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Midway

$110+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MDW
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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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 September 17, 2025.

Round-trip from

$195
(Delta)

One-way from

$110
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$361

Good round-trip deal

$312 or less

Good one-way deal

$198 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. 5% potential increase in price ($22 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($26 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 17, 2025.

This Delta deal was found by Cheapflights users on 9/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1710:58 pmPDX - MDW
1 stop7h 42mDelta
Sat 10/183:00 pmMDW - PDX
1 stop7h 26mDelta
Deal found 9/17$195
This Southwest deal was found by Cheapflights users on 9/16. 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 10/226:15 amPDX - MDW
1 stop11h 05mSouthwest
Thu 10/306:25 pmMDW - PDX
1 stop7h 40mSouthwest
Deal found 9/16$200
This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/17:15 amPDX - MDW
2 stops21h 56mFrontier
Fri 10/34:48 pmMDW - PDX
1 stop9h 24mFrontier
Deal found 9/15$204
This Southwest deal was found by Cheapflights users on 9/15. 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 11/186:15 amPDX - MDW
Nonstop3h 55mSouthwest
Mon 11/249:50 pmMDW - PDX
Nonstop4h 30mSouthwest
Deal found 9/15$209
This Booking.com deal was found by Cheapflights users on 9/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/612:52 pmPDX - MDW
1 stop20h 38mFrontier
Sun 11/912:30 pmMDW - PDX
1 stop25h 26mFrontier
Deal found 9/15$213
This Southwest deal was found by Cheapflights users on 9/17. 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.
Fri 10/316:00 amPDX - MDW
1 stop7h 50mSouthwest
Wed 11/54:50 pmMDW - PDX
Nonstop4h 30mSouthwest
Deal found 9/17$219
This Southwest deal was found by Cheapflights users on 9/17. 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.
Wed 10/296:00 amPDX - MDW
Nonstop3h 55mSouthwest
Sat 11/13:45 pmMDW - PDX
Nonstop4h 20mSouthwest
Deal found 9/17$231
This Southwest deal was found by Cheapflights users on 9/17. 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.
Fri 10/316:00 amPDX - MDW
1 stop7h 50mSouthwest
Sun 11/29:50 pmMDW - PDX
Nonstop4h 30mSouthwest
Deal found 9/17$232
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/3110:02 pmPDX - MDW
1 stop14h 55mFrontier
Mon 11/312:30 pmMDW - PDX
1 stop25h 26mFrontier
Deal found 9/16$233

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 September 17, 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

Wed 11/12

12:35 am-9:01 am

1 stop6h 26m

Chicago Midway

Tue 11/18

1:47 pm-8:47 pm

1 stop9h 00m

$264

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 10/14

6:15 am-7:20 pm

1 stop11h 05m

Chicago Midway

Sat 10/18

5:15 am-2:40 pm

1 stop11h 25m

$267

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 12/5

5:30 am-4:20 pm

1 stop8h 50m

Chicago Midway

Mon 12/8

5:15 pm-10:30 pm

1 stop7h 15m

$276

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 12/10

11:15 pm-8:54 am

1 stop7h 39m

Chicago Midway

Mon 12/15

1:50 pm-8:53 pm

1 stop9h 03m

$290

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 10/28

10:10 pm-9:45 am

1 stop9h 35m

Chicago Midway

Tue 11/4

6:00 am-1:00 pm

1 stop9h 00m

$290

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 11/1

5:05 am-4:25 pm

1 stop9h 20m

Chicago Midway

Thu 11/6

9:50 pm-12:20 am

Nonstop4h 30m

$292

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 11/14

12:45 pm-10:40 pm

1 stop7h 55m

Chicago Midway

Mon 11/17

3:15 pm-10:30 pm

1 stop9h 15m

$296

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 10/31

5:50 am-11:45 am

Nonstop3h 55m

Chicago Midway

Mon 11/3

4:50 pm-7:20 pm

Nonstop4h 30m

$297

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 10/22

6:00 am-4:09 pm

1 stop8h 09m

Chicago Midway

Wed 10/29

6:00 am-1:00 pm

1 stop9h 00m

$313

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 10/31

6:00 am-3:50 pm

1 stop7h 50m

Chicago Midway

Wed 11/5

12:05 pm-9:25 pm

2 stops11h 20m

$327

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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

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 September 17, 2025.

It’s typically best to fly out from Portland to Chicago Midway Airport at noon. Doing so could potentially save you 9% 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 September 17, 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
4,242 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

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
Delta
8.0
Very good
7,961 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

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
Frontier
5.8
Fair
3,173 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

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 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 2 flights from Portland to Chicago Midway per day from 3 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 26m. Delta provides one of the quickest options available for as low as $264. 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 $108, 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 Southwest and Delta - these airlines can fly you to your destination from $233 and $256, respectively. These flights start at 71% 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 $123. While the most popular route (Portland - Chicago Midway) can be booked for $190 on average, our data indicates $312 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
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Top 3 airlines flying from Portland to Midway

Discover the top 3 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$324FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$233Average$413FlexibilityNo cancel feeOn-time63%
DeltaCheapest$256Average$377FlexibilityNo cancel feeOn-timeN/A

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