$102+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MDW
Mar 23 — Mar 301
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 February 21, 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 February 21, 2026.
This Southwest deal was found by Cheapflights users on 2/18. 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.
Wed 5/611:55 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Sat 5/96:05 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 2/18![Southwest logo]()
$231
This Southwest deal was found by Cheapflights users on 2/18. 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.
Tue 3/316:15 am
PDX
- MDW
1 stop8h 55m
Southwest
Tue 4/78:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 2/18![Southwest logo]()
$248
This Southwest deal was found by Cheapflights users on 2/18. 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 4/2011:55 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Tue 4/218:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 2/18![Southwest logo]()
$249
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/3012:30 am
PDX
- MDW
1 stop6h 20m
Delta
Tue 4/72:05 pm
MDW
- PDX
1 stop8h 20m
Delta
Deal found 2/19![Delta logo]()
$251
This Southwest deal was found by Cheapflights users on 2/18. 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.
Tue 9/1511:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Tue 9/2210:20 am
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 2/18![Southwest logo]()
$255
This Southwest deal was found by Cheapflights users on 2/18. 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 6/111:55 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Wed 6/38:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 2/18![Southwest logo]()
$256
This Southwest deal was found by Cheapflights users on 2/16. 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 4/85:40 am
PDX
- MDW
Nonstop3h 55m
Southwest
Wed 4/85:35 pm
MDW
- PDX
1 stop7h 25m
Southwest
Deal found 2/16![Southwest logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 2/17. 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.
Sat 3/711:47 am
PDX
- MDW
1 stop8h 54m
Frontier
Wed 3/1111:25 am
MDW
- PDX
2 stops25h 44m
Frontier
Deal found 2/17![Frontier logo]()
$264
This Southwest deal was found by Cheapflights users on 2/17. 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 8/811:30 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Sat 8/1510:15 am
MDW
- PDX
Nonstop4h 15m
Southwest
Deal found 2/17![Southwest logo]()
$265
This Southwest deal was found by Cheapflights users on 2/19. 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.
Sat 5/237:05 pm
PDX
- MDW
1 stop8h 35m
Southwest
Mon 5/259:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 2/19![Southwest logo]()
$266
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 February 21, 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 February 21, 2026.
This Southwest deal was found by Cheapflights users on 2/16. 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 4/111:55 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Wed 4/88:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 2/16![Southwest logo]()
$231
This Delta deal was found by Cheapflights users on 2/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2112:30 am
PDX
- MDW
1 stop6h 16m
Delta
Sat 4/252:12 pm
MDW
- PDX
1 stop7h 55m
Delta
Deal found 2/18![Delta logo]()
$251
This Southwest deal was found by Cheapflights users on 2/16. 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 4/187:05 pm
PDX
- MDW
1 stop8h 35m
Southwest
Tue 4/218:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 2/16![Southwest logo]()
$241
This Delta deal was found by Cheapflights users on 2/17. 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.
Mon 4/1312:30 am
PDX
- MDW
1 stop6h 16m
Delta
Sat 4/182:12 pm
MDW
- PDX
1 stop7h 55m
Delta
Deal found 2/17![Delta logo]()
$251
This Southwest deal was found by Cheapflights users on 2/17. 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.
Wed 4/85:40 am
PDX
- MDW
Nonstop3h 55m
Southwest
Thu 4/99:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 2/17![Southwest logo]()
$249
This Delta deal was found by Cheapflights users on 2/16. 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.
Tue 3/3111:15 pm
PDX
- MDW
1 stop7h 38m
Delta
Wed 4/82:05 pm
MDW
- PDX
1 stop8h 20m
Delta
Deal found 2/16![Delta logo]()
$251
This Southwest deal was found by Cheapflights users on 2/18. 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.
Tue 5/511:55 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Fri 5/89:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 2/18![Southwest logo]()
$249
This Southwest deal was found by Cheapflights users on 2/16. 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 4/85:40 am
PDX
- MDW
Nonstop3h 55m
Southwest
Wed 4/85:35 pm
MDW
- PDX
1 stop7h 25m
Southwest
Deal found 2/16![Southwest logo]()
$258
This Southwest deal was found by Cheapflights users on 2/18. 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.
Tue 5/511:55 pm
PDX
- MDW
Nonstop3h 55m
Southwest
Thu 5/75:25 am
MDW
- PDX
1 stop7h 30m
Southwest
Deal found 2/18![Southwest logo]()
$259
This Southwest deal was found by Cheapflights users on 2/17. 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.
Tue 3/177:00 pm
PDX
- MDW
1 stop8h 45m
Southwest
Thu 3/1910:20 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 2/17![Southwest logo]()
$259
Last-minute flights from Portland to MidwayDiscover last-minute flight deals from Portland to Midway. Data last updated February 21, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Midway. Data last updated February 21, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 2/17. 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.
Sat 3/711:47 am
PDX
- MDW
1 stop8h 54m
Frontier
Wed 3/1111:25 am
MDW
- PDX
2 stops25h 44m
Frontier
Deal found 2/17![Frontier logo]()
$264
This Southwest deal was found by Cheapflights users on 2/18. 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.
Tue 3/105:25 am
PDX
- MDW
Nonstop3h 55m
Southwest
Sat 3/1410:30 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 2/18![Southwest logo]()
$249
This Southwest deal was found by Cheapflights users on 2/18. 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.
Thu 3/125:20 am
PDX
- MDW
Nonstop3h 55m
Southwest
Wed 3/188:45 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 2/18![Southwest logo]()
$269
This Southwest deal was found by Cheapflights users on 2/17. 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.
Tue 3/1711:55 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Thu 3/1910:20 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 2/17![Southwest logo]()
$267
This Southwest deal was found by Cheapflights users on 2/18. 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.
Tue 3/177:00 pm
PDX
- MDW
1 stop8h 45m
Southwest
Mon 3/2310:20 pm
MDW
- PDX
Nonstop4h 25m
Southwest
Deal found 2/18![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/3012:30 am
PDX
- MDW
1 stop6h 20m
Delta
Tue 4/72:05 pm
MDW
- PDX
1 stop8h 20m
Delta
Deal found 2/19![Delta logo]()
$251
This Southwest deal was found by Cheapflights users on 2/18. 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.
Tue 3/315:25 am
PDX
- MDW
Nonstop3h 55m
Southwest
Tue 4/78:50 pm
MDW
- PDX
Nonstop4h 20m
Southwest
Deal found 2/18![Southwest logo]()
$231
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 February 21, 2026.
Search for one-way flight options from Portland to Midway. Find affordable one-way fares based on user searches. Data last updated February 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Wed 4/151:48 pm
PDX
- MDW
2 stops30h 34m
Frontier
Deal found 2/20![Frontier logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 2/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2212:38 pm
PDX
- MDW
2 stops24h 26m
Frontier
Deal found 2/18![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 2/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2512:27 pm
PDX
- MDW
2 stops46h 08m
Frontier
Deal found 2/18![Frontier logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 2/20. 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.
Thu 4/1611:48 am
PDX
- MDW
2 stops31h 49m
Frontier
Deal found 2/20![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 2/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/141:48 pm
PDX
- MDW
2 stops27h 43m
Frontier
Deal found 2/18![Frontier logo]()
$115
This Southwest deal was found by Cheapflights users on 2/20. 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.
Wed 3/2511:55 pm
PDX
- MDW
Nonstop3h 50m
Southwest
Deal found 2/20![Southwest logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 2/17. 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.
Thu 4/2311:48 am
PDX
- MDW
2 stops32h 33m
Frontier
Deal found 2/17![Frontier logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 2/17. 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.
Sat 5/1612:27 pm
PDX
- MDW
2 stops31h 52m
Frontier
Deal found 2/17![Frontier logo]()
$121
This Southwest deal was found by Cheapflights users on 2/20. 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 3/285:20 am
PDX
- MDW
Nonstop3h 55m
Southwest
Deal found 2/20![Southwest logo]()
$123
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/1412:47 pm
PDX
- MDW
1 stop7h 58m
Frontier
Deal found 2/19![Frontier logo]()
$125
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/1612:30 am
PDX
- MDW
1 stop6h 20m
Delta
Deal found 2/20![Delta logo]()
$126
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 February 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $231 (Southwest) |
One-way from | $102 (Kiwi.com) |
Popular in | July |
Cheapest in | January |
Average price | $475 |
Good round-trip deal | $338 or less |
Good one-way deal | $168 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 February 21, 2026.
Use the filters below to find and compare flights from Portland to Chicago Midway Airport that are best for you.
Fly from
Portland
Fly to
Midway
Route
Depart
Return
Price
PortlandChicago
PDX - MDW
PDXMDW
Portland
Wed 4/1
11:55 pm-5:45 am
Nonstop3h 50m
Chicago Midway
Wed 4/8
8:50 pm-11:10 pm
Nonstop4h 20m
$231
PortlandChicago
PDX - MDW
PDXMDW
Portland
Sat 4/18
7:05 pm-5:40 am
1 stop8h 35m
Chicago Midway
Tue 4/21
8:50 pm-11:10 pm
Nonstop4h 20m
$241
PortlandChicago
PDX - MDW
PDXMDW
Portland
Wed 4/8
5:40 am-11:35 am
Nonstop3h 55m
Chicago Midway
Thu 4/9
9:50 pm-12:10 am
Nonstop4h 20m
$249
PortlandChicago
PDX - MDW
PDXMDW
Portland
Tue 5/5
11:55 pm-5:50 am
Nonstop3h 55m
Chicago Midway
Fri 5/8
9:50 pm-12:10 am
Nonstop4h 20m
$249
PortlandChicago
PDX - MDW
PDXMDW
Portland
Tue 4/21
12:30 am-8:46 am
1 stop6h 16m
Chicago Midway
Sat 4/25
2:12 pm-8:07 pm
1 stop7h 55m
$251
PortlandChicago
PDX - MDW
PDXMDW
Portland
Mon 4/13
12:30 am-8:46 am
1 stop6h 16m
Chicago Midway
Sat 4/18
2:12 pm-8:07 pm
1 stop7h 55m
$251
PortlandChicago
PDX - MDW
PDXMDW
Portland
Tue 3/31
11:15 pm-8:53 am
1 stop7h 38m
Chicago Midway
Wed 4/8
2:05 pm-8:25 pm
1 stop8h 20m
$251
PortlandChicago
PDX - MDW
PDXMDW
Portland
Wed 4/8
5:40 am-11:35 am
Nonstop3h 55m
Chicago Midway
Wed 4/8
5:35 pm-11:00 pm
1 stop7h 25m
$258
PortlandChicago
PDX - MDW
PDXMDW
Portland
Tue 5/5
11:55 pm-5:50 am
Nonstop3h 55m
Chicago Midway
Thu 5/7
5:25 am-10:55 am
1 stop7h 30m
$259
PortlandChicago
PDX - MDW
PDXMDW
Portland
Tue 3/17
7:00 pm-5:45 am
1 stop8h 45m
Chicago Midway
Thu 3/19
10:20 pm-12:45 am
Nonstop4h 25m
$259
Showing 1-10 of 17 results
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 February.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy1 star | 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
What is the cheapest month to book a flight from Portland to Chicago Midway Airport?
Currently, April is the cheapest month in which you can book a flight from Portland to Chicago Midway Airport (average of $132). Flying from Portland to Chicago Midway Airport in March is currently the most expensive (average of $292). 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 February 21, 2026.
It’s typically best to fly out from Portland to Chicago Midway Airport at noon. Doing so could potentially save you 14% 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 February 21, 2026.
Read reviews from past customers who have flown Southwest and Delta 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.
Boarding
8.1
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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Top 2 airlines flying from Portland to Midway
Discover the top 2 airlines 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 February 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$231 | Average$376 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$268 | Average$377 | FlexibilityNo cancel fee | On-timeN/A |