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$153+ 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 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PDX
Jun 13 — Jun 201
Sat 6/13
Sat 6/20
1 adult, Economy
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Cheap 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 May 14, 2026.

This Southwest deal was found by Cheapflights users on 5/13. 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.
Fri 7/34:40 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Tue 7/711:30 pm
PDX
-
MDW
Nonstop3h 50m
Southwest
Deal found 5/13$310
This Southwest deal was found by Cheapflights users on 5/12. 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.
Sat 6/138:25 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Sat 6/2011:30 pm
PDX
-
MDW
Nonstop3h 50m
Southwest
Deal found 5/12$315
This Southwest deal was found by Cheapflights users on 5/13. 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.
Fri 7/34:40 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Sun 7/1211:30 pm
PDX
-
MDW
Nonstop3h 50m
Southwest
Deal found 5/13$321
This Southwest deal was found by Cheapflights users on 5/13. 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.
Fri 7/249:35 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Wed 7/2911:30 pm
PDX
-
MDW
Nonstop3h 50m
Southwest
Deal found 5/13$326
This Southwest deal was found by Cheapflights users on 5/10. 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.
Sat 6/272:35 pm
MDW
-
PDX
1 stop7h 05m
Southwest
Fri 7/311:30 pm
PDX
-
MDW
Nonstop3h 50m
Southwest
Deal found 5/10$330
This Southwest deal was found by Cheapflights users on 5/12. 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 7/34:40 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Fri 7/106:00 pm
PDX
-
MDW
1 stop9h 25m
Southwest
Deal found 5/12$331
This Delta deal was found by Cheapflights users on 5/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/81:52 pm
MDW
-
PDX
1 stop8h 25m
Delta
Mon 8/1012:32 am
PDX
-
MDW
1 stop6h 08m
Delta
Deal found 5/12$335
This Southwest deal was found by Cheapflights users on 5/12. 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 7/179:35 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Mon 7/2711:30 pm
PDX
-
MDW
Nonstop3h 50m
Southwest
Deal found 5/12$337

Find 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 May 14, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$310
(Southwest)

One-way from

$153
(Kiwi.com)

Popular in

June

Cheapest in

March

Average price

$371

Good round-trip deal

$305 or less

Good one-way deal

$163 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. 10% potential increase in price ($45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($15 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 Chicago Midway to Portland.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Portland.
Search Deals

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 May 14, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Portland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 9/9

8:55 pm-11:10 pm

Nonstop4h 15m

Portland

Wed 9/30

10:55 am-4:55 pm

Nonstop4h 00m

$315

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 7/3

9:35 pm-11:55 pm

Nonstop4h 20m

Portland

Sun 7/12

9:45 pm-5:45 am

1 stop6h 00m

$331
Quickest round-trip

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 7/17

9:35 pm-11:55 pm

Nonstop4h 20m

Portland

Thu 7/23

11:30 pm-5:20 am

Nonstop3h 50m

$337

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Thu 7/16

9:35 pm-11:55 pm

Nonstop4h 20m

Portland

Mon 7/20

11:30 pm-5:20 am

Nonstop3h 50m

$337

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Thu 9/10

6:15 am-2:45 pm

2 stops10h 30m

Portland

Tue 9/15

11:30 pm-5:25 am

Nonstop3h 55m

$341

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Thu 7/16

7:06 pm-11:18 pm

1 stop6h 12m

Portland

Mon 7/20

11:15 pm-9:08 am

1 stop7h 53m

$357

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Thu 7/16

7:06 pm-11:18 pm

1 stop6h 12m

Portland

Wed 7/22

12:33 am-8:37 am

1 stop6h 04m

$357

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 6/5

6:40 pm-1:20 am

1 stop8h 40m

Portland

Tue 6/9

6:00 am-11:50 am

Nonstop3h 50m

$367

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sun 7/19

9:45 pm-12:05 am

Nonstop4h 20m

Portland

Sun 7/26

9:45 pm-5:45 am

1 stop6h 00m

$377

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 7/17

10:00 am-4:55 pm

2 stops8h 55m

Portland

Sun 7/19

9:00 pm-6:00 am

1 stop7h 00m

$382

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/13

Showing 1-10 of 23 resultsSorted by cheapest first
1
2
3

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapTicketsDealPrice Accuracy1 starTrust 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Portland flight deals on Cheapflights vs. FlightHub >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 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 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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Portland (average of $227). Flying from Chicago Midway Airport to Portland in June is currently the most expensive (average of $542). 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 May 14, 2026.

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 morning tend to be the most expensive. A flight in the evening could potentially save you up to 7% on airfare.

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

The best insider tips for Chicago Midway Airport to Portland 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 Chicago Midway Airport to Portland 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 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 May 14, 2026.
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
4,299 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

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
4,299 reviews
Southwest
8.0
Very good
4,299 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Boarding

8.1

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 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 1 inbound flight 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 4h 15m. The time it takes to get you to your destination is usually consistent. The distance between Chicago Midway Airport and Portland is about 1746 mi. Generally, flights for this route are nonstop.

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

    According to our current data, Southwest ($227), offers the cheapest pricing from Chicago Midway Airport to Portland. Southwest is currently priced 39% 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 $245, our data shows the cheapest flight currently is $152. When looking at the most popular route, (Chicago Midway - Portland), you can expect to pay $310 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, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Portland (average of $227). Flying from Chicago Midway Airport to Portland in June is currently the most expensive (average of $542). 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
Beaverton
Seaside
Vancouver
Lincoln City
Longview
Lake Oswego
Hillsboro
Clackamas
Troutdale
Cannon Beach
Long Beach
McMinnville
Tigard
The Dalles
Wilsonville
Depoe Bay
Stevenson
Tillamook
Astoria
Gresham

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Alternative routes for Midway to Portland

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Portland flights
O'Hare Intl to Boise flights
O'Hare Intl to Eugene flights
Midway to Medford flights
O'Hare Intl to North Bend flights

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 May 14, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$227Average$358FlexibilityNo cancel feeOn-time63%

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