Flights from Chicago Midway International Airport to Portland (PDX)
Plane tickets Chicago Midway International Airport – Portland
Looking for affordable flights from Chicago Midway International Airport to Portland? Our site offers the best prices and a convenient search to plan your ideal trip. Book now and start your adventure without extra costs or hassle!
See also:
- Flights from Portland to Chicago Midway International Airport for the return trip
- Flights from Chicago Midway International Airport to any destination
- Fares from Portland to any destination
- Flights from United States to any destination
- Prices for flights to Chicago Midway International Airport
- Cheap tickets to United States
- Find flights from Chicago to United States
- Flights from Portland to United States
- Flights from United States to United States
- Cheap flights from Portland to Chicago
- Cheap flights from Chicago to Portland
Flight schedule Chicago Midway International Airport Portland 2026
| Departure | Arrival | Duration | Flight | Days of week |
|---|---|---|---|---|
| 05:15 (MDW) | 12:35 (PDX) | 9 h 20 min | Southwest Airlines (WN 738) |
|
| 09:45 (MDW) | 12:10 (PDX) | 4 h 25 min | Southwest Airlines (WN 2217) |
|
| 10:05 (MDW) | 12:30 (PDX) | 4 h 25 min | Southwest Airlines (WN 4707) |
|
| 11:00 (MDW) | 13:25 (PDX) | 4 h 25 min | Southwest Airlines (WN 1978) |
|
| 15:40 (MDW) | 21:00 (PDX) | 7 h 20 min | Southwest Airlines (WN 1048) |
|
| 20:40 (MDW) | 23:10 (PDX) | 4 h 30 min | Southwest Airlines (WN 2950) |
|
| 21:15 (MDW) | 23:55 (PDX) | 4 h 40 min | Southwest Airlines (WN 3295) |
|
| 21:45 (MDW) | 00:15 (PDX) +1 day | 4 h 30 min | Southwest Airlines (WN 2950) |
|
Flights from Chicago Midway International Airport to United States
Below are the most popular routes from Chicago Midway International Airport to United States, sorted by the lowest available fares for different travel dates with no commission.
Frontier Airlines
F9 2144
18:42
Chicago Midway International Airport
13.11.2026
2h 11m
Direct flight
21:53
Atlanta
13.11.2026
from $55
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Frontier Airlines
F9 2292
06:08
Chicago Midway International Airport
11.11.2026
7h 31m
with 1 stop
14:39
Fort Lauderdale
11.11.2026
from $55
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Southwest Airlines
WN 2339
20:45
Chicago Midway International Airport
16.11.2026
1h 15m
Direct flight
22:00
St Louis
16.11.2026
from $55
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Southwest Airlines
WN 1288
10:15
Chicago Midway International Airport
18.11.2026
1h 40m
Direct flight
11:55
Memphis
18.11.2026
from $65
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Frontier Airlines
F9 2292
06:08
Chicago Midway International Airport
10.11.2026
10h 4m
with 1 stop
17:12
Washington
10.11.2026
from $66
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Flights from other airports to Portland
The cheapest flights from other airports to Portland with no commission.
Turkish Airlines
TK 420
07:55
Vnukovo Airport
03.12.2026
26h 36m
with 2 stops
23:31
Portland
03.12.2026
from $735
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Alaska Airlines
AS 1461
11:28
Sacramento International Airport
02.11.2026
1h 34m
Direct flight
13:02
Portland
02.11.2026
from $140
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Air Canada
AC 26
17:35
Shanghai Pudong International Airport
11.11.2026
13h 6m
with 1 stop
14:41
Portland
11.11.2026
from $460
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Frontier Airlines
F9 689
18:00
Ronald Reagan National Airport
02.11.2026
20h 7m
with 1 stop
11:07
Portland
03.11.2026
from $250
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Frequently asked questions about the route Chicago Midway International Airport – Portland
How much does a flight from Chicago Midway International Airport to Portland cost?
Flight prices from Chicago Midway International Airport to Portland vary by season, day of week, and booking time. For current fares and the best deals, use our search tool to see all options and prices. The lowest fare is $251.
Which airlines fly from Chicago Midway International Airport to Portland?
The following airlines operate the route Chicago Midway International Airport — Portland: Southwest Airlines, Delta.
How long is the flight from Chicago Midway International Airport to Portland?
The fastest scheduled nonstop flight from Chicago Midway International Airport to Portland takes about 4 hours and 25 minutes.
Is there a direct flight Chicago Midway International Airport — Portland?
The schedule data currently available to us includes nonstop flights from Chicago Midway International Airport to Portland. Airlines such as Southwest Airlines operate these flights. Use our search to check options for your dates.
How often do flights operate from Chicago Midway International Airport to Portland?
There are at least 1 flight per day on the route Chicago Midway International Airport — Portland from various airlines. Schedules change by season and day of week. Use our search for the latest schedule and availability.
