$53 Cheap Flights from Chicago (MDW) to Portland (PDX)

View $53 flight on Tue, Sep 23, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Portland International Airport (PDX)

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Cheap Flights from Chicago to Portland (MDW-PDX)

Prices were available within the past 7 days and start at $53 for one-way flights and $119 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Sep 23 - Fri, Sep 26
MDW
Chicago
PDX
Portland
$119 Roundtrip, found 2 days ago
$119
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Sep 23 from Chicago to Portland, returning Fri, Sep 26, priced at $119 found 2 days ago
Southwest Airlines
Mon, Sep 29 - Tue, Sep 30
MDW
Chicago
PDX
Portland
$125 Roundtrip, found 3 days ago
$125
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Mon, Sep 29 from Chicago to Portland, returning Tue, Sep 30, priced at $125 found 3 days ago
Southwest Airlines
Tue, Sep 23 - Fri, Sep 26
MDW
Chicago
PDX
Portland
$129 Roundtrip, found 2 days ago
$129
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Sep 23 from Chicago to Portland, returning Fri, Sep 26, priced at $129 found 2 days ago
Southwest Airlines
Tue, Sep 23 - Fri, Sep 26
MDW
Chicago
PDX
Portland
$134 Roundtrip, found 2 days ago
$134
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Sep 23 from Chicago to Portland, returning Fri, Sep 26, priced at $134 found 2 days ago
Southwest Airlines
Fri, Sep 19 - Tue, Sep 30
MDW
Chicago
PDX
Portland
$139 Roundtrip, found 2 days ago
$139
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Sep 19 from Chicago to Portland, returning Tue, Sep 30, priced at $139 found 2 days ago
Delta
Sat, Sep 6 - Tue, Sep 9
MDW
Chicago
PDX
Portland
$142 Roundtrip, found 2 days ago
$142
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Sep 6 from Chicago to Portland, returning Tue, Sep 9, priced at $142 found 2 days ago
Southwest Airlines
Wed, Sep 17 - Mon, Sep 22
MDW
Chicago
PDX
Portland
$144 Roundtrip, found 3 days ago
$144
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Sep 17 from Chicago to Portland, returning Mon, Sep 22, priced at $144 found 3 days ago
Southwest Airlines
Tue, Sep 2 - Mon, Sep 8
MDW
Chicago
PDX
Portland
$146 Roundtrip, found 5 days ago
$146
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Tue, Sep 2 from Chicago to Portland, returning Mon, Sep 8, priced at $146 found 5 days ago
Southwest Airlines
Fri, Sep 26 - Mon, Sep 29
MDW
Chicago
PDX
Portland
$148 Roundtrip, found 3 days ago
$148
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Fri, Sep 26 from Chicago to Portland, returning Mon, Sep 29, priced at $148 found 3 days ago
Frontier Airlines
Thu, Jul 17 - Sat, Jul 19
MDW
Chicago
PDX
Portland
$209 Roundtrip, found 5 hours ago
$209
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Thu, Jul 17 from Chicago to Portland, returning Sat, Jul 19, priced at $209 found 5 hours ago

Find the cheapest month to fly from Chicago (MDW) to Portland (PDX)

September is typically the cheapest month to fly

From $118 - $446 per traveler.

Graph displaying average flight prices per month

Flights from Chicago (MDW) to Portland (PDX)
Origin airport
Midway Intl.
Destination airport
Portland Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$119
Distance
1746 mi
Average flight time
2 hours 57 mins

Chicago to Portland Flights

The cheapest times to fly from Chicago to Portland

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Portland are during the month of September. You can find some of the cheapest flights from Chicago to Portland with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Portland

Sunday is one of the best days to book for cheap flights from Chicago to Portland: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Portland

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Portland in 2025. You can also book with separate airlines for your outbound and return journeys, from $53 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Portland flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Portland airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Portland Intl. Airport (PDX) cost?
You can score cheap return tickets from Midway Intl. Airport (MDW) to Portland Intl. Airport (PDX) starting from $105. Reserve your seat and be on your way. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines flight leaving MDW on August 6 2025 and touching down at PDX. The price was last updated on July 11 2025 and has not changed since.
What is the cheapest month to fly from MDW to PDX?
The cheapest flights from MDW to PDX are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Midway Intl. Airport (MDW) to Portland Intl. Airport (PDX)?
Fly directly from Midway Intl. Airport (MDW) to Portland Intl. Airport (PDX) on a Southwest Airlines flight.
What is the cheapest airline that flies from MDW to PDX?
Currently, the cheapest carrier offering one-way flights from MDW to PDX is Southwest Airlines. You can take off on this route from $53. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MDW on September 18 2025. Prices were last updated on July 11 2025 and have not changed since.
How many flights per day from Midway Intl. Airport (MDW) to Portland Intl. Airport (PDX)?
On average, you'll only find 1 nonstop flight departing from Midway Intl. Airport (MDW) to Portland Intl. Airport (PDX) per day. If this doesn't fit your travel plans, think about flights with a layover. Just customize your search results on Expedia to include one stop or more to find the next best option.
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to Portland Intl. Airport (PDX)?
Flights between MDW and PDX are busiest at 8 AM. If you want a quieter trip and potentially cheaper prices, look for a departure that's outside typical rush times.
What day of the week has the most flights from MDW to PDX?
If you depart on a Friday, you'll get the largest range of options for flights from Midway Intl. Airport (MDW) to Portland Intl. Airport (PDX).
What is the earliest flight from Midway Intl. Airport (MDW) to Portland Intl. Airport (PDX)?
The first flight of the day jetting off from Midway Intl. Airport (MDW) is at around 8:30AM UTC-6. Board this plane and you'll touch down at Portland Intl. Airport (PDX) at approximately 10:55AM UTC-8. The entire trip takes 4h 25m.
How long does it take to fly from Midway Intl. Airport (MDW) to Portland Intl. Airport (PDX)?
Flights from MDW to PDX have an average travel time of 4 hours and 26 minutes. The total distance between the two airports is 1,750 mi.
What is the best time to fly from Midway Intl. Airport (MDW) to Portland Intl. Airport (PDX)?
To arrive at Portland Intl. Airport (PDX) on time, opt for a flight that takes off from Midway Intl. Airport (MDW) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Portland from Midway Intl. Airport (MDW)?
Browse your flight options from Midway Intl. Airport (MDW) to Portland Intl. Airport (PDX). This is the only Portland airport you can land at if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Portland Intl. Airport (PDX) last-minute?
Booking your plane ticket from MDW to PDX just before your getaway is typically more expensive. However, if you're flexible with your itinerary, you could grab a cheap last-minute fare.
Is it cheaper to book a MDW to PDX flight and hotel package?
Compared with arranging hotels and flights separately, booking a MDW to PDX flight and hotel package with Expedia could result in significant savings. What's more, having everything in one easy place takes the hassle out of travel planning. Just pick your flights and choose from our wide range of stays, then customize your trip with other add-ons like tours and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Portland Intl. Airport (PDX)?
Typically, you can reschedule or cancel your MDW to PDX flight. However, there may be additional fees, especially if you booked over 24 hours ago. Double-check your itinerary for the airline's rules and fees on flight changes, or if you want more details, visit our Customer Service portal.

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*Available to One Key members.