$179+ Cheap flights from Midway (MDW) to Portland (PDX)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/12. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PDX
Sep 27 — Oct 41
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Midway to Portland with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Midway to Portland
Cheapest
Best
Last-minute
One-way
Cheapest flights from Midway to PortlandExplore the most affordable flight options available from Midway to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 28, 2026.
Explore the most affordable flight options available from Midway to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 28, 2026.
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/99:45 pm -
Nonstop4h 25m
Fri 10/1611:35 pm -
Nonstop3h 50m
Deal found 8/25![Southwest logo]()
$357
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/99:45 pm -
Nonstop4h 30m
Tue 10/1311:35 pm -
Nonstop3h 50m
Deal found 8/27![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:50 pm -
Nonstop4h 20m
Mon 9/2112:40 pm -
2 stops9h 10m
Deal found 8/27![Southwest logo]()
$368
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/63:40 pm -
1 stop7h 20m
Mon 11/911:30 pm -
Nonstop3h 45m
Deal found 8/27![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/99:45 pm -
Nonstop4h 25m
Mon 10/125:20 am -
Nonstop3h 50m
Deal found 8/25![Southwest logo]()
$376
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/19:45 pm -
Nonstop4h 25m
Fri 10/23:30 pm -
1 stop7h 35m
Deal found 8/27![Southwest logo]()
$377
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/299:45 am -
Nonstop4h 25m
Sun 11/17:35 am -
2 stops8h 00m
Deal found 8/27![Southwest logo]()
$378
This Southwest deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:15 am -
2 stops9h 20m
Tue 11/36:55 am -
2 stops8h 25m
Deal found 8/28![Southwest logo]()
$383
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:15 pm -
1 stop9h 05m
Sun 10/185:20 am -
Nonstop3h 50m
Deal found 8/25![Southwest logo]()
$386
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:25 am -
1 stop9h 10m
Sun 10/47:35 pm -
1 stop8h 10m
Deal found 8/27![Southwest logo]()
$387
Best flights from Midway to PortlandDiscover carefully curated flight deals from Midway to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 28, 2026.
Discover carefully curated flight deals from Midway to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 28, 2026.
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/29:45 pm -
Nonstop4h 25m
Mon 10/511:35 pm -
Nonstop3h 50m
Deal found 8/24![Southwest logo]()
$357
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2110:59 am -
1 stop10h 10m
Sat 10/2411:52 am -
1 stop8h 41m
Deal found 8/28![Delta logo]()
$377
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/37:15 pm -
Nonstop4h 25m
Tue 10/611:35 pm -
Nonstop3h 50m
Deal found 8/27![Southwest logo]()
$357
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:13 pm -
1 stop5h 57m
Thu 10/111:10 pm -
1 stop7h 57m
Deal found 8/23![Delta logo]()
$377
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:15 pm -
Nonstop4h 25m
Tue 10/1311:35 pm -
Nonstop3h 50m
Deal found 8/25![Southwest logo]()
$357
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/299:45 am -
Nonstop4h 25m
Sun 11/111:30 pm -
Nonstop3h 45m
Deal found 8/25![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:50 pm -
Nonstop4h 20m
Wed 9/235:50 am -
2 stops8h 45m
Deal found 8/25![Southwest logo]()
$368
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/208:40 pm -
Nonstop4h 25m
Fri 10/302:55 pm -
2 stops8h 15m
Deal found 8/24![Southwest logo]()
$372
This Southwest deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/410:15 am -
2 stops9h 50m
Sun 11/811:30 pm -
Nonstop3h 45m
Deal found 8/28![Southwest logo]()
$382
This Southwest deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:15 am -
2 stops9h 20m
Tue 11/36:55 am -
2 stops8h 25m
Deal found 8/28![Southwest logo]()
$383
Last-minute flights from Midway to PortlandDiscover last-minute flight deals from Midway to Portland. Data last updated August 28, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Portland. Data last updated August 28, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:30 pm -
Nonstop4h 15m
Sun 9/1311:30 pm -
Nonstop3h 55m
Deal found 8/23![Southwest logo]()
$383
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:50 pm -
Nonstop4h 20m
Mon 9/2112:40 pm -
2 stops9h 10m
Deal found 8/27![Southwest logo]()
$368
This Southwest deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/205:40 am -
1 stop7h 40m
Wed 9/235:50 am -
2 stops8h 45m
Deal found 8/28![Southwest logo]()
$388
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/228:55 pm -
Nonstop4h 20m
Tue 9/2911:30 pm -
Nonstop3h 55m
Deal found 8/25![Southwest logo]()
$357
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:50 am -
2 stops10h 35m
Thu 9/2411:30 pm -
Nonstop3h 55m
Deal found 8/25![Southwest logo]()
$372
This Southwest deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:30 pm -
Nonstop4h 15m
Thu 10/15:20 am -
Nonstop3h 50m
Deal found 8/26![Southwest logo]()
$376
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/258:50 pm -
Nonstop4h 20m
Mon 9/287:55 pm -
1 stop7h 05m
Deal found 8/27![Southwest logo]()
$377
This Southwest deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/262:15 pm -
2 stops9h 10m
Sat 10/32:40 pm -
1 stop6h 25m
Deal found 8/28![Southwest logo]()
$382
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:13 pm -
1 stop5h 57m
Fri 10/28:44 pm -
2 stops10h 04m
Deal found 8/28![Delta logo]()
$392
One-way flights from Midway to PortlandSearch for one-way flight options from Midway to Portland. Find affordable one-way fares based on user searches. Data last updated August 28, 2026.
Search for one-way flight options from Midway to Portland. Find affordable one-way fares based on user searches. Data last updated August 28, 2026.
This Southwest deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2610:15 am -
Nonstop4h 15m
Deal found 8/28![Southwest logo]()
$179
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:15 am -
2 stops9h 20m
Deal found 8/27![Southwest logo]()
$189
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:05 am -
2 stops13h 26m
Deal found 8/27![Delta logo]()
$194
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/249:25 pm -
Nonstop4h 40m
Deal found 8/25![Southwest logo]()
$195
This Southwest deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:15 pm -
1 stop7h 05m
Deal found 8/26![Southwest logo]()
$199
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2312:49 pm -
2 stops12h 55m
Deal found 8/27![Delta logo]()
$204
This Southwest deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/259:25 pm -
Nonstop4h 40m
Deal found 8/28![Southwest logo]()
$205
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/275:29 pm -
1 stop6h 34m
Deal found 8/28![Delta logo]()
$208
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1412:15 pm -
2 stops9h 55m
Deal found 8/23![Southwest logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/151:12 pm -
2 stops22h 59m
Deal found 8/26![Frontier logo]()
$211
This Southwest deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2510:10 am -
2 stops8h 35m
Deal found 8/25![Southwest logo]()
$213
This Southwest deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/68:35 pm -
Nonstop4h 15m
Deal found 8/28![Southwest logo]()
$215
Find flight deals from Midway to Portland
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 August 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $357 (Southwest) |
One-way from | $179 (Southwest) |
Popular in | October |
Cheapest in | March |
Average price | $359 |
Good round-trip deal | $392 or less |
Good one-way deal | $209 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Portland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 28, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Portland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Fri 10/2
9:45 pm-12:10 am
Nonstop4h 25m
Portland
Mon 10/5
11:35 pm-5:25 am
Nonstop3h 50m
$357
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Sat 10/3
7:15 pm-9:40 pm
Nonstop4h 25m
Portland
Tue 10/6
11:35 pm-5:25 am
Nonstop3h 50m
$357
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Sat 10/10
7:15 pm-9:40 pm
Nonstop4h 25m
Portland
Tue 10/13
11:35 pm-5:25 am
Nonstop3h 50m
$357
Quickest round-trip
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Thu 10/29
9:45 am-12:10 pm
Nonstop4h 25m
Portland
Sun 11/1
11:30 pm-5:15 am
Nonstop3h 45m
$367
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Thu 9/17
8:50 pm-11:10 pm
Nonstop4h 20m
Portland
Wed 9/23
5:50 am-4:35 pm
2 stops8h 45m
$368
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Tue 10/20
8:40 pm-11:05 pm
Nonstop4h 25m
Portland
Fri 10/30
2:55 pm-1:10 am
2 stops8h 15m
$372
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Wed 10/21
10:59 am-7:09 pm
1 stop10h 10m
Portland
Sat 10/24
11:52 am-10:33 pm
1 stop8h 41m
$377
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Fri 9/25
7:13 pm-11:10 pm
1 stop5h 57m
Portland
Thu 10/1
11:10 pm-9:07 am
1 stop7h 57m
$377
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Wed 11/4
10:15 am-6:05 pm
2 stops9h 50m
Portland
Sun 11/8
11:30 pm-5:15 am
Nonstop3h 45m
$382
ChicagoPortland
MDW Chicago Midway - PDX Portland
MDWPDX
Chicago Midway
Thu 10/29
5:15 am-12:35 pm
2 stops9h 20m
Portland
Tue 11/3
6:55 am-5:20 pm
2 stops8h 25m
$383
Showing 1-10 of 20 resultsSorted by cheapest first
Compare providers for flights from Midway to Portland
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Portland in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago Midway Airport-Portland flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Portland flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Portland flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago Midway Airport-Portland flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Portland flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Midway to Portland
Have a flexible travel schedule? Discover the best time to fly to Portland from Midway with our price prediction graph.
MDW-PDX
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to Portland
What is the cheapest month to book a flight from Chicago Midway Airport to Portland?
Currently, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Portland (average of $227). Flying from Chicago Midway Airport to Portland in October is currently the most expensive (average of $538). 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.
What is the cheapest time of day to fly from MDW to PDX?
Find hourly flight availability from Midway to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 28, 2026.
One of the essential ways to save on airfare from Chicago Midway Airport to Portland is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 58% on airfare.
The best insider tips for Chicago Midway Airport to Portland flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago Midway Airport to Portland trip
Our travel experts
Reviews of airlines servicing Portland
Get insights into the airlines that provide service to Portland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Portland. Reviews last updated August 28, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to Portland, such as Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Overall
8.0
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
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.
Traveling to a place near Portland?
Book flights to Portland if you plan to visit one of these locationsBeaverton
Seaside
Lincoln City
Durham
Longview
Lake Oswego
Kelso
Clackamas
Troutdale
Vancouver
Cannon Beach
McMinnville
The Dalles
Wilsonville
Stevenson
Tillamook
Hillsboro
Astoria
Gresham
Silverton
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Midway
Popular flights
Portland flight routes
Alternative routes for Midway to Portland
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Portland by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to Portland by cabin class
Find flights from Midway to Portland, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and Portland flights
Browse other Midway and Portland flight options. Last updated on August 28, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on August 28, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to Portland
Explore flights to Portland departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 28, 2026.
Top airline flying from Midway to Portland
Discover the top airline that operate flights from Midway to Portland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$227 | Average$372 | FlexibilityNo cancel fee | On-time63% |