$62 Cheap Flights from Portland (PDX) to Chicago (MDW)

View $62 flight on Wed, Aug 20, 2025Opens in a new window

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

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Cheap Flights from Portland to Chicago (PDX-MDW)

Prices were available within the past 7 days and start at $62 for one-way flights and $105 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Oct 28 - Tue, Nov 4
PDX
Portland
MDW
Chicago
$105 Roundtrip, found 16 hours ago
$105
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Tue, Oct 28 from Portland to Chicago, returning Tue, Nov 4, priced at $105 found 16 hours ago
Southwest Airlines
Tue, Oct 28 - Tue, Nov 4
PDX
Portland
MDW
Chicago
$115 Roundtrip, found 16 hours ago
$115
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Tue, Oct 28 from Portland to Chicago, returning Tue, Nov 4, priced at $115 found 16 hours ago
Southwest Airlines
Tue, Aug 19 - Sat, Aug 30
PDX
Portland
MDW
Chicago
$117 Roundtrip, found 4 days ago
$117
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Aug 19 from Portland to Chicago, returning Sat, Aug 30, priced at $117 found 4 days ago
Southwest Airlines
Fri, Sep 19 - Sat, Sep 27
PDX
Portland
MDW
Chicago
$119 Roundtrip, found 14 hours ago
$119
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Fri, Sep 19 from Portland to Chicago, returning Sat, Sep 27, priced at $119 found 14 hours ago
Southwest Airlines
Tue, Oct 28 - Tue, Nov 4
PDX
Portland
MDW
Chicago
$120 Roundtrip, found 16 hours ago
$120
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Tue, Oct 28 from Portland to Chicago, returning Tue, Nov 4, priced at $120 found 16 hours ago
Southwest Airlines
Tue, Oct 28 - Tue, Nov 4
PDX
Portland
MDW
Chicago
$124 Roundtrip, found 16 hours ago
$124
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Tue, Oct 28 from Portland to Chicago, returning Tue, Nov 4, priced at $124 found 16 hours ago
Southwest Airlines
Tue, Oct 28 - Tue, Nov 4
PDX
Portland
MDW
Chicago
$125 Roundtrip, found 16 hours ago
$125
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Tue, Oct 28 from Portland to Chicago, returning Tue, Nov 4, priced at $125 found 16 hours ago
Southwest Airlines
Tue, Aug 19 - Sat, Aug 30
PDX
Portland
MDW
Chicago
$127 Roundtrip, found 4 days ago
$127
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Aug 19 from Portland to Chicago, returning Sat, Aug 30, priced at $127 found 4 days ago
Delta
Tue, Oct 21 - Wed, Nov 12
PDX
Portland
MDW
Chicago
$151 Roundtrip, found 17 hours ago
$151
Roundtrip
found 17 hours ago
Select Delta flight, departing Tue, Oct 21 from Portland to Chicago, returning Wed, Nov 12, priced at $151 found 17 hours ago
Frontier Airlines
Sun, Sep 21 - Fri, Sep 26
PDX
Portland
MDW
Chicago
$275 Roundtrip, found 21 hours ago
$275
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Sun, Sep 21 from Portland to Chicago, returning Fri, Sep 26, priced at $275 found 21 hours ago

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

October is typically the cheapest month to fly

From $118 - $443 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $274
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $274
Flights from Portland (PDX) to Chicago (MDW)
Origin airport
Portland Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$105
Distance
1746 mi
Average flight time
7 hours 17 mins

Portland to Chicago Flights

The cheapest times to fly from Portland to Chicago

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 Portland to Chicago are during the month of October. You can find some of the cheapest flights from Portland to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Portland to Chicago

Sunday is one of the best days to book for cheap flights from Portland to Chicago: 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 Portland to Chicago

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 Portland to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $62 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 Portland to Chicago 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 Portland to Chicago 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 Portland Intl. Airport (PDX) to Midway Intl. Airport (MDW) cost?
You can score affordable return tickets from Portland Intl. Airport (PDX) to Midway Intl. Airport (MDW) starting from $117. Snag a seat and start your adventure. 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 PDX on August 6 2025 and touching down at MDW. The price was last updated on July 10 2025 and has not changed since.
What is the cheapest month to fly from PDX to MDW?
The cheapest flights from PDX to MDW 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 Portland Intl. Airport (PDX) to Midway Intl. Airport (MDW)?
If you're departing from Portland Intl. Airport (PDX), you can get on a direct flight to Midway Intl. Airport (MDW) with Southwest Airlines.
What is the cheapest airline that flies from PDX to MDW?
Book a flight from PDX to MDW with Southwest Airlines. This airline currently has the cheapest one-way fare on this route, starting at $65. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from PDX on September 27 2025. Prices were last updated on July 10 2025 and have not changed since.
How many flights per day from Portland Intl. Airport (PDX) to Midway Intl. Airport (MDW)?
On average, just 1 direct flight departs each day from Portland Intl. Airport (PDX) to Midway Intl. Airport (MDW). Need more options? Use Expedia's filter tool to discover flights with layovers and add a new stop to your trip.
What are the most popular departure times for flights from Portland Intl. Airport (PDX) to Midway Intl. Airport (MDW)?
Flights between PDX and MDW are busiest at 9 AM. If you're after a more relaxed atmosphere and potentially cheaper tickets, look for a departure outside the usual busy windows.
What day of the week has the most flights from PDX to MDW?
If you travel on a Friday, you'll get the greatest range of choices for flights from Portland Intl. Airport (PDX) to Midway Intl. Airport (MDW).
What is the earliest flight from Portland Intl. Airport (PDX) to Midway Intl. Airport (MDW)?
The first flight of the day out of Portland Intl. Airport (PDX) is at around 8:00AM UTC-8. Catch this flight and you'll reach Midway Intl. Airport (MDW) at approximately 1:55PM UTC-6. The entire trip takes 3h 55m.
How long does it take to fly from Portland Intl. Airport (PDX) to Midway Intl. Airport (MDW)?
The average flight time from PDX to MDW is 3 hours and 55 minutes, covering a total distance of 1,750 mi.
What airline has the least delays from PDX to MDW?
Southwest Airlines has the strongest track record for on-time direct flights from Portland Intl. Airport (PDX) to Midway Intl. Airport (MDW), with an on-time rating of 87%. Use the Expedia App to view your journey status before you take off and get notified of any trip changes.
What is the best time to fly from Portland Intl. Airport (PDX) to Midway Intl. Airport (MDW)?
Book a flight from Portland Intl. Airport (PDX) to Midway Intl. Airport (MDW) that leaves before 3 PM to reduce the risk of delays and cancellations. Departures after this hour are on average 22% more likely to be canceled.**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 Chicago from Portland Intl. Airport (PDX)?
If you're leaving on a direct flight from Portland Intl. Airport (PDX) to Chicago, you can touch down at either O'Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Portland Intl. Airport (PDX) to Midway Intl. Airport (MDW) last-minute?
Booking your plane ticket from PDX to MDW just before your trip is typically more expensive. But if you're flexible with your departure dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a PDX to MDW flight and hotel package?
You'll generally save money by securing a PDX to MDW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one place. After selecting your ideal flights and accommodations, consider adding extras including tours, activities and car rentals.
Can I cancel or change the date of my flight from Portland Intl. Airport (PDX) to Midway Intl. Airport (MDW)?
In most instances, you're able to reschedule or cancel your PDX to MDW flight. However, there may be additional fees, especially if you booked more than 24 hours ago. Double-check your itinerary for the airline's guidelines and fees on flight changes, or if you'd like more information, go to our Customer Service portal.

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