$116 Cheap Flights from Chicago (MDW) to Portland (PDX)

View $116 flight on Sat, Jan 17, 2026Opens in a new window

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

Cheap Flights from Chicago to Portland (MDW-PDX)

Prices were available within the past 7 days and start at $116 for one-way flights and $118 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Thu, Oct 30 - Sat, Nov 15
MDW
Chicago
PDX
Portland
$118 Roundtrip, found 21 hours ago
$118
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Thu, Oct 30 from Chicago to Portland, returning Sat, Nov 15, priced at $118 found 21 hours ago
Frontier Airlines
Fri, Oct 31 - Sat, Nov 15
MDW
Chicago
PDX
Portland
$149 Roundtrip, found 1 day ago
$149
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Oct 31 from Chicago to Portland, returning Sat, Nov 15, priced at $149 found 1 day ago
Frontier Airlines
Thu, Oct 30 - Sun, Nov 16
MDW
Chicago
PDX
Portland
$170 Roundtrip, found 21 hours ago
$170
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Thu, Oct 30 from Chicago to Portland, returning Sun, Nov 16, priced at $170 found 21 hours ago
Frontier Airlines
Fri, Oct 24 - Sat, Nov 1
MDW
Chicago
PDX
Portland
$180 Roundtrip, found 5 days ago
$180
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, Oct 24 from Chicago to Portland, returning Sat, Nov 1, priced at $180 found 5 days ago
Frontier Airlines
Fri, Oct 24 - Sat, Nov 15
MDW
Chicago
PDX
Portland
$190 Roundtrip, found 21 hours ago
$190
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Fri, Oct 24 from Chicago to Portland, returning Sat, Nov 15, priced at $190 found 21 hours ago
Southwest Airlines
Wed, Feb 4 - Sat, Feb 7
MDW
Chicago
PDX
Portland
$197 Roundtrip, found 2 days ago
$197
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Feb 4 from Chicago to Portland, returning Sat, Feb 7, priced at $197 found 2 days ago
Frontier Airlines
Fri, Oct 31 - Sun, Nov 16
MDW
Chicago
PDX
Portland
$201 Roundtrip, found 1 day ago
$201
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Oct 31 from Chicago to Portland, returning Sun, Nov 16, priced at $201 found 1 day ago
Southwest Airlines
Sat, Nov 1 - Wed, Nov 5
MDW
Chicago
PDX
Portland
$207 Roundtrip, found 2 days ago
$207
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Nov 1 from Chicago to Portland, returning Wed, Nov 5, priced at $207 found 2 days ago
Southwest Airlines
Wed, Jan 14 - Sat, Jan 17
MDW
Chicago
PDX
Portland
$212 Roundtrip, found 4 days ago
$212
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Jan 14 from Chicago to Portland, returning Sat, Jan 17, priced at $212 found 4 days ago
Delta
Sat, Nov 8 - Tue, Nov 25
MDW
Chicago
PDX
Portland
$242 Roundtrip, found 2 days ago
$242
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Nov 8 from Chicago to Portland, returning Tue, Nov 25, priced at $242 found 2 days ago

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

September is typically the cheapest month to fly

From $137 - $577 per traveler.

Alternative airports near Portland

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Portland Intl. PDX. Cheapest and Closest option available. Average driving time to city center is 17 minutes. Flights from $260
PDX
Portland Intl.
CheapestClosest
Average driving time to city center17 min
Flights from $260
Flights from Chicago (MDW) to Portland (PDX)
Origin airport
Midway Intl.
Destination airport
Portland Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$118
Distance
1746 mi
Average flight time
2 hours 22 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 October. 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 $116 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?
Lock in a cheap one-way flight from $116 or cheap return flight from $118 from Midway Intl. Airport (MDW) to Portland Intl. Airport (PDX) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Portland Intl. Airport (PDX)?
October is the most affordable month to fly from MDW to PDX. Traveling outside of peak seasons is often the key to landing a great deal.
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 Midway Intl. Airport (MDW) to Portland Intl. Airport (PDX)?
To find the cheapest airline flying from MDW to PDX, use Expedia's filter tool. Tailor your search based on your travel needs, such as preferred carriers and cabin class. You can then sort your results by "Price (lowest to highest)" to see the most affordable options first.
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.