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$119+ 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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PDX
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
1 adult, Economy
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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 November 26, 2025.

This Southwest deal was found by Cheapflights users on 11/24. 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 12/173:10 pmMDW - PDX
1 stop8h 50mSouthwest
Sun 12/285:00 amPDX - MDW
Nonstop3h 55mSouthwest
Deal found 11/24$237
This Southwest deal was found by Cheapflights users on 11/24. 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 12/243:15 pmMDW - PDX
1 stop9h 15mSouthwest
Sun 1/43:00 pmPDX - MDW
1 stop8h 10mSouthwest
Deal found 11/24$246
This Southwest deal was found by Cheapflights users on 11/24. 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 12/198:00 amMDW - PDX
1 stop10h 35mSouthwest
Sun 1/45:00 amPDX - MDW
Nonstop3h 55mSouthwest
Deal found 11/24$247
This Delta deal was found by Cheapflights users on 11/24. 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.
Wed 12/171:50 pmMDW - PDX
1 stop9h 02mDelta
Tue 12/306:15 amPDX - MDW
1 stop9h 04mDelta
Deal found 11/24$308
This Kiwi.com deal was found by Cheapflights users on 11/24. 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.
Fri 12/122:59 pmMDW - PDX
2 stops19h 54mFrontier
Sun 12/147:26 pmPDX - MDW
1 stop17h 26mFrontier
Deal found 11/24$310
This Southwest deal was found by Cheapflights users on 11/24. 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 12/203:45 pmMDW - PDX
2 stops10h 40mSouthwest
Sun 12/215:10 amPDX - MDW
1 stop8h 25mSouthwest
Deal found 11/24$314

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 November 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$232
(Southwest)

One-way from

$119
(Delta)

Popular in

November

Cheapest in

January

Average price

$645

Good round-trip deal

$226 or less

Good one-way deal

$118 or less
Provider with most accurate pricing for Chicago Midway-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Portland flights.
Search Deals
From Chicago Midway to Portland
Search Deals
One-way flight from Chicago Midway to Portland
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($98 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($20 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 Chicago Midway to Portland.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Portland.
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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 November 26, 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

Wed 12/17

3:10 pm-10:00 pm

1 stop8h 50m

Portland

Sun 12/28

5:00 am-10:55 am

Nonstop3h 55m

$237

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 3/10

1:55 pm-10:55 pm

2 stops11h 00m

Portland

Fri 3/13

11:50 am-10:35 pm

2 stops8h 45m

$257

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 3/14

8:10 pm-1:40 am

1 stop7h 30m

Portland

Wed 3/18

11:55 pm-5:45 am

Nonstop3h 50m

$267

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Mon 2/23

4:15 pm-11:00 pm

2 stops8h 45m

Portland

Fri 2/27

6:00 pm-5:15 am

2 stops9h 15m

$267

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 1/10

5:35 am-11:40 am

1 stop8h 05m

Portland

Sat 1/17

8:45 am-6:30 pm

2 stops7h 45m

$268

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 1/7

8:10 am-3:45 pm

1 stop9h 35m

Portland

Sun 1/11

6:45 am-12:40 pm

Nonstop3h 55m

$283

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 3/6

6:05 am-1:45 pm

1 stop9h 40m

Portland

Sun 3/8

11:55 pm-5:45 am

Nonstop3h 50m

$283

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Mon 2/23

1:49 pm-8:30 pm

1 stop8h 41m

Portland

Mon 3/2

7:35 pm-8:53 am

2 stops11h 18m

$296

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 4/7

2:03 pm-9:11 pm

1 stop9h 08m

Portland

Mon 4/13

9:45 pm-9:51 am

1 stop10h 06m

$298

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 12/17

1:50 pm-8:52 pm

1 stop9h 02m

Portland

Tue 12/30

6:15 am-5:19 pm

1 stop9h 04m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/24

Showing 1-10 of 22 results
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Compare providers for flights from Midway to Portland

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 Midway to Portland in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 Chicago Midway Airport-Portland flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Portland flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Portland flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Portland flights, Cheapflights users trust eDreams the most. eDreams 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 Chicago Midway Airport-Portland 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 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, December is the cheapest month in which you can book a flight from Chicago Midway Airport to Portland (average of $145). Flying from Chicago Midway Airport to Portland in June is currently the most expensive (average of $397). 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 November 26, 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 17% on airfare.

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

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 November 26, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Portland, such as Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,254 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 0 inbound flights from Chicago Midway per day from 1 airline. Portland is conveniently located just 6.0 mi from Portland’s city center.

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

    Airlines like Southwest fly from Chicago Midway Airport to Portland in about 8h 50m. The time it takes to get you to your destination can typically vary by up to . The distance between Chicago Midway Airport and Portland is about 1746 mi.

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

    According to our current data, Southwest ($238), offers the cheapest pricing from Chicago Midway Airport to Portland. Southwest is currently priced 45% 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 $356, our data shows the cheapest flight currently is $108. When looking at the most popular route, (Chicago Midway - Portland), you can expect to pay $227 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, December is the cheapest month in which you can book a flight from Chicago Midway Airport to Portland (average of $145). Flying from Chicago Midway Airport to Portland in June is currently the most expensive (average of $397). 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
Clackamas
Lincoln City
Lake Oswego
Beaverton
McMinnville
Hillsboro
Troutdale
Cannon Beach
Long Beach
Longview
Tigard
The Dalles
Depoe Bay
Stevenson
Wilsonville
Pacific City
Gresham
Tillamook

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Midway to Portland

Discover the top airline 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 November 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$238Average$453FlexibilityNo cancel feeOn-time63%

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