$155+ 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 8/10. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MDW
Jul 10 — Jul 171
Round-trip
1 adult, Economy
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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 June 10, 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 June 10, 2026.
This Southwest deal was found by Cheapflights users on 6/7. 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 8/76:20 am
PDX
- MDW
2 stops8h 40m
Southwest
Mon 8/108:50 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 6/7![Southwest logo]()
$317
This Delta deal was found by Cheapflights users on 6/9. 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 9/711:20 pm
PDX
- MDW
1 stop7h 22m
Delta
Mon 9/1410:48 am
MDW
- PDX
1 stop10h 11m
Delta
Deal found 6/9![Delta logo]()
$318
This Southwest deal was found by Cheapflights users on 6/10. 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 9/97:50 am
PDX
- MDW
2 stops10h 00m
Southwest
Mon 9/146:15 am
MDW
- PDX
2 stops10h 30m
Southwest
Deal found 6/10![Southwest logo]()
$319
This Southwest deal was found by Cheapflights users on 6/6. 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 7/711:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Tue 7/149:10 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 6/6![Southwest logo]()
$320
This Delta deal was found by Cheapflights users on 6/10. 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 8/512:35 am
PDX
- MDW
1 stop6h 04m
Delta
Mon 8/107:25 pm
MDW
- PDX
1 stop5h 55m
Delta
Deal found 6/10![Delta logo]()
$321
This Southwest deal was found by Cheapflights users on 6/10. 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 10/911:35 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Mon 10/129:50 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 6/10![Southwest logo]()
$322
This Southwest deal was found by Cheapflights users on 6/8. 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 10/34:45 pm
PDX
- MDW
2 stops11h 15m
Southwest
Mon 10/56:15 pm
MDW
- PDX
2 stops8h 30m
Southwest
Deal found 6/8![Southwest logo]()
$323
This Southwest deal was found by Cheapflights users on 6/9. 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 8/38:15 pm
PDX
- MDW
1 stop7h 30m
Southwest
Thu 8/68:50 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 6/9![Southwest logo]()
$324
This Southwest deal was found by Cheapflights users on 6/9. 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 7/2211:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Wed 7/295:05 am
MDW
- PDX
1 stop6h 55m
Southwest
Deal found 6/9![Southwest logo]()
$325
This Southwest deal was found by Cheapflights users on 6/8. 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 7/2111:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Sun 7/269:50 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 6/8![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 6/10. 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 8/146:20 am
PDX
- MDW
2 stops8h 40m
Southwest
Mon 8/176:40 am
MDW
- PDX
1 stop7h 00m
Southwest
Deal found 6/10![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 6/10. 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 8/1810:45 pm
PDX
- MDW
1 stop10h 50m
Southwest
Mon 8/245:00 pm
MDW
- PDX
2 stops7h 45m
Southwest
Deal found 6/10![Southwest logo]()
$328
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 June 10, 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 June 10, 2026.
This Southwest deal was found by Cheapflights users on 6/9. 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 8/38:15 pm
PDX
- MDW
1 stop7h 30m
Southwest
Thu 8/68:50 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 6/9![Southwest logo]()
$324
This Delta deal was found by Cheapflights users on 6/7. 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 8/1312:35 am
PDX
- MDW
1 stop6h 04m
Delta
Mon 8/171:51 pm
MDW
- PDX
1 stop8h 26m
Delta
Deal found 6/7![Delta logo]()
$357
This Southwest deal was found by Cheapflights users on 6/6. 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 9/308:00 am
PDX
- MDW
1 stop7h 05m
Southwest
Wed 9/308:55 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 6/6![Southwest logo]()
$325
This Southwest deal was found by Cheapflights users on 6/7. 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 9/3010:45 pm
PDX
- MDW
1 stop8h 10m
Southwest
Sat 10/37:20 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 6/7![Southwest logo]()
$325
This Southwest deal was found by Cheapflights users on 6/10. 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 8/2112:20 pm
PDX
- MDW
2 stops9h 00m
Southwest
Mon 8/244:55 pm
MDW
- PDX
1 stop8h 20m
Southwest
Deal found 6/10![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 6/10. 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 7/3011:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Mon 8/39:35 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 6/10![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 6/10. 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 8/151:35 pm
PDX
- MDW
2 stops12h 55m
Southwest
Tue 8/1810:10 am
MDW
- PDX
2 stops10h 05m
Southwest
Deal found 6/10![Southwest logo]()
$339
This Southwest deal was found by Cheapflights users on 6/6. 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 7/259:20 pm
PDX
- MDW
1 stop7h 50m
Southwest
Mon 7/275:15 am
MDW
- PDX
1 stop6h 10m
Southwest
Deal found 6/6![Southwest logo]()
$366
This Southwest deal was found by Cheapflights users on 6/8. 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 7/311:05 pm
PDX
- MDW
2 stops9h 35m
Southwest
Mon 8/39:35 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 6/8![Southwest logo]()
$372
This Southwest deal was found by Cheapflights users on 6/9. 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 10/17:30 am
PDX
- MDW
2 stops8h 20m
Southwest
Sun 10/45:30 am
MDW
- PDX
1 stop8h 05m
Southwest
Deal found 6/9![Southwest logo]()
$382
This Southwest deal was found by Cheapflights users on 6/5. 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 7/1311:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Thu 7/169:35 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 6/5![Southwest logo]()
$382
This Southwest deal was found by Cheapflights users on 6/10. 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 7/91:05 pm
PDX
- MDW
2 stops9h 35m
Southwest
Sun 7/129:50 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 6/10![Southwest logo]()
$392
Last-minute flights from Portland to MidwayDiscover last-minute flight deals from Portland to Midway. Data last updated June 10, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Midway. Data last updated June 10, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/6. 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 7/711:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Tue 7/149:10 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 6/6![Southwest logo]()
$320
This Southwest deal was found by Cheapflights users on 6/10. 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 7/811:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Wed 7/159:10 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 6/10![Southwest logo]()
$331
This Southwest deal was found by Cheapflights users on 6/8. 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 7/96:00 am
PDX
- MDW
Nonstop3h 50m
Southwest
Sun 7/129:50 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 6/8![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 6/9. 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 7/155:55 pm
PDX
- MDW
1 stop9h 30m
Southwest
Wed 7/225:35 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 6/9![Southwest logo]()
$330
This Southwest deal was found by Cheapflights users on 6/10. 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 7/1711:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Fri 8/78:50 pm
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 6/10![Southwest logo]()
$322
This Southwest deal was found by Cheapflights users on 6/8. 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 7/2111:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Sun 7/269:50 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 6/8![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 6/9. 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 7/2211:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Wed 7/295:05 am
MDW
- PDX
1 stop6h 55m
Southwest
Deal found 6/9![Southwest logo]()
$325
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 June 10, 2026.
Search for one-way flight options from Portland to Midway. Find affordable one-way fares based on user searches. Data last updated June 10, 2026.
This Southwest deal was found by Cheapflights users on 6/9. 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 8/107:00 pm
PDX
- MDW
1 stop8h 40m
Southwest
Deal found 6/9![Southwest logo]()
$155
This Southwest deal was found by Cheapflights users on 6/8. 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 7/1511:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Deal found 6/8![Southwest logo]()
$158
This Southwest deal was found by Cheapflights users on 6/10. 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 8/206:20 am
PDX
- MDW
2 stops8h 40m
Southwest
Deal found 6/10![Southwest logo]()
$161
This Southwest deal was found by Cheapflights users on 6/9. 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 7/2911:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Deal found 6/9![Southwest logo]()
$163
This Delta deal was found by Cheapflights users on 6/8. 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 7/1012:33 am
PDX
- MDW
1 stop6h 04m
Delta
Deal found 6/8![Delta logo]()
$168
This Southwest deal was found by Cheapflights users on 6/7. 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 7/2411:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Deal found 6/7![Southwest logo]()
$169
This Southwest deal was found by Cheapflights users on 6/7. 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 12/46:05 am
PDX
- MDW
Nonstop3h 45m
Southwest
Deal found 6/7![Southwest logo]()
$172
This Southwest deal was found by Cheapflights users on 6/8. 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 8/57:05 am
PDX
- MDW
2 stops8h 05m
Southwest
Deal found 6/8![Southwest logo]()
$173
This Southwest deal was found by Cheapflights users on 6/7. 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 7/111:30 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Deal found 6/7![Southwest logo]()
$174
This Southwest deal was found by Cheapflights users on 6/9. 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 8/47:50 am
PDX
- MDW
2 stops10h 00m
Southwest
Deal found 6/9![Southwest logo]()
$178
This Delta deal was found by Cheapflights users on 6/7. 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 7/2411:15 pm
PDX
- MDW
1 stop7h 58m
Delta
Deal found 6/7![Delta logo]()
$179
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 June 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $317 (Southwest) |
One-way from | $155 (Southwest) |
Popular in | May |
Cheapest in | January |
Average price | $331 |
Good round-trip deal | $423 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 June 10, 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
Mon 8/3
8:15 pm-5:45 am
1 stop7h 30m
Chicago Midway
Thu 8/6
8:50 pm-11:05 pm
Nonstop4h 15m
$324
PortlandChicago
PDX - MDW
PDXMDW
Portland
Wed 9/30
8:00 am-5:05 pm
1 stop7h 05m
Chicago Midway
Wed 9/30
8:55 pm-11:10 pm
Nonstop4h 15m
$325
PortlandChicago
PDX - MDW
PDXMDW
Portland
Wed 9/30
10:45 pm-8:55 am
1 stop8h 10m
Chicago Midway
Sat 10/3
7:20 pm-9:35 pm
Nonstop4h 15m
$325
PortlandChicago
PDX - MDW
PDXMDW
Portland
Fri 8/21
12:20 pm-11:20 pm
2 stops9h 00m
Chicago Midway
Mon 8/24
4:55 pm-11:15 pm
1 stop8h 20m
$327
Quickest round-trip
PortlandChicago
PDX - MDW
PDXMDW
Portland
Thu 7/30
11:30 pm-5:20 am
Nonstop3h 50m
Chicago Midway
Mon 8/3
9:35 pm-11:55 pm
Nonstop4h 20m
$337
PortlandChicago
PDX - MDW
PDXMDW
Portland
Sat 8/15
1:35 pm-4:30 am
2 stops12h 55m
Chicago Midway
Tue 8/18
10:10 am-6:15 pm
2 stops10h 05m
$339
PortlandChicago
PDX - MDW
PDXMDW
Portland
Thu 8/13
12:35 am-8:39 am
1 stop6h 04m
Chicago Midway
Mon 8/17
1:51 pm-8:17 pm
1 stop8h 26m
$357
PortlandChicago
PDX - MDW
PDXMDW
Portland
Sat 7/25
9:20 pm-7:10 am
1 stop7h 50m
Chicago Midway
Mon 7/27
5:15 am-9:25 am
1 stop6h 10m
$366
PortlandChicago
PDX - MDW
PDXMDW
Portland
Fri 7/31
1:05 pm-12:40 am
2 stops9h 35m
Chicago Midway
Mon 8/3
9:35 pm-11:55 pm
Nonstop4h 20m
$372
PortlandChicago
PDX - MDW
PDXMDW
Portland
Thu 10/1
7:30 am-5:50 pm
2 stops8h 20m
Chicago Midway
Sun 10/4
5:30 am-11:35 am
1 stop8h 05m
$382
Showing 1-10 of 24 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 June.
| 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 May is currently the most expensive (average of $382). 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 June 10, 2026.
It’s typically best to fly out from Portland to Chicago Midway Airport at noon. Doing so could potentially save you 27% 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
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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 June 10, 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
Comfort
8.0
Overall
7.9
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Comfort
8.0
Overall
7.9
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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
Hammond
Porter
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Other flights to Midway
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Portland and Midway flights
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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 June 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$217 | Average$357 | FlexibilityNo cancel fee | On-time63% |