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$116+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MDW
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
1 adult, Economy
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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 November 20, 2025.

This Southwest deal was found by Cheapflights users on 11/18. 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 12/95:55 amPDX - MDW
1 stop8h 00mSouthwest
Fri 12/126:35 pmMDW - PDX
1 stop7h 40mSouthwest
Deal found 11/18$246
This Delta deal was found by Cheapflights users on 11/20. 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.
Thu 12/1111:20 pmPDX - MDW
1 stop7h 34mDelta
Sat 12/131:50 pmMDW - PDX
1 stop9h 02mDelta
Deal found 11/20$247
This Delta deal was found by Cheapflights users on 11/19. 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 12/812:32 amPDX - MDW
1 stop6h 47mDelta
Wed 12/171:50 pmMDW - PDX
1 stop9h 02mDelta
Deal found 11/19$249
This Southwest deal was found by Cheapflights users on 11/17. 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.
Mon 12/228:55 pmPDX - MDW
1 stop10h 25mSouthwest
Tue 1/65:35 pmMDW - PDX
1 stop6h 40mSouthwest
Deal found 11/17$252
This Southwest deal was found by Cheapflights users on 11/20. 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.
Fri 12/123:55 pmPDX - MDW
1 stop6h 10mSouthwest
Thu 12/185:15 pmMDW - PDX
1 stop9h 05mSouthwest
Deal found 11/20$256
This Kiwi.com deal was found by Cheapflights users on 11/18. 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.
Thu 12/412:51 pmPDX - MDW
1 stop20h 17mFrontier
Fri 12/52:59 pmMDW - PDX
2 stops19h 54mFrontier
Deal found 11/18$261
This Delta deal was found by Cheapflights users on 11/19. 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.
Thu 11/271:00 pmPDX - MDW
1 stop8h 40mDelta
Wed 12/312:50 pmMDW - PDX
1 stop8h 45mDelta
Deal found 11/19$268
This Southwest deal was found by Cheapflights users on 11/20. 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.
Fri 12/126:30 amPDX - MDW
Nonstop3h 55mSouthwest
Mon 12/154:50 pmMDW - PDX
Nonstop4h 30mSouthwest
Deal found 11/20$273
This Southwest deal was found by Cheapflights users on 11/20. 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.
Thu 12/117:15 amPDX - MDW
1 stop7h 50mSouthwest
Sat 12/139:40 amMDW - PDX
Nonstop4h 35mSouthwest
Deal found 11/20$293

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 November 20, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$246
(Southwest)

One-way from

$116
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$366

Good round-trip deal

$287 or less

Good one-way deal

$186 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 ($35 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($27 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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.
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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 November 20, 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

Fri 12/12

3:55 pm-12:05 am

1 stop6h 10m

Chicago Midway

Mon 12/15

4:50 pm-7:20 pm

Nonstop4h 30m

$247

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 1/8

7:37 pm-8:52 am

2 stops11h 15m

Chicago Midway

Wed 1/14

1:49 pm-12:17 am

2 stops12h 28m

$262

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 3/14

7:25 pm-5:35 am

1 stop8h 10m

Chicago Midway

Wed 3/18

5:45 am-2:30 pm

2 stops10h 45m

$282

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 1/3

6:15 am-5:19 pm

1 stop9h 04m

Chicago Midway

Sat 1/10

6:45 am-4:30 pm

2 stops11h 45m

$284

PortlandChicago

PDX - MDW

PDXMDW

Portland

Mon 12/8

11:20 pm-8:54 am

1 stop7h 34m

Chicago Midway

Thu 12/11

10:49 am-7:35 pm

1 stop10h 46m

$295

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sun 2/1

6:45 am-12:40 pm

Nonstop3h 55m

Chicago Midway

Thu 2/5

8:40 pm-11:15 am

2 stops16h 35m

$314

PortlandChicago

PDX - MDW

PDXMDW

Portland

Mon 3/23

12:55 am-8:54 am

1 stop5h 59m

Chicago Midway

Wed 3/25

2:00 pm-8:30 pm

1 stop8h 30m

$323

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sun 12/21

8:00 pm-5:05 am

1 stop7h 05m

Chicago Midway

Tue 1/6

3:35 pm-6:00 pm

Nonstop4h 25m

$332

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 12/9

12:32 am-9:19 am

1 stop6h 47m

Chicago Midway

Mon 12/15

1:14 pm-10:40 pm

2 stops11h 26m

$337

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 3/10

9:30 am-8:25 pm

1 stop8h 55m

$118

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

Showing 1-10 of 19 results
1
2

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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
Trip.comPrice Accuracy2 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 CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on Portland-Chicago Midway Airport flight deals on Cheapflights vs. CheapOair >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 CheapOair the most. CheapOair 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, April is the cheapest month in which you can book a flight from Portland to Chicago Midway Airport (average of $137). Flying from Portland to Chicago Midway Airport in March is currently the most expensive (average of $316). 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 November 20, 2025.

It’s typically best to fly out from Portland to Chicago Midway Airport at noon. Doing so could potentially save you 38% 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

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

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 November 20, 2025.
Read reviews from past customers who have flown Alaska Airlines, 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.
Alaska Airlines
8.0
Very good
11,325 reviews

Food

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Marcie,Nov 2025

PIT - SEA

It was not a full flight, so I was able to enjoy a row to myself. Luck of the draw, I guess.
Alaska Airlines
8.0
Very good
11,325 reviews
Alaska Airlines
8.0
Very good
11,325 reviews

Food

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Marcie,Nov 2025

PIT - SEA

It was not a full flight, so I was able to enjoy a row to myself. Luck of the draw, I guess.
Southwest
8.0
Very good
4,251 reviews
Alaska Airlines
8.0
Very good
11,325 reviews

Food

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Marcie,Nov 2025

PIT - SEA

It was not a full flight, so I was able to enjoy a row to myself. Luck of the draw, I guess.
Delta
7.9
Good
8,002 reviews
Alaska Airlines
8.0
Very good
11,325 reviews

Food

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Marcie,Nov 2025

PIT - SEA

It was not a full flight, so I was able to enjoy a row to myself. Luck of the draw, I guess.
Frontier
5.8
Fair
3,104 reviews
Alaska Airlines
8.0
Very good
11,325 reviews

Food

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Marcie,Nov 2025

PIT - SEA

It was not a full flight, so I was able to enjoy a row to myself. Luck of the draw, I guess.

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 are 0 flights from Portland to Chicago Midway per day from 4 different airlines.

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

    A quick flight from Portland to Chicago Midway Airport can take about 6h 10m. Southwest provides one of the quickest options available for as low as $247. The distance between Portland and Chicago Midway Airport is about 1746 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Portland to Chicago Midway Airport round-trip?

    Currently priced at $128, Frontier will fly you from Portland to Chicago Midway Airport and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Alaska Airlines and Southwest - these airlines can fly you to your destination from $197 and $246, respectively. These flights start at 65% 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 $94. While the most popular route (Portland - Chicago Midway) can be booked for $179 on average, our data indicates $326 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 $137). Flying from Portland to Chicago Midway Airport in March is currently the most expensive (average of $316). 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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Top 4 airlines flying from Portland to Midway

Discover the top 4 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 November 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$128Average$324FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$197Average$281FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$246Average$404FlexibilityNo cancel feeOn-time63%
DeltaCheapest$268Average$418FlexibilityNo cancel feeOn-timeN/A

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