$161+ 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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MDW
Sep 17 — Sep 241
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
Cheapest
Best
Last-minute
One-way
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 August 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 August 18, 2026.
This Southwest deal was found by Cheapflights users on 8/13. 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.
Sat 9/125:30 pm -
1 stop9h 30m
Wed 9/168:55 pm -
Nonstop4h 20m
Deal found 8/13![Southwest logo]()
$311
This Delta deal was found by Cheapflights users on 8/13. 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 10/296:50 am -
1 stop7h 29m
Tue 11/35:31 pm -
1 stop8h 13m
Deal found 8/13![Delta logo]()
$313
This Delta deal was found by Cheapflights users on 8/13. 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.
Fri 9/411:20 pm -
1 stop7h 57m
Wed 9/92:00 pm -
1 stop8h 16m
Deal found 8/13![Delta logo]()
$315
This Delta deal was found by Cheapflights users on 8/13. 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.
Fri 9/411:20 pm -
1 stop7h 57m
Thu 9/1011:35 am -
1 stop9h 24m
Deal found 8/13![Delta logo]()
$316
This Southwest deal was found by Cheapflights users on 8/13. 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 11/36:00 am -
Nonstop3h 50m
Sat 11/710:25 am -
Nonstop4h 35m
Deal found 8/13![Southwest logo]()
$317
This Southwest deal was found by Cheapflights users on 8/13. 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 9/311:30 pm -
Nonstop3h 55m
Wed 9/238:55 pm -
Nonstop4h 20m
Deal found 8/13![Southwest logo]()
$320
This Southwest deal was found by Cheapflights users on 8/14. 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 9/1112:40 pm -
2 stops9h 10m
Mon 9/148:50 pm -
Nonstop4h 20m
Deal found 8/14![Southwest logo]()
$321
This Southwest deal was found by Cheapflights users on 8/13. 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.
Sat 9/121:35 pm -
2 stops12h 55m
Thu 9/178:50 pm -
Nonstop4h 20m
Deal found 8/13![Southwest logo]()
$322
This Southwest deal was found by Cheapflights users on 8/13. 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 9/411:30 pm -
Nonstop3h 55m
Sun 9/68:35 pm -
Nonstop4h 15m
Deal found 8/13![Southwest logo]()
$324
This Southwest deal was found by Cheapflights users on 8/13. 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.
Mon 9/1411:30 pm -
Nonstop3h 55m
Tue 9/2212:00 pm -
2 stops9h 55m
Deal found 8/13![Southwest logo]()
$325
This Southwest deal was found by Cheapflights users on 8/13. 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 9/107:00 pm -
1 stop8h 40m
Thu 9/178:50 pm -
Nonstop4h 20m
Deal found 8/13![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 8/13. 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 9/14:10 pm -
1 stop10h 50m
Sun 9/68:25 am -
1 stop7h 50m
Deal found 8/13![Southwest logo]()
$327
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 August 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 August 18, 2026.
This Delta deal was found by Cheapflights users on 8/13. 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 10/296:50 am -
1 stop7h 29m
Tue 11/35:31 pm -
1 stop8h 13m
Deal found 8/13![Delta logo]()
$313
This Southwest deal was found by Cheapflights users on 8/13. 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.
Wed 10/212:15 pm -
1 stop7h 35m
Sun 10/2510:30 pm -
Nonstop4h 25m
Deal found 8/13![Southwest logo]()
$342
This Delta deal was found by Cheapflights users on 8/13. 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.
Fri 9/411:20 pm -
1 stop7h 57m
Wed 9/92:00 pm -
1 stop8h 16m
Deal found 8/13![Delta logo]()
$315
This Southwest deal was found by Cheapflights users on 8/13. 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.
Wed 9/93:00 pm -
1 stop11h 30m
Sat 9/122:15 pm -
2 stops9h 10m
Deal found 8/13![Southwest logo]()
$348
This Southwest deal was found by Cheapflights users on 8/17. 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.
Sat 10/2411:35 pm -
Nonstop3h 50m
Sun 11/19:15 pm -
Nonstop4h 40m
Deal found 8/17![Southwest logo]()
$357
This Delta deal was found by Cheapflights users on 8/14. 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 11/1012:45 am -
1 stop6h 05m
Mon 11/165:25 pm -
1 stop8h 34m
Deal found 8/14![Delta logo]()
$377
This Southwest deal was found by Cheapflights users on 8/17. 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.
Thu 11/57:00 pm -
1 stop8h 45m
Sun 11/89:15 pm -
Nonstop4h 40m
Deal found 8/17![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 8/17. 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.
Thu 10/229:30 pm -
1 stop6h 25m
Sun 10/2510:30 pm -
Nonstop4h 25m
Deal found 8/17![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 8/15. 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 9/147:55 pm -
1 stop7h 50m
Mon 9/216:30 pm -
Nonstop4h 15m
Deal found 8/15![Southwest logo]()
$367
This Southwest deal was found by Cheapflights users on 8/16. 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 9/116:15 am -
Nonstop3h 55m
Tue 9/158:55 pm -
Nonstop4h 20m
Deal found 8/16![Southwest logo]()
$373
Last-minute flights from Portland to MidwayDiscover last-minute flight deals from Portland to Midway. Data last updated August 18, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Midway. Data last updated August 18, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/13. 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 9/14:10 pm -
1 stop10h 50m
Sun 9/68:25 am -
1 stop7h 50m
Deal found 8/13![Southwest logo]()
$327
This Southwest deal was found by Cheapflights users on 8/13. 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.
Wed 9/27:05 am -
2 stops8h 05m
Sat 9/56:00 pm -
Nonstop4h 20m
Deal found 8/13![Southwest logo]()
$331
This Southwest deal was found by Cheapflights users on 8/13. 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 9/311:30 pm -
Nonstop3h 55m
Wed 9/238:55 pm -
Nonstop4h 20m
Deal found 8/13![Southwest logo]()
$320
This Delta deal was found by Cheapflights users on 8/13. 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.
Fri 9/411:20 pm -
1 stop7h 57m
Wed 9/92:00 pm -
1 stop8h 16m
Deal found 8/13![Delta logo]()
$315
This Delta deal was found by Cheapflights users on 8/13. 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.
Fri 9/411:20 pm -
1 stop7h 57m
Thu 9/1011:35 am -
1 stop9h 24m
Deal found 8/13![Delta logo]()
$316
This Southwest deal was found by Cheapflights users on 8/13. 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 9/411:30 pm -
Nonstop3h 55m
Sun 9/68:35 pm -
Nonstop4h 15m
Deal found 8/13![Southwest logo]()
$324
This Southwest deal was found by Cheapflights users on 8/13. 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 9/107:00 pm -
1 stop8h 40m
Thu 9/178:50 pm -
Nonstop4h 20m
Deal found 8/13![Southwest logo]()
$326
This Southwest deal was found by Cheapflights users on 8/14. 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 9/1112:40 pm -
2 stops9h 10m
Mon 9/148:50 pm -
Nonstop4h 20m
Deal found 8/14![Southwest logo]()
$321
This Southwest deal was found by Cheapflights users on 8/13. 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.
Sat 9/125:30 pm -
1 stop9h 30m
Wed 9/168:55 pm -
Nonstop4h 20m
Deal found 8/13![Southwest logo]()
$311
This Southwest deal was found by Cheapflights users on 8/13. 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.
Sat 9/121:35 pm -
2 stops12h 55m
Thu 9/178:50 pm -
Nonstop4h 20m
Deal found 8/13![Southwest logo]()
$322
This Southwest deal was found by Cheapflights users on 8/13. 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.
Mon 9/1411:30 pm -
Nonstop3h 55m
Tue 9/2212:00 pm -
2 stops9h 55m
Deal found 8/13![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 August 18, 2026.
Search for one-way flight options from Portland to Midway. Find affordable one-way fares based on user searches. Data last updated August 18, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1912:25 pm -
2 stops45h 52m
Deal found 8/16![Frontier logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1311:49 am -
2 stops22h 28m
Deal found 8/15![Frontier logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/1311:02 am -
2 stops22h 57m
Deal found 8/14![Frontier logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/133:47 pm -
2 stops18h 20m
Deal found 8/16![Frontier logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Fri 9/1112:38 pm -
2 stops21h 21m
Deal found 8/17![Frontier logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1511:06 am -
2 stops34h 37m
Deal found 8/13![Frontier logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2411:02 am -
2 stops34h 42m
Deal found 8/13![Frontier logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1611:06 am -
2 stops34h 37m
Deal found 8/13![Frontier logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/163:47 pm -
2 stops28h 06m
Deal found 8/15![Frontier logo]()
$177
This Southwest deal was found by Cheapflights users on 8/16. 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 -
Nonstop3h 55m
Deal found 8/16![Southwest 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 August 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $311 (Southwest) |
One-way from | $161 (Kiwi.com) |
Popular in | August |
Cheapest in | January |
Average price | $402 |
Good round-trip deal | $364 or less |
Good one-way deal | $223 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 August 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 Portland - MDW Chicago Midway
PDXMDW
Portland
Thu 10/29
6:50 am-4:19 pm
1 stop7h 29m
Chicago Midway
Tue 11/3
5:31 pm-11:44 pm
1 stop8h 13m
$313
PortlandChicago
PDX Portland - MDW Chicago Midway
PDXMDW
Portland
Fri 9/4
11:20 pm-9:17 am
1 stop7h 57m
Chicago Midway
Wed 9/9
2:00 pm-8:16 pm
1 stop8h 16m
$315
PortlandChicago
PDX Portland - MDW Chicago Midway
PDXMDW
Portland
Wed 10/21
2:15 pm-11:50 pm
1 stop7h 35m
Chicago Midway
Sun 10/25
10:30 pm-12:55 am
Nonstop4h 25m
$342
PortlandChicago
PDX Portland - MDW Chicago Midway
PDXMDW
Portland
Wed 9/9
3:00 pm-4:30 am
1 stop11h 30m
Chicago Midway
Sat 9/12
2:15 pm-9:25 pm
2 stops9h 10m
$348
PortlandChicago
PDX Portland - MDW Chicago Midway
PDXMDW
Portland
Sat 10/24
11:35 pm-5:25 am
Nonstop3h 50m
Chicago Midway
Sun 11/1
9:15 pm-11:55 pm
Nonstop4h 40m
$357
PortlandChicago
PDX Portland - MDW Chicago Midway
PDXMDW
Portland
Thu 11/5
7:00 pm-5:45 am
1 stop8h 45m
Chicago Midway
Sun 11/8
9:15 pm-11:55 pm
Nonstop4h 40m
$367
PortlandChicago
PDX Portland - MDW Chicago Midway
PDXMDW
Portland
Thu 10/22
9:30 pm-5:55 am
1 stop6h 25m
Chicago Midway
Sun 10/25
10:30 pm-12:55 am
Nonstop4h 25m
$367
PortlandChicago
PDX Portland - MDW Chicago Midway
PDXMDW
Portland
Mon 9/14
7:55 pm-5:45 am
1 stop7h 50m
Chicago Midway
Mon 9/21
6:30 pm-8:45 pm
Nonstop4h 15m
$367
Quickest round-trip
PortlandChicago
PDX Portland - MDW Chicago Midway
PDXMDW
Portland
Fri 9/11
6:15 am-12:10 pm
Nonstop3h 55m
Chicago Midway
Tue 9/15
8:55 pm-11:15 pm
Nonstop4h 20m
$373
PortlandChicago
PDX Portland - MDW Chicago Midway
PDXMDW
Portland
Tue 11/10
12:45 am-8:50 am
1 stop6h 05m
Chicago Midway
Mon 11/16
5:25 pm-11:59 pm
1 stop8h 34m
$377
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 August.
| 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 August is currently the most expensive (average of $402). 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 August 18, 2026.
It’s typically best to fly out from Portland to Chicago Midway Airport at noon. Doing so could potentially save you 11% 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 August 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.
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Boarding
8.1
Food
7.0
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
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Top airline flying from Portland to Midway
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$266 | Average$365 | FlexibilityNo cancel fee | On-time63% |