Expect security wait times up to 15 minutes off-peak, longer during rush hours. Use Express Lanes if eligible for faster processing.
Round-trip from | $218 (Southwest) |
---|---|
One-way from | $102 (Trip.com) |
Popular in | December |
Cheapest in | February |
Average price | $442 |
Good round-trip deal | $320 or less |
Good one-way deal | $200 or less |
Fly from
Fly to
Route
Depart
Return
Price
PortlandChicago
PDX - MDW
PDXMDW
Portland
Sat 8/23
6:50 am-4:35 pm
2 stops7h 45m
Chicago Midway
Sat 8/30
8:20 am-10:35 am
Nonstop4h 15m
PortlandChicago
PDX - MDW
PDXMDW
Portland
Fri 8/22
12:46 am-8:51 am
1 stop6h 05m
Chicago Midway
Sat 8/30
7:17 pm-11:31 pm
1 stop6h 14m
PortlandChicago
PDX - MDW
PDXMDW
Portland
Fri 8/1
5:50 pm-8:54 pm
1 stop25h 04m
Chicago Midway
Mon 8/11
12:35 pm-11:30 am
1 stop24h 55m
PortlandChicago
PDX - MDW
PDXMDW
Portland
Sat 7/19
6:35 am-8:54 pm
1 stop12h 19m
PortlandChicago
PDX - MDW
PDXMDW
Portland
Wed 9/10
6:00 am-12:00 pm
Nonstop4h 00m
PortlandChicago
PDX - MDW
PDXMDW
Portland
Fri 8/1
12:40 am-8:45 am
1 stop6h 05m
Currently, April is the cheapest month in which you can book a flight from Portland to Chicago Midway Airport (average of $160). Flying from Portland to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 Portland to Chicago Midway Airport in the afternoon. Doing so could potentially save you 38% on the flight price compared to flying in the morning, which is usually more expensive.
Overall
Comfort
Food
Crew
Boarding
Entertainment
Reviews
John,May 2025
PVD - BNA
Overall
Comfort
Food
Crew
Boarding
Entertainment
Reviews
John,May 2025
PVD - BNA
Overall
Comfort
Food
Crew
Boarding
Entertainment
Reviews
John,May 2025
PVD - BNA
Overall
Comfort
Food
Crew
Boarding
Entertainment
Reviews
John,May 2025
PVD - BNA
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Cheapest$108 | Average$288 | FlexibilityNo cancel fee | On-time62% | |
Cheapest$249 | Average$434 | FlexibilityNo cancel fee | On-time63% |