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Midway

$149+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MDW
Jun 8 — Jun 151
Mon 6/8
Mon 6/15
1 adult, Economy
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Cheap flight deals from Portland to Midway

Cheapest flights from Portland to Midway
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 May 9, 2026.

This Southwest deal was found by Cheapflights users on 5/4. 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 6/35:40 am
PDX
-
MDW
Nonstop3h 55m
Southwest
Wed 6/109:10 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Deal found 5/4$305
This Southwest deal was found by Cheapflights users on 5/8. 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 6/2711:30 pm
PDX
-
MDW
Nonstop3h 50m
Southwest
Wed 7/19:10 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Deal found 5/8$310
This Southwest deal was found by Cheapflights users on 5/6. 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.
Thu 5/283:00 pm
PDX
-
MDW
1 stop6h 55m
Southwest
Sat 6/68:25 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Deal found 5/6$315
This Southwest deal was found by Cheapflights users on 5/6. 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 6/25:40 am
PDX
-
MDW
Nonstop3h 55m
Southwest
Sat 6/68:25 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Deal found 5/6$316
This Southwest deal was found by Cheapflights users on 5/7. 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 5/295:10 am
PDX
-
MDW
Nonstop3h 55m
Southwest
Tue 6/28:50 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Deal found 5/7$321
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1911:30 pm
PDX
-
MDW
Nonstop3h 55m
Southwest
Fri 8/219:00 am
MDW
-
PDX
1 stop8h 00m
Southwest
Deal found 5/4$322
This Delta deal was found by Cheapflights users on 5/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/249:39 pm
PDX
-
MDW
1 stop10h 21m
Delta
Fri 5/291:59 pm
MDW
-
PDX
1 stop8h 12m
Delta
Deal found 5/6$325
This Southwest deal was found by Cheapflights users on 5/8. 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 6/35:40 am
PDX
-
MDW
Nonstop3h 55m
Southwest
Sat 6/68:25 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Deal found 5/8$326
This Southwest deal was found by Cheapflights users on 5/5. 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.
Fri 6/56:00 am
PDX
-
MDW
Nonstop3h 50m
Southwest
Mon 6/89:35 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Deal found 5/5$327

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 May 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$305
(Southwest)

One-way from

$149
(Kiwi.com)

Popular in

May

Cheapest in

January

Average price

$377

Good round-trip deal

$426 or less

Good one-way deal

$188 or less
Provider with most accurate pricing for Portland-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Chicago Midway flights.
Search Deals
From Portland to Chicago Midway
Search Deals
One-way flight from Portland to Chicago Midway
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Portland to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Portland to Chicago Midway.
Search Deals

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 May 9, 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

Price

Cheapest round-trip

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 7/3

12:15 pm-11:25 pm

2 stops9h 10m

Chicago Midway

Sat 7/11

8:25 pm-10:45 pm

Nonstop4h 20m

$320
Quickest round-trip

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 7/21

11:30 pm-5:20 am

Nonstop3h 50m

Chicago Midway

Fri 7/24

4:40 pm-7:00 pm

Nonstop4h 20m

$326

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 5/28

5:10 am-11:05 am

Nonstop3h 55m

Chicago Midway

Wed 6/3

8:50 pm-11:10 pm

Nonstop4h 20m

$336

PortlandChicago

PDX - MDW

PDXMDW

Portland

Mon 6/8

2:05 pm-12:35 am

1 stop8h 30m

Chicago Midway

Fri 6/12

9:35 pm-11:55 pm

Nonstop4h 20m

$337

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 6/2

5:40 am-11:35 am

Nonstop3h 55m

Chicago Midway

Sat 6/6

2:15 pm-9:35 pm

2 stops9h 20m

$352

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 6/24

3:20 pm-12:05 am

1 stop6h 45m

Chicago Midway

Sun 6/28

9:45 pm-12:05 am

Nonstop4h 20m

$357

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sun 6/7

9:45 pm-5:45 am

1 stop6h 00m

Chicago Midway

Wed 6/17

9:10 pm-11:30 pm

Nonstop4h 20m

$361

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 7/17

11:30 pm-5:20 am

Nonstop3h 50m

Chicago Midway

Sun 7/19

5:25 am-1:25 pm

2 stops10h 00m

$362

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 6/27

11:30 pm-5:20 am

Nonstop3h 50m

Chicago Midway

Wed 7/1

9:10 pm-11:30 pm

Nonstop4h 20m

$375

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 6/12

3:15 pm-1:00 am

1 stop7h 45m

Chicago Midway

Fri 6/19

6:40 pm-1:20 am

1 stop8h 40m

$377

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/7

Showing 1-10 of 22 resultsSorted by cheapest first
1
2
3

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • 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.
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, 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 $377). 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 May 9, 2026.

It’s typically best to fly out from Portland to Chicago Midway Airport at noon. Doing so could potentially save you 20% on the flight price compared to flying in the evening, which is usually more expensive.

How much does it cost to fly round-trip from Portland to Chicago Midway Airport?

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
Ramsey Qubein

Ramsey Qubein

Expert on MDW

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Brandon Schultz

Brandon Schultz

Expert on PDX

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more

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 May 9, 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.
Southwest
8.0
Very good
4,302 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,302 reviews
Southwest
8.0
Very good
4,302 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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.

  • What airport do you fly from for flights from Portland to Chicago Midway?

    If you book a flight to Chicago Midway from Portland, you will be flying from Portland, which is the city’s only airport. Portland (PDX) is located 6.0 mi from the center of Portland. There is 1 flight from Portland to Chicago Midway per day from 1 airline.

  • How long is the flight from Portland to Chicago Midway Airport?

    A quick flight from Portland to Chicago Midway Airport can take about 9h 10m. Southwest provides one of the quickest options available for as low as $320. The distance between Portland and Chicago Midway Airport is about 1746 mi.

  • What is the cheapest airline to fly from Portland to Chicago Midway Airport round-trip?

    Currently priced at $217, Southwest will fly you from Portland to Chicago Midway Airport and back. In addition to Southwest, many other airlines offer competitively priced options for your trip. This flight start at 31% lower than the current average price 3 months from now.

  • What are the cheapest flights from Portland to Chicago Midway Airport?

    Looking at all options, your cheapest flight can be booked for $125. While the most popular route (Portland - Chicago Midway) can be booked for $310 on average, our data indicates $382 when flying from Portland to Chicago Midway Airport.

  • Can I find deals for flights from Portland to Midway that include hotel bookings?

    Yes. In addition to deals on Portland to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Midway.

  • Can I find deals for business class flights from Portland to Midway?

    Yes. Cheapflights offers flight deals from Portland to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • 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 $377). 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.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

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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 May 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$217Average$357FlexibilityNo cancel feeOn-time63%

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