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$114+ Cheap flights from Portland (PDX) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MDW
Aug 16 — Aug 231
Sat 8/16
Sat 8/23
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Chicago Midway are usually found in February or August, booked 35 days in advance, depart on a Friday or Thursday and return on a Saturday

Cheap 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 11, 2025.

Round-trip from

$203
(Southwest)

One-way from

$114
(Southwest)

Popular in

December

Cheapest in

February

Average price

$286

Good round-trip deal

$238 or less

Good one-way deal

$175 or less
From Portland to Chicago Midway
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One-way flight from Portland to Chicago Midway
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Highest demand for flights based on searches. 21% potential increase in price ($113 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($22 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Portland to Chicago Midway.
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Price to beat on a one-way flight from Portland to Chicago Midway.
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Find 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 August 11, 2025.

This Southwest deal was found by Cheapflights users on 8/10. 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.
Sun 8/311:20 pmPDX - MDW
Nonstop3h 55mSouthwest
Tue 9/93:50 pmMDW - PDX
Nonstop4h 15mSouthwest
Deal found 8/10$203
This Southwest deal was found by Cheapflights users on 8/11. 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 8/305:35 amPDX - MDW
1 stop7h 10mSouthwest
Sat 9/68:20 amMDW - PDX
Nonstop4h 15mSouthwest
Deal found 8/11$215
This Southwest deal was found by Cheapflights users on 8/10. 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 9/101:30 pmPDX - MDW
Nonstop4h 00mSouthwest
Tue 9/163:50 pmMDW - PDX
Nonstop4h 15mSouthwest
Deal found 8/10$227
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/226:05 amPDX - MDW
1 stop7h 48mMultiple Airlines
Mon 9/297:03 pmMDW - PDX
1 stop18h 08mMultiple Airlines
Deal found 8/9$234
This Priceline deal was found by Cheapflights users on 8/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/86:05 amPDX - MDW
1 stop7h 48mFrontier
Mon 9/154:48 pmMDW - PDX
1 stop9h 24mFrontier
Deal found 8/11$235
This Southwest deal was found by Cheapflights users on 8/11. 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 9/161:30 pmPDX - MDW
Nonstop4h 00mSouthwest
Sat 9/203:25 pmMDW - PDX
1 stop8h 45mSouthwest
Deal found 8/11$237
This Southwest deal was found by Cheapflights users on 8/10. 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 9/261:35 pmPDX - MDW
Nonstop4h 00mSouthwest
Tue 9/303:50 pmMDW - PDX
Nonstop4h 15mSouthwest
Deal found 8/10$238
This Southwest deal was found by Cheapflights users on 8/11. 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 9/51:35 pmPDX - MDW
Nonstop4h 00mSouthwest
Tue 9/93:50 pmMDW - PDX
Nonstop4h 15mSouthwest
Deal found 8/11$242
This Southwest deal was found by Cheapflights users on 8/8. 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 10/283:10 pmPDX - MDW
1 stop5h 30mSouthwest
Sat 11/13:55 pmMDW - PDX
1 stop8h 20mSouthwest
Deal found 8/8$246

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 11, 2025.
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

Sun 8/31

1:20 pm-7:15 pm

Nonstop3h 55m

Chicago Midway

Tue 9/9

3:50 pm-6:05 pm

Nonstop4h 15m

$203

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 8/30

5:35 am-2:45 pm

1 stop7h 10m

Chicago Midway

Sat 9/6

8:20 am-10:35 am

Nonstop4h 15m

$215

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 9/10

1:30 pm-7:30 pm

Nonstop4h 00m

Chicago Midway

Tue 9/16

3:50 pm-6:05 pm

Nonstop4h 15m

$227

PortlandChicago

PDX - MDW

PDXMDW

Portland

Mon 9/22

6:05 am-3:53 pm

1 stop7h 48m

Chicago Midway

Mon 9/29

7:03 pm-11:11 am

1 stop18h 08m

$234

PortlandChicago

PDX - MDW

PDXMDW

Portland

Mon 9/8

6:05 am-3:53 pm

1 stop7h 48m

Chicago Midway

Mon 9/15

4:48 pm-12:12 am

1 stop9h 24m

$235

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 9/16

1:30 pm-7:30 pm

Nonstop4h 00m

Chicago Midway

Sat 9/20

3:25 pm-10:10 pm

1 stop8h 45m

$237

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 9/26

1:35 pm-7:35 pm

Nonstop4h 00m

Chicago Midway

Tue 9/30

3:50 pm-6:05 pm

Nonstop4h 15m

$238

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 9/5

1:35 pm-7:35 pm

Nonstop4h 00m

Chicago Midway

Tue 9/9

3:50 pm-6:05 pm

Nonstop4h 15m

$242

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 10/28

3:10 pm-10:40 pm

1 stop5h 30m

Chicago Midway

Sat 11/1

3:55 pm-10:15 pm

1 stop8h 20m

$246

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 9/10

1:30 pm-7:30 pm

Nonstop4h 00m

$114

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/11

Showing 1-10 of 21 results
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The best insider tips for Portland to Chicago Midway Airport flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Portland to Chicago Midway Airport trip
Airports
PDX

Expect security wait times up to 15 minutes off-peak, longer during rush hours. Use Express Lanes if eligible for faster processing.

Read more about PDXby Brandon Schultz
MDW

Use the Orange Line train for easy access to downtown Chicago from MDW. It takes less than 30 minutes and is cost-effective.

Read more about MDWby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

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

Brandon Schultz

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

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

How far ahead should I book a flight from Portland to Chicago Midway Airport?

Use this chart to determine the optimal time to book a round-trip flight from Portland to Midway. Price data was last updated on August 8, 2025.

The best time to book flights from Portland to Chicago Midway Airport is 35 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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 $160). Flying from Portland to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 11, 2025.

It’s typically best to fly out from Portland to Chicago Midway Airport in the afternoon. Doing so could potentially save you 36% on the flight price compared to flying in the morning, which is usually more expensive.

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 11, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Frontier 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
4,246 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,978 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.8
Fair
3,222 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 2 different airlines.

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

    Currently priced at $203, 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 50% 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 $98. While the most popular route (Portland - Chicago Midway) can be booked for $132 on average our data indicates $280 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, April is the cheapest month in which you can book a flight from Portland to Chicago Midway Airport (average of $160). Flying from Portland to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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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 August 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$261FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$249Average$432FlexibilityNo cancel feeOn-time63%

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