HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$123+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — MDW
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Portland to Midway with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 December 18, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$232
(Kissandfly.com)

One-way from

$123
(Delta)

Popular in

January

Cheapest in

May

Average price

$576
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
High demand for flights, 34% potential price rise
Search Deals
Best time to find cheap flights, 10% potential price drop
Search Deals
Average for round-trip flights in December 2024
Search Deals

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 December 18, 2024.

This Frontier deal was found by Cheapflights users on 12/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/301:05 pmPDX - MDW
1 stop6h 04mFrontier
Sat 1/47:00 amMDW - PDX
1 stop10h 44mFrontier
Deal found 12/17$298
This Southwest deal was found by Cheapflights users on 12/18. 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.
Mon 12/304:35 pmPDX - MDW
1 stop7h 05mSouthwest
Sun 1/56:50 pmMDW - PDX
Nonstop4h 30mSouthwest
Deal found 12/18$518
This Delta deal was found by Cheapflights users on 12/17. 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.
Tue 12/1711:13 pmPDX - MDW
1 stop7h 45mDelta
Wed 12/2511:48 amMDW - PDX
1 stop10h 33mDelta
Deal found 12/17$839

Find flights from Portland to Midway within your budget

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 December 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 1/9

4:53 pm-11:51 am

2 stops16h 58m

Chicago Midway

Wed 1/15

1:26 pm-6:21 pm

1 stop6h 55m

$232

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 1/15

9:00 am-2:55 pm

Nonstop3h 55m

Chicago Midway

Wed 1/22

8:30 am-10:55 am

Nonstop4h 25m

$233

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 1/9

10:37 am-11:48 am

1 stop23h 11m

Chicago Midway

Wed 1/15

8:15 am-10:54 pm

3 stops16h 39m

$236

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 3/12

6:15 am-2:15 pm

1 stop6h 00m

Chicago Midway

Sat 3/15

11:15 am-6:19 pm

1 stop9h 04m

$246

PortlandChicago

PDX - MDW

PDXMDW

Portland

Mon 2/24

12:59 am-9:35 am

1 stop6h 36m

$123

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 1/31

9:00 am-2:55 pm

Nonstop3h 55m

$125

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 3/7

6:45 am-12:17 am

1 stop15h 32m

$126

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 3/6

11:16 am-10:09 am

2 stops20h 53m

$161

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 3/5

7:20 am-5:36 pm

3 stops32h 16m

$380

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*1 star

*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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 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 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.

Travel insights for flights from Portland to Midway

Get recent, data-driven insights about flights from Portland to Midway including ideal travel times, pricing trends, and more.

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 October is currently the most expensive (average of $232). 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 December 18, 2024.

It’s typically best to fly out from Portland to Chicago Midway Airport in the evening. Doing so could potentially save you 31% on the flight price compared to flying at noon, which is usually more expensive.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 December 18, 2024.
To help decide which airline to fly from Portland to Chicago, see what other customers have to say about Frontier, Southwest and Delta. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Allegiant Air
7.4
Good
829 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.1
Okay
3,479 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 3 different airlines.

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

    Currently priced at $232, 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 $246, respectively. These flights start at 42% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Portland to Chicago Midway Airport one-way?

    The cheapest airlines for a one-way flight from Portland to Chicago Midway Airport are Delta ($123), Southwest ($125), and Frontier ($126).

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

    Looking at all options, your cheapest flight can be booked for $198. While the most popular route (Portland - Chicago Midway) can be booked for $138 on average our data indicates $394 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 October is currently the most expensive (average of $232). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$134Average$284FlexibilityNo cancel feeOn-time62%
DeltaCheapest$216Average$455FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$233Average$551FlexibilityNo cancel feeOn-time63%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.