
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $229 (Southwest) |
One-way from | $115 (Delta) |
Popular in | April |
Cheapest in | September |
Average price | $264 |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoPortland
MDW - PWM
MDWPWM
Chicago Midway
Tue 1/13
6:50 am-12:10 pm
1 stop4h 20m
Portland
Wed 1/14
5:45 am-1:55 pm
2 stops9h 10m
ChicagoPortland
MDW - PWM
MDWPWM
Chicago Midway
Sat 1/10
9:32 am-10:27 pm
2 stops11h 55m
Portland
Sat 1/17
6:00 am-12:48 pm
2 stops7h 48m
ChicagoPortland
MDW - PWM
MDWPWM
Chicago Midway
Fri 1/23
12:48 pm-11:22 pm
2 stops9h 34m
Portland
Mon 1/26
2:35 pm-10:22 pm
2 stops8h 47m
ChicagoPortland
MDW - PWM
MDWPWM
Chicago Midway
Tue 1/13
1:28 pm-11:22 pm
2 stops8h 54m
Portland
Wed 1/14
12:20 pm-5:34 pm
1 stop6h 14m
ChicagoPortland
MDW - PWM
MDWPWM
Chicago Midway
Mon 3/23
9:32 am-4:10 pm
1 stop5h 38m
Portland
Thu 3/26
12:50 pm-5:55 pm
1 stop6h 05m
ChicagoPortland
MDW - PWM
MDWPWM
Chicago Midway
Mon 3/23
4:05 pm-12:05 am
2 stops7h 00m
Portland
Thu 3/26
5:30 pm-11:35 pm
1 stop7h 05m
ChicagoPortland
MDW - PWM
MDWPWM
Chicago Midway
Tue 12/23
5:25 pm-12:05 am
2 stops5h 40m
Portland
Sat 1/3
5:15 am-8:55 am
1 stop4h 40m
ChicagoPortland
MDW - PWM
MDWPWM
Chicago Midway
Fri 3/20
6:35 am-11:55 am
1 stop4h 20m
Portland
Mon 3/23
5:30 pm-11:35 pm
1 stop7h 05m
ChicagoPortland
MDW - PWM
MDWPWM
Chicago Midway
Sun 1/4
12:45 pm-12:20 am
2 stops10h 35m
Portland
Sat 1/10
6:00 am-4:16 pm
2 stops11h 16m
ChicagoPortland
MDW - PWM
MDWPWM
Chicago Midway
Sat 3/28
9:32 am-4:10 pm
1 stop5h 38m
Portland
Fri 4/3
12:50 pm-5:55 pm
1 stop6h 05m
| 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 |
Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Portland, Maine (average of $92). Flying from Chicago Midway Airport to Portland, Maine in April is currently the most expensive (average of $188). 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 typically best to fly out from Chicago Midway Airport to Portland, Maine in the afternoon. Doing so could potentially save you 55% on the flight price compared to flying in the evening, which is usually more expensive.
About 8% of weekly flights between Chicago and Portland have experienced delays in the past year, with the average delay time being 93 minutes.
Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.
Wednesday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.
Over the last year, Southwest have had the lowest number of delays on this route, with just 6% of flights being delayed.
Food
Comfort
Crew
Entertainment
Overall
Boarding
Reviews
Thomas,Dec 2025
SEA - DEN
Food
Comfort
Crew
Entertainment
Overall
Boarding
Reviews
Thomas,Dec 2025
SEA - DEN
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$313 | Average$411 | FlexibilityNo cancel fee | On-time63% |