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$106+ 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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PDX
Mar 19 — Mar 261
Wed 3/19
Wed 3/26
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 March 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$237
(Southwest)

One-way from

$106
(CheapOair)

Popular in

October

Cheapest in

May

Average price

$506

Good round-trip deal

$354 or less

Good one-way deal

$209 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.
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From Chicago Midway to Portland
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One-way flight from Chicago Midway to Portland
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($90 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($21 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 14, 2025.

This Southwest deal was found by Cheapflights users on 3/11. 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 5/34:15 pmMDW - PDX
Nonstop4h 20mSouthwest
Wed 5/146:35 pmPDX - MDW
1 stop8h 45mSouthwest
Deal found 3/11$237
This Booking.com deal was found by Cheapflights users on 3/12. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/256:40 amMDW - PDX
1 stop19h 57mFrontier
Thu 3/276:32 amPDX - MDW
1 stop15h 45mFrontier
Deal found 3/12$240
This Delta deal was found by Cheapflights users on 3/12. 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 4/265:59 pmMDW - PDX
1 stop6h 36mDelta
Fri 5/212:59 amPDX - MDW
1 stop6h 41mDelta
Deal found 3/12$247

Find flights from Midway to Portland within your budget

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 March 14, 2025.

Fly from

Midway

Fly to

Portland

Route

Depart

Return

Price

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 5/3

4:15 pm-6:35 pm

Nonstop4h 20m

Portland

Wed 5/14

6:35 pm-5:20 am

1 stop8h 45m

$237

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 3/25

6:40 am-12:37 am

1 stop19h 57m

Portland

Thu 3/27

6:32 am-12:17 am

1 stop15h 45m

$240

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 4/26

3:02 pm-10:35 pm

1 stop9h 33m

Portland

Sat 5/3

6:20 am-2:22 pm

1 stop6h 02m

$247

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Thu 5/29

2:44 pm-12:17 am

1 stop11h 33m

$106

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Thu 5/15

3:03 pm-8:58 am

1 stop19h 55m

$109

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 4/23

4:30 pm-6:50 pm

Nonstop4h 20m

$114

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 4/26

3:02 pm-10:35 pm

1 stop9h 33m

$124

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Mon 6/2

9:12 am-12:39 pm

2 stops29h 27m

$167

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/12

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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 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.

Travel insights for flights from Midway to Portland

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

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 $374). 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 March 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 at noon tend to be the most expensive. A flight in the morning could potentially save you up to 37% on airfare.

Rainfall in Portland by month

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

In terms of precipitation, rainfall in Portland ranges from 0.7 - 5.6 inches per month. November is typically the wettest month, when rainfall can reach 5.6 in. July is typically the driest time to visit Portland when rainfall is around 0.7 in.

Temperature in Portland by month

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

If weather is an important factor for your trip to Portland, 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 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 41.0 F).

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 March 14, 2025.
Get a feel of what it's like to fly with Southwest, Delta and Allegiant Air from Chicago to Portland by reading reviews from past customers. 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
4,292 reviews

Crew

8.7

Comfort

8.1

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Southwest
8.1
Very good
4,292 reviews
Southwest
8.1
Very good
4,292 reviews

Crew

8.7

Comfort

8.1

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Delta
8.0
Very good
7,944 reviews
Southwest
8.1
Very good
4,292 reviews

Crew

8.7

Comfort

8.1

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Allegiant Air
7.3
Good
736 reviews
Southwest
8.1
Very good
4,292 reviews

Crew

8.7

Comfort

8.1

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Frontier
6.0
Okay
3,293 reviews
Southwest
8.1
Very good
4,292 reviews

Crew

8.7

Comfort

8.1

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.1

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 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, Southwest ($237), Frontier ($240), and Delta ($247) offers the cheapest pricing from Chicago Midway Airport to Portland. Southwest is currently priced 36% below the average price you’ll pay for this route.

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

    One-way options have recently been found by users for as low as $106 on Frontier. Other airlines that offer cheap prices include Allegiant Air from $109 and Southwest from $114 one-way.

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

    While on average a flight from Chicago Midway Airport to Portland is generally $396, our data shows the cheapest flight currently is $113. When looking at the most popular route, (Chicago Midway - Portland), you can expect to pay $150 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 $374). 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
Lincoln City
Beaverton
Seaside
McMinnville
Lake Oswego
Hillsboro
Vancouver
Gresham
Long Beach
Cannon Beach
Tigard
Astoria
Hood River
Woodburn
Depoe Bay
Pacific City
Stevenson
Troutdale
Longview
Wilsonville

Browse thousands of different options on Cheapflights for your next trip

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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 March 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$179FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$237Average$445FlexibilityNo cancel feeOn-time63%
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