare Intl
Sun 5/11
4:15 pm-8:40 pm
1 stop27h 25m
PortlandChicago
PWM - ORD
PWMORD
Portland
Wed 5/28
1:40 pm-7:20 pm
1 stop6h 40m
Chicago O'Hare Intl
Tue 6/3
1:45 pm-11:21 pm
2 stops8h 36m
PortlandChicago
PWM - ORD
PWMORD
Portland
Mon 6/9
5:40 am-1:05 pm
1 stop8h 25m
Chicago O'Hare Intl
Wed 6/11
1:50 pm-11:25 pm
1 stop8h 35m
PortlandChicago
PWM - ORD
PWMORD
Portland
Thu 5/8
6:13 am-8:05 am
Nonstop2h 52m
Chicago O'Hare Intl
Thu 5/8
5:55 pm-11:59 pm
1 stop5h 04m
PortlandChicago
PWM - MDW
PWMMDW
Portland
Sat 5/3
7:00 am-12:35 pm
1 stop6h 35m
Chicago Midway
Tue 5/6
9:20 am-4:03 pm
1 stop5h 43m
PortlandChicago
PWM - ORD
PWMORD
Portland
Sat 5/24
4:43 pm-6:40 pm
Nonstop2h 57m
PortlandChicago
PWM - ORD
PWMORD
Portland
Tue 4/29
6:35 am-12:26 pm
1 stop6h 51m
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 | |
Price Accuracy1 star | Trust Score*3 stars |
Booking 65 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland, Maine to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Currently, August is the cheapest month in which you can book a flight from Portland, Maine to Chicago (average of $245). Flying from Portland, Maine to Chicago in March is currently the most expensive (average of $323). 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 Portland, Maine to Chicago is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 77% on airfare.
Travelers seeking maximum savings on their Portland, Maine to Chicago flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.
If weather is an important factor for your trip to Chicago, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
Boarding
Overall
Crew
Food
Entertainment
Comfort
Reviews
Ila,Mar 2025
HOU - DAL
Boarding
Overall
Crew
Food
Entertainment
Comfort
Reviews
Ila,Mar 2025
HOU - DAL
Boarding
Overall
Crew
Food
Entertainment
Comfort
Reviews
Ila,Mar 2025
HOU - DAL
Boarding
Overall
Crew
Food
Entertainment
Comfort
Reviews
Ila,Mar 2025
HOU - DAL
Boarding
Overall
Crew
Food
Entertainment
Comfort
Reviews
Ila,Mar 2025
HOU - DAL
Boarding
Overall
Crew
Food
Entertainment
Comfort
Reviews
Ila,Mar 2025
HOU - DAL
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$38 | Average$109 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$158 | Average$327 | FlexibilityNo cancel fee | On-time71% | |
Cheapest$189 | Average$361 | FlexibilityNo cancel fee | On-timeN/A | |
Cheapest$193 | Average$400 | FlexibilityNo cancel fee | On-time69% | |
Cheapest$281 | Average$390 | FlexibilityNo cancel fee | On-time63% |