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$97+ Cheap flights from Midway (MDW) to Portland (PDX)

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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PDX
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from Midway to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Portland (PDX). 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 14, 2025.

Round-trip from

$176
(FlightHub)

One-way from

$97
(Kiwi.com)

Popular in

October

Cheapest in

January

Average price

$368

Good round-trip deal

$166 or less

Good one-way deal

$98 or less
From Chicago Midway to Portland
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One-way flight from Chicago Midway to Portland
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Highest demand for flights based on searches. 12% potential increase in price ($59 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 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 Chicago Midway to Portland.
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Price to beat on a one-way flight from Chicago Midway to Portland.
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Find flight deals from Midway to Portland

Cheapest flights from Midway to Portland
Explore the most affordable flight options available from Midway to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/54:48 pmMDW - PDX
1 stop9h 24mFrontier
Mon 9/156:05 amPDX - MDW
1 stop7h 48mFrontier
Deal found 8/14$176
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/54:48 pmMDW - PDX
1 stop9h 24mFrontier
Sun 9/710:27 amPDX - MDW
1 stop9h 31mFrontier
Deal found 8/13$203
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.
Sun 8/318:55 amMDW - PDX
Nonstop4h 15mSouthwest
Sat 9/66:00 amPDX - MDW
Nonstop4h 00mSouthwest
Deal found 8/13$205
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 10/253:45 pmMDW - PDX
Nonstop4h 20mSouthwest
Fri 10/3110:15 amPDX - MDW
1 stop9h 15mSouthwest
Deal found 8/13$213
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.
Sat 10/253:00 pmMDW - PDX
1 stop7h 26mDelta
Thu 10/3012:40 amPDX - MDW
1 stop6h 15mDelta
Deal found 8/13$223
This Southwest deal was found by Cheapflights users on 8/12. 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 10/249:30 pmMDW - PDX
Nonstop4h 25mSouthwest
Fri 10/316:00 amPDX - MDW
1 stop7h 50mSouthwest
Deal found 8/12$224
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.
Sat 9/272:10 pmMDW - PDX
Nonstop4h 15mSouthwest
Wed 10/16:00 amPDX - MDW
Nonstop4h 00mSouthwest
Deal found 8/14$227
This Southwest deal was found by Cheapflights users on 8/12. 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 9/98:30 amMDW - PDX
Nonstop4h 20mSouthwest
Wed 9/101:30 pmPDX - MDW
Nonstop4h 00mSouthwest
Deal found 8/12$231

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Portland 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 14, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Portland that are best for you.

Fly from

Midway

Fly to

Portland

Route

Depart

Return

Price

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 9/5

4:48 pm-12:12 am

1 stop9h 24m

Portland

Mon 9/15

6:05 am-3:53 pm

1 stop7h 48m

$176

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 9/12

4:48 pm-12:12 am

1 stop9h 24m

Portland

Sun 9/14

10:17 am-9:58 pm

1 stop9h 41m

$203

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 9/5

4:48 pm-12:12 am

1 stop9h 24m

Portland

Sun 9/7

10:27 am-9:58 pm

1 stop9h 31m

$203

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sun 8/31

8:55 am-11:10 am

Nonstop4h 15m

Portland

Sat 9/6

6:00 am-12:00 pm

Nonstop4h 00m

$205

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 9/26

4:48 pm-12:12 am

1 stop9h 24m

Portland

Sun 9/28

10:17 am-9:58 pm

1 stop9h 41m

$212

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 10/25

3:45 pm-6:05 pm

Nonstop4h 20m

Portland

Fri 10/31

10:15 am-9:30 pm

1 stop9h 15m

$213

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Mon 9/29

7:03 pm-7:23 pm

1 stop26h 20m

$97

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 10/31

5:40 am-10:30 am

1 stop6h 50m

$99

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Mon 9/22

4:48 pm-12:12 am

1 stop9h 24m

$109

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 10/29

8:25 pm-10:50 pm

Nonstop4h 25m

$114

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 13 results
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The best insider tips for Chicago Midway Airport to Portland 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 Chicago Midway Airport to Portland trip
Airports
MDW

Use the airport’s mobile system to order food directly to your gate, saving time and ensuring you don’t miss boarding.

Read more about MDWby Ramsey Qubein
PDX

Take the MAX red line from PDX to Downtown Portland; it’s inexpensive and takes about 40 minutes.

Read more about PDXby Brandon Schultz
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 Midway to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Midway 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 Chicago Midway Airport to Portland

What is the cheapest month to book a flight from Chicago Midway Airport to Portland?

Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Portland (average of $277). Flying from Chicago Midway Airport to Portland in March is currently the most expensive (average of $369). 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 MDW to PDX?

Find hourly flight availability from Midway to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 14, 2025.

One of the essential ways to save on airfare from Chicago Midway Airport to Portland is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 21% on airfare.

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated August 14, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Portland, such as Southwest and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Frontier
5.8
Fair
3,217 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Midway to Portland. 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 into for flights to Portland from Chicago Midway?

    Most people fly into Portland (PDX) if they book a flight to Portland from Chicago Midway. On average, Portland has 2 inbound flights from Chicago Midway per day from 2 airlines. Portland is conveniently located just 6.0 mi from Portland’s city center.

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

    According to our current data, Frontier ($108), and Southwest ($238) offers the cheapest pricing from Chicago Midway Airport to Portland. Frontier is currently priced 74% below the average price you’ll pay for this route.

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

    While on average a flight from Chicago Midway Airport to Portland is generally $219, our data shows the cheapest flight currently is $98. When looking at the most popular route, (Chicago Midway - Portland), you can expect to pay $213 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Portland 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 Chicago Midway Airport to Portland?

    Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Portland (average of $277). Flying from Chicago Midway Airport to Portland in March is currently the most expensive (average of $369). 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 Portland?

Book flights to Portland if you plan to visit one of these locations
Vancouver
Seaside
Beaverton
Clackamas
McMinnville
Lake Oswego
Hillsboro
Lincoln City
Cannon Beach
Long Beach
Longview
Tigard
Depoe Bay
Stevenson
Woodburn
Wilsonville
Pacific City
Troutdale
Tillamook
Gresham

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Top 2 airlines flying from Midway to Portland

Discover the top 2 airlines that operate flights from Midway to Portland. 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 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$191FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$238Average$433FlexibilityNo cancel feeOn-time63%

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