$169+ Cheap flights from Portland (PDX) to Midway (MDW)
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 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MDW
Aug 23 — Aug 301
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Midway 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 Portland to Midway
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Cheapest flights from Portland to MidwayExplore the most affordable flight options available from Portland to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 24, 2026.
Explore the most affordable flight options available from Portland to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 24, 2026.
This Southwest deal was found by Cheapflights users on 7/21. 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 8/266:55 am
PDX
- MDW
1 stop7h 05m
Southwest
Wed 9/910:30 am
MDW
- PDX
2 stops9h 20m
Southwest
Deal found 7/21![Southwest logo]()
$322
This Southwest deal was found by Cheapflights users on 7/21. 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 9/95:50 am
PDX
- MDW
2 stops8h 45m
Southwest
Tue 9/1511:10 am
MDW
- PDX
2 stops8h 35m
Southwest
Deal found 7/21![Southwest logo]()
$323
This Southwest deal was found by Cheapflights users on 7/20. 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 8/2211:20 am
PDX
- MDW
2 stops8h 55m
Southwest
Sat 8/292:15 pm
MDW
- PDX
2 stops9h 05m
Southwest
Deal found 7/20![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 7/21. 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 9/1012:40 pm
PDX
- MDW
2 stops9h 05m
Southwest
Tue 9/158:55 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 7/21![Southwest logo]()
$328
This Southwest deal was found by Cheapflights users on 7/21. 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 8/2011:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Fri 8/286:15 am
MDW
- PDX
2 stops10h 30m
Southwest
Deal found 7/21![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 7/20. 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 8/255:50 am
PDX
- MDW
2 stops8h 45m
Southwest
Fri 8/2810:15 am
MDW
- PDX
2 stops10h 10m
Southwest
Deal found 7/20![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 7/21. 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 9/1011:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Sun 9/135:40 am
MDW
- PDX
1 stop7h 40m
Southwest
Deal found 7/21![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 7/21. 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 10/15:20 am
PDX
- MDW
Nonstop3h 50m
Southwest
Mon 10/55:15 am
MDW
- PDX
2 stops9h 20m
Southwest
Deal found 7/21![Southwest logo]()
$338
This Southwest deal was found by Cheapflights users on 7/21. 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 8/145:45 am
PDX
- MDW
2 stops9h 35m
Southwest
Mon 8/178:50 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 7/21![Southwest logo]()
$342
This Southwest deal was found by Cheapflights users on 7/21. 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 9/295:50 am
PDX
- MDW
2 stops8h 45m
Southwest
Fri 10/23:45 pm
MDW
- PDX
2 stops10h 45m
Southwest
Deal found 7/21![Southwest logo]()
$343
This Delta deal was found by Cheapflights users on 7/21. 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.
Thu 8/2712:35 am
PDX
- MDW
1 stop6h 04m
Delta
Fri 9/1111:35 am
MDW
- PDX
1 stop9h 24m
Delta
Deal found 7/21![Delta logo]()
$347
This Southwest deal was found by Cheapflights users on 7/21. 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 8/153:50 pm
PDX
- MDW
1 stop12h 00m
Southwest
Fri 8/215:00 pm
MDW
- PDX
2 stops8h 40m
Southwest
Deal found 7/21![Southwest logo]()
$348
Best flights from Portland to MidwayDiscover carefully curated flight deals from Portland to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 24, 2026.
Discover carefully curated flight deals from Portland to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 24, 2026.
This Southwest deal was found by Cheapflights users on 7/21. 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 9/411:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Fri 9/119:00 am
MDW
- PDX
1 stop8h 00m
Southwest
Deal found 7/21![Southwest logo]()
$323
This Delta deal was found by Cheapflights users on 7/21. 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 9/912:25 am
PDX
- MDW
1 stop6h 23m
Delta
Mon 9/147:13 pm
MDW
- PDX
1 stop5h 57m
Delta
Deal found 7/21![Delta logo]()
$347
This Southwest deal was found by Cheapflights users on 7/20. 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 8/2211:20 am
PDX
- MDW
2 stops8h 55m
Southwest
Sat 8/292:15 pm
MDW
- PDX
2 stops9h 05m
Southwest
Deal found 7/20![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 7/18. 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.
Mon 9/286:25 am
PDX
- MDW
2 stops8h 40m
Southwest
Fri 10/29:45 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 7/18![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 7/19. 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 9/235:50 am
PDX
- MDW
2 stops8h 45m
Southwest
Fri 9/256:15 am
MDW
- PDX
2 stops10h 30m
Southwest
Deal found 7/19![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 7/18. 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 8/215:45 am
PDX
- MDW
2 stops9h 35m
Southwest
Tue 8/2510:30 am
MDW
- PDX
2 stops9h 20m
Southwest
Deal found 7/18![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 7/21. 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 8/153:50 pm
PDX
- MDW
1 stop12h 00m
Southwest
Fri 8/215:00 pm
MDW
- PDX
2 stops8h 40m
Southwest
Deal found 7/21![Southwest logo]()
$348
This Southwest deal was found by Cheapflights users on 7/20. 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 8/2012:40 pm
PDX
- MDW
2 stops9h 05m
Southwest
Sat 8/226:00 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 7/20![Southwest logo]()
$352
This Southwest deal was found by Cheapflights users on 7/20. 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 8/2012:40 pm
PDX
- MDW
2 stops9h 05m
Southwest
Mon 8/245:30 am
MDW
- PDX
1 stop6h 45m
Southwest
Deal found 7/20![Southwest logo]()
$358
This Southwest deal was found by Cheapflights users on 7/19. 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 10/281:10 pm
PDX
- MDW
2 stops8h 35m
Southwest
Sun 11/15:45 am
MDW
- PDX
1 stop7h 40m
Southwest
Deal found 7/19![Southwest logo]()
$368
This Southwest deal was found by Cheapflights users on 7/18. 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 9/412:40 pm
PDX
- MDW
2 stops9h 05m
Southwest
Tue 9/86:00 pm
MDW
- PDX
1 stop6h 15m
Southwest
Deal found 7/18![Southwest logo]()
$374
This Southwest deal was found by Cheapflights users on 7/23. 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.
Sat 8/1511:40 am
PDX
- MDW
1 stop5h 25m
Southwest
Sat 8/225:40 am
MDW
- PDX
1 stop9h 10m
Southwest
Deal found 7/23![Southwest logo]()
$377
Last-minute flights from Portland to MidwayDiscover last-minute flight deals from Portland to Midway. Data last updated July 24, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Midway. Data last updated July 24, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/19. 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 8/116:30 pm
PDX
- MDW
1 stop9h 15m
Southwest
Tue 8/188:55 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 7/19![Southwest logo]()
$351
This Southwest deal was found by Cheapflights users on 7/21. 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 8/145:45 am
PDX
- MDW
2 stops9h 35m
Southwest
Mon 8/178:50 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 7/21![Southwest logo]()
$342
This Southwest deal was found by Cheapflights users on 7/21. 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 8/153:50 pm
PDX
- MDW
1 stop12h 00m
Southwest
Fri 8/215:00 pm
MDW
- PDX
2 stops8h 40m
Southwest
Deal found 7/21![Southwest logo]()
$348
This Southwest deal was found by Cheapflights users on 7/22. 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 8/197:05 am
PDX
- MDW
2 stops8h 05m
Southwest
Tue 8/2512:00 pm
MDW
- PDX
2 stops9h 50m
Southwest
Deal found 7/22![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 7/21. 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 8/2011:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Fri 8/289:00 am
MDW
- PDX
1 stop8h 00m
Southwest
Deal found 7/21![Southwest logo]()
$323
This Southwest deal was found by Cheapflights users on 7/21. 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 8/2011:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Tue 8/2510:05 am
MDW
- PDX
1 stop7h 15m
Southwest
Deal found 7/21![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 7/20. 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.
Mon 8/245:45 am
PDX
- MDW
2 stops9h 35m
Southwest
Mon 8/319:00 am
MDW
- PDX
1 stop8h 00m
Southwest
Deal found 7/20![Southwest logo]()
$338
This Southwest deal was found by Cheapflights users on 7/20. 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 8/255:50 am
PDX
- MDW
2 stops8h 45m
Southwest
Fri 8/2810:15 am
MDW
- PDX
2 stops10h 10m
Southwest
Deal found 7/20![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 7/21. 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 8/266:55 am
PDX
- MDW
1 stop7h 05m
Southwest
Wed 9/910:30 am
MDW
- PDX
2 stops9h 20m
Southwest
Deal found 7/21![Southwest logo]()
$322
This Delta deal was found by Cheapflights users on 7/21. 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.
Thu 8/2712:35 am
PDX
- MDW
1 stop6h 04m
Delta
Fri 9/1111:35 am
MDW
- PDX
1 stop9h 24m
Delta
Deal found 7/21![Delta logo]()
$347
This Southwest deal was found by Cheapflights users on 7/20. 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 8/2812:40 pm
PDX
- MDW
2 stops9h 05m
Southwest
Mon 8/318:50 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 7/20![Southwest logo]()
$328
One-way flights from Portland to MidwaySearch for one-way flight options from Portland to Midway. Find affordable one-way fares based on user searches. Data last updated July 24, 2026.
Search for one-way flight options from Portland to Midway. Find affordable one-way fares based on user searches. Data last updated July 24, 2026.
This Southwest deal was found by Cheapflights users on 7/21. 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 9/279:15 pm
PDX
- MDW
1 stop6h 40m
Southwest
Deal found 7/21![Southwest logo]()
$169
This Southwest deal was found by Cheapflights users on 7/19. 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 8/187:05 am
PDX
- MDW
2 stops8h 05m
Southwest
Deal found 7/19![Southwest logo]()
$174
This Southwest deal was found by Cheapflights users on 7/22. 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 8/1911:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 7/22![Southwest logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 7/19. 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.
Tue 10/205:35 pm
PDX
- MDW
2 stops26h 23m
Frontier
Deal found 7/19![Frontier logo]()
$183
This Southwest deal was found by Cheapflights users on 7/23. 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 8/278:00 am
PDX
- MDW
1 stop7h 00m
Southwest
Deal found 7/23![Southwest logo]()
$184
This Southwest deal was found by Cheapflights users on 7/22. 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 8/201:35 pm
PDX
- MDW
1 stop8h 10m
Southwest
Deal found 7/22![Southwest logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
Sat 8/225:56 pm
PDX
- MDW
2 stops14h 59m
Frontier
Deal found 7/20![Frontier logo]()
$191
This Southwest deal was found by Cheapflights users on 7/20. 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.
Mon 9/711:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 7/20![Southwest logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
Fri 8/2112:20 pm
PDX
- MDW
2 stops20h 30m
Frontier
Deal found 7/20![Frontier logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 7/19. 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.
Mon 10/1912:34 pm
PDX
- MDW
2 stops31h 24m
Frontier
Deal found 7/19![Frontier logo]()
$196
This Southwest deal was found by Cheapflights users on 7/22. 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 8/216:15 am
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 7/22![Southwest logo]()
$200
Find flight deals from Portland to Midway
Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to Midway (MDW). 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 July 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $322 (Southwest) |
One-way from | $169 (Southwest) |
Popular in | March |
Cheapest in | January |
Average price | $375 |
Good round-trip deal | $368 or less |
Good one-way deal | $214 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to Midway 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 2,558,603 searches. Data last updated July 24, 2026.
Use the filters below to find and compare flights from Portland to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
PortlandChicago
PDX - MDW
PDXMDW
Portland
Fri 9/4
11:30 pm-5:25 am
Nonstop3h 55m
Chicago Midway
Fri 9/11
9:00 am-3:00 pm
1 stop8h 00m
$323
PortlandChicago
PDX - MDW
PDXMDW
Portland
Sat 8/22
11:20 am-10:15 pm
2 stops8h 55m
Chicago Midway
Sat 8/29
2:15 pm-9:20 pm
2 stops9h 05m
$327
PortlandChicago
PDX - MDW
PDXMDW
Portland
Mon 9/28
6:25 am-5:05 pm
2 stops8h 40m
Chicago Midway
Fri 10/2
9:45 pm-12:10 am
Nonstop4h 25m
$332
PortlandChicago
PDX - MDW
PDXMDW
Portland
Wed 9/23
5:50 am-4:35 pm
2 stops8h 45m
Chicago Midway
Fri 9/25
6:15 am-2:45 pm
2 stops10h 30m
$333
PortlandChicago
PDX - MDW
PDXMDW
Portland
Fri 8/21
5:45 am-5:20 pm
2 stops9h 35m
Chicago Midway
Tue 8/25
10:30 am-5:50 pm
2 stops9h 20m
$337
PortlandChicago
PDX - MDW
PDXMDW
Portland
Wed 9/9
12:25 am-8:48 am
1 stop6h 23m
Chicago Midway
Mon 9/14
7:13 pm-11:10 pm
1 stop5h 57m
$347
PortlandChicago
PDX - MDW
PDXMDW
Portland
Sat 8/15
3:50 pm-5:50 am
1 stop12h 00m
Chicago Midway
Fri 8/21
5:00 pm-11:40 pm
2 stops8h 40m
$348
PortlandChicago
PDX - MDW
PDXMDW
Portland
Thu 8/20
12:40 pm-11:45 pm
2 stops9h 05m
Chicago Midway
Sat 8/22
6:00 pm-8:15 pm
Nonstop4h 15m
$352
PortlandChicago
PDX - MDW
PDXMDW
Portland
Thu 8/20
12:40 pm-11:45 pm
2 stops9h 05m
Chicago Midway
Mon 8/24
5:30 am-10:15 am
1 stop6h 45m
$358
PortlandChicago
PDX - MDW
PDXMDW
Portland
Wed 10/28
1:10 pm-11:45 pm
2 stops8h 35m
Chicago Midway
Sun 11/1
5:45 am-11:25 am
1 stop7h 40m
$368
Showing 1-10 of 23 resultsSorted by cheapest first
Compare providers for flights from Portland to Midway
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 Portland to Midway in July.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Portland-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Portland-Chicago Midway Airport 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 Portland-Chicago Midway Airport 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 Portland to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Portland with our price prediction graph.
PDX-MDW
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 Portland to Chicago Midway Airport
Prices
Airlines
What is the cheapest month to book a flight from Portland to Chicago Midway Airport?
Currently, January is the cheapest month in which you can book a flight from Portland to Chicago Midway Airport (average of $197). Flying from Portland to Chicago Midway Airport in March is currently the most expensive (average of $386). 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 PDX to MDW?
Find hourly flight availability from Portland to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 24, 2026.
It’s typically best to fly out from Portland to Chicago Midway Airport at noon. Doing so could potentially save you 19% on the flight price compared to flying in the morning, which is usually more expensive.
The best insider tips for Portland to Chicago Midway Airport 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 Portland to Chicago Midway Airport trip
Our travel experts
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated July 24, 2026.
Read reviews from past customers who have flown Southwest from Portland to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Portland to Midway. 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 Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on July 24, 2026.
Portland and Midway flights
Browse other Portland and Midway flight options. Last updated on July 24, 2026.
Other flights from Portland
Browse through other flights departing from Portland. Flights are based on user searches made on Cheapflights and were last updated on July 24, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Portland to Midway
Discover the top airline that operate flights from Portland to Midway. 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 2,558,603 searches. Data last updated July 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$227 | Average$356 | FlexibilityNo cancel fee | On-time63% |