$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 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MDW
Aug 17 — Aug 241
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Midway with Cheapflights
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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
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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 18, 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 18, 2026.
This Delta deal was found by Cheapflights users on 7/16. 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 8/2811:20 pm
PDX
- MDW
1 stop7h 57m
Delta
Tue 9/11:51 pm
MDW
- PDX
1 stop8h 26m
Delta
Deal found 7/16![Delta logo]()
$327
This Southwest deal was found by Cheapflights users on 7/14. 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 8/218:00 am
PDX
- MDW
1 stop7h 00m
Southwest
Mon 8/249:00 am
MDW
- PDX
1 stop8h 00m
Southwest
Deal found 7/14![Southwest logo]()
$328
This Southwest deal was found by Cheapflights users on 7/16. 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 9/1411:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Fri 9/1810:25 am
MDW
- PDX
2 stops10h 35m
Southwest
Deal found 7/16![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 7/16. 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 9/51:35 pm
PDX
- MDW
2 stops12h 55m
Southwest
Tue 9/158:20 am
MDW
- PDX
2 stops8h 40m
Southwest
Deal found 7/16![Southwest logo]()
$333
This Delta deal was found by Cheapflights users on 7/16. 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.
Sun 8/3011:20 pm
PDX
- MDW
1 stop7h 57m
Delta
Fri 9/1111:35 am
MDW
- PDX
1 stop9h 24m
Delta
Deal found 7/16![Delta logo]()
$337
This Southwest deal was found by Cheapflights users on 7/17. 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 9/1112:40 pm
PDX
- MDW
2 stops9h 05m
Southwest
Sun 9/135:25 am
MDW
- PDX
1 stop7h 40m
Southwest
Deal found 7/17![Southwest logo]()
$338
This Southwest deal was found by Cheapflights users on 7/16. 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
Fri 8/216:15 pm
MDW
- PDX
1 stop7h 00m
Southwest
Deal found 7/16![Southwest logo]()
$342
This Southwest deal was found by Cheapflights users on 7/15. 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 8/1712:40 pm
PDX
- MDW
2 stops9h 05m
Southwest
Thu 8/2010:25 am
MDW
- PDX
2 stops10h 35m
Southwest
Deal found 7/15![Southwest logo]()
$343
This Southwest deal was found by Cheapflights users on 7/14. 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 8/2110:55 am
PDX
- MDW
2 stops6h 50m
Southwest
Sun 8/306:10 am
MDW
- PDX
2 stops9h 30m
Southwest
Deal found 7/14![Southwest logo]()
$347
This Southwest deal was found by Cheapflights users on 7/15. 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 8/1111:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Thu 8/138:50 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 7/15![Southwest logo]()
$351
This Southwest deal was found by Cheapflights users on 7/16. 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 8/511:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Tue 8/118:55 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 7/16![Southwest logo]()
$352
This Southwest deal was found by Cheapflights users on 7/16. 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 9/911:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Sun 9/135:40 am
MDW
- PDX
1 stop7h 40m
Southwest
Deal found 7/16![Southwest logo]()
$353
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 18, 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 18, 2026.
This Southwest deal was found by Cheapflights users on 7/15. 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 8/299:00 am
PDX
- MDW
2 stops9h 45m
Southwest
Sat 9/510:15 am
MDW
- PDX
2 stops10h 10m
Southwest
Deal found 7/15![Southwest logo]()
$327
This Delta deal was found by Cheapflights users on 7/13. 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 12/36:15 am
PDX
- MDW
1 stop8h 35m
Delta
Mon 12/141:05 pm
MDW
- PDX
1 stop11h 21m
Delta
Deal found 7/13![Delta logo]()
$377
This Southwest deal was found by Cheapflights users on 7/15. 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 8/265:50 am
PDX
- MDW
2 stops8h 45m
Southwest
Fri 8/2810:25 am
MDW
- PDX
2 stops10h 35m
Southwest
Deal found 7/15![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 7/17. 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 10/129:15 pm
PDX
- MDW
1 stop6h 30m
Southwest
Thu 10/155:15 am
MDW
- PDX
2 stops9h 20m
Southwest
Deal found 7/17![Southwest logo]()
$338
This Delta deal was found by Cheapflights users on 7/14. 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.
Tue 11/36:00 am
PDX
- MDW
1 stop8h 39m
Delta
Sat 11/76:00 am
MDW
- PDX
1 stop9h 10m
Delta
Deal found 7/14![Delta logo]()
$377
This Delta deal was found by Cheapflights users on 7/17. 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 12/310:55 pm
PDX
- MDW
1 stop7h 50m
Delta
Tue 12/812:30 pm
MDW
- PDX
1 stop9h 13m
Delta
Deal found 7/17![Delta logo]()
$392
This Southwest deal was found by Cheapflights users on 7/14. 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 11/1111:15 am
PDX
- MDW
Nonstop3h 45m
Southwest
Sun 11/156:05 pm
MDW
- PDX
1 stop8h 05m
Southwest
Deal found 7/14![Southwest logo]()
$383
This Southwest deal was found by Cheapflights users on 7/12. 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 9/186:15 am
PDX
- MDW
Nonstop3h 55m
Southwest
Sun 9/209:20 pm
MDW
- PDX
Nonstop4h 10m
Southwest
Deal found 7/12![Southwest logo]()
$389
This Southwest deal was found by Cheapflights users on 7/13. 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 8/612:40 pm
PDX
- MDW
2 stops9h 05m
Southwest
Mon 8/106:15 am
MDW
- PDX
2 stops10h 30m
Southwest
Deal found 7/13![Southwest logo]()
$428
Last-minute flights from Portland to MidwayDiscover last-minute flight deals from Portland to Midway. Data last updated July 18, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Midway. Data last updated July 18, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/16. 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 8/511:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Wed 8/198:55 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 7/16![Southwest logo]()
$352
This Southwest deal was found by Cheapflights users on 7/13. 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 8/611:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Wed 8/128:55 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 7/13![Southwest logo]()
$357
This Southwest deal was found by Cheapflights users on 7/15. 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 8/1111:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Thu 8/138:50 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 7/15![Southwest logo]()
$351
This Southwest deal was found by Cheapflights users on 7/15. 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 8/1311:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Thu 8/2010:15 am
MDW
- PDX
2 stops10h 45m
Southwest
Deal found 7/15![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 7/14. 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 8/1412:40 pm
PDX
- MDW
2 stops9h 05m
Southwest
Mon 8/179:00 am
MDW
- PDX
1 stop8h 00m
Southwest
Deal found 7/14![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 7/16. 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
Fri 8/216:15 pm
MDW
- PDX
1 stop7h 00m
Southwest
Deal found 7/16![Southwest logo]()
$342
This Southwest deal was found by Cheapflights users on 7/15. 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 8/1712:40 pm
PDX
- MDW
2 stops9h 05m
Southwest
Fri 8/216:15 am
MDW
- PDX
2 stops10h 30m
Southwest
Deal found 7/15![Southwest logo]()
$343
This Southwest deal was found by Cheapflights users on 7/15. 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 8/2112:40 pm
PDX
- MDW
2 stops9h 05m
Southwest
Tue 8/256:00 am
MDW
- PDX
1 stop7h 20m
Southwest
Deal found 7/15![Southwest logo]()
$328
This Southwest deal was found by Cheapflights users on 7/14. 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 8/2112:40 pm
PDX
- MDW
2 stops9h 05m
Southwest
Sun 8/307:55 am
MDW
- PDX
1 stop8h 10m
Southwest
Deal found 7/14![Southwest logo]()
$338
This Delta deal was found by Cheapflights users on 7/16. 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
Wed 9/92:00 pm
MDW
- PDX
1 stop8h 16m
Delta
Deal found 7/16![Delta logo]()
$327
This Delta deal was found by Cheapflights users on 7/16. 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.
Sun 8/3011:20 pm
PDX
- MDW
1 stop7h 57m
Delta
Fri 9/1111:35 am
MDW
- PDX
1 stop9h 24m
Delta
Deal found 7/16![Delta logo]()
$337
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 18, 2026.
Search for one-way flight options from Portland to Midway. Find affordable one-way fares based on user searches. Data last updated July 18, 2026.
This Delta deal was found by Cheapflights users on 7/15. 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 9/1212:25 am
PDX
- MDW
1 stop6h 23m
Delta
Deal found 7/15![Delta logo]()
$169
This Southwest deal was found by Cheapflights users on 7/16. 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 8/205:45 am
PDX
- MDW
2 stops9h 35m
Southwest
Deal found 7/16![Southwest logo]()
$174
This Southwest deal was found by Cheapflights users on 7/13. 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 8/611:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 7/13![Southwest logo]()
$179
This Southwest deal was found by Cheapflights users on 7/13. 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 9/1111:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 7/13![Southwest logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 7/17. 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.
Wed 8/195:56 pm
PDX
- MDW
2 stops26h 51m
Frontier
Deal found 7/17![Frontier logo]()
$183
This Southwest deal was found by Cheapflights users on 7/14. 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 8/318:00 am
PDX
- MDW
1 stop7h 00m
Southwest
Deal found 7/14![Southwest logo]()
$184
This Southwest deal was found by Cheapflights users on 7/13. 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 8/115:50 am
PDX
- MDW
2 stops8h 45m
Southwest
Deal found 7/13![Southwest logo]()
$189
This Delta deal was found by Cheapflights users on 7/13. 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 1/139:45 pm
PDX
- MDW
1 stop10h 07m
Delta
Deal found 7/13![Delta logo]()
$190
This Southwest deal was found by Cheapflights users on 7/17. 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 7/17![Southwest logo]()
$193
This Southwest deal was found by Cheapflights users on 7/16. 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 8/1211:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 7/16![Southwest logo]()
$194
This Southwest deal was found by Cheapflights users on 7/13. 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 9/1811:35 am
PDX
- MDW
Nonstop4h 00m
Southwest
Deal found 7/13![Southwest logo]()
$195
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 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $327 (Delta) |
One-way from | $169 (Delta) |
Popular in | August |
Cheapest in | January |
Average price | $375 |
Good round-trip deal | $377 or less |
Good one-way deal | $228 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 18, 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
PortlandChicago
PDX - MDW
PDXMDW
Portland
Sat 8/29
9:00 am-8:45 pm
2 stops9h 45m
Chicago Midway
Sat 9/5
10:15 am-6:25 pm
2 stops10h 10m
$327
PortlandChicago
PDX - MDW
PDXMDW
Portland
Wed 8/26
5:50 am-4:35 pm
2 stops8h 45m
Chicago Midway
Fri 8/28
10:25 am-7:00 pm
2 stops10h 35m
$333
PortlandChicago
PDX - MDW
PDXMDW
Portland
Mon 10/12
9:15 pm-5:45 am
1 stop6h 30m
Chicago Midway
Thu 10/15
5:15 am-12:35 pm
2 stops9h 20m
$338
PortlandChicago
PDX - MDW
PDXMDW
Portland
Thu 12/3
6:15 am-4:50 pm
1 stop8h 35m
Chicago Midway
Mon 12/14
1:05 pm-10:26 pm
1 stop11h 21m
$377
PortlandChicago
PDX - MDW
PDXMDW
Portland
Tue 11/3
6:00 am-4:39 pm
1 stop8h 39m
Chicago Midway
Sat 11/7
6:00 am-1:10 pm
1 stop9h 10m
$377
PortlandChicago
PDX - MDW
PDXMDW
Portland
Wed 11/11
11:15 am-5:00 pm
Nonstop3h 45m
Chicago Midway
Sun 11/15
6:05 pm-12:10 am
1 stop8h 05m
$383
Quickest round-trip
PortlandChicago
PDX - MDW
PDXMDW
Portland
Fri 9/18
6:15 am-12:10 pm
Nonstop3h 55m
Chicago Midway
Sun 9/20
9:20 pm-11:30 pm
Nonstop4h 10m
$389
PortlandChicago
PDX - MDW
PDXMDW
Portland
Thu 12/3
10:55 pm-8:45 am
1 stop7h 50m
Chicago Midway
Tue 12/8
12:30 pm-7:43 pm
1 stop9h 13m
$392
PortlandChicago
PDX - MDW
PDXMDW
Portland
Thu 8/6
12:40 pm-11:45 pm
2 stops9h 05m
Chicago Midway
Mon 8/10
6:15 am-2:45 pm
2 stops10h 30m
$428
Cheapest one-way
PortlandChicago
PDX - MDW
PDXMDW
Portland
Sat 9/12
12:25 am-8:48 am
1 stop6h 23m
$169
Showing 1-10 of 19 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.
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Everything you need to know about your flight from Portland to Chicago Midway Airport
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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 18, 2026.
It’s typically best to fly out from Portland to Chicago Midway Airport at noon. Doing so could potentially save you 22% on the flight price compared to flying in the evening, 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 18, 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.
Crew
8.6
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Crew
8.6
Boarding
8.1
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
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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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 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$231 | Average$360 | FlexibilityNo cancel fee | On-time63% |