
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Portland (PDX). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $357 (Southwest) |
One-way from | $184 (Southwest) |
Popular in | October |
Cheapest in | September |
Average price | $371 |
Good round-trip deal | $360 or less |
Good one-way deal | $248 or less |
Fly from
Fly to
Route
Depart
Return
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Sat 1/9
8:45 am-5:35 pm
1 stop10h 50m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Tue 3/9
5:20 am-1:05 pm
2 stops9h 45m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Wed 12/23
9:30 pm-12:15 am
Nonstop4h 45m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Sat 12/12
9:37 am-6:54 pm
2 stops11h 17m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Fri 2/12
9:35 pm-12:15 am
Nonstop4h 40m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Sun 12/13
9:15 pm-11:55 pm
Nonstop4h 40m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Sat 12/5
10:20 am-5:45 pm
1 stop9h 25m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Sat 12/5
9:37 am-5:19 pm
2 stops9h 42m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Wed 12/2
8:40 pm-11:25 pm
Nonstop4h 45m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Wed 12/9
10:24 am-6:58 pm
2 stops10h 34m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
Everything you need to know about your flight from Chicago Midway Airport to Portland
Comfort
Boarding
Crew
Food
Overall
Entertainment
Reviews
Patricia,Oct 2026
DAL - TPA
Comfort
Boarding
Crew
Food
Overall
Entertainment
Reviews
Patricia,Oct 2026
DAL - TPA
Find useful and relevant information for your journey from Midway to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$239 | Average$374 | FlexibilityNo cancel fee | On-time63% |