$90 Cheap Flights from Portland (PDX) to Chicago (MDW)

View $90 flight on Sat, May 31, 2025Opens in a new window

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

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Find available prices by choosing your travel dates.

Cheap Flights from Portland to Chicago (PDX-MDW)

Prices were available within the past 7 days and start at $90 for one-way flights and $188 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, May 31 - Tue, Jun 3
PDX
Portland
MDW
Chicago
$188 Roundtrip, found 4 hours ago
$188
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, May 31 from Portland to Chicago, returning Tue, Jun 3, priced at $188 found 4 hours ago
Frontier Airlines
Sat, May 31 - Fri, Jun 6
PDX
Portland
MDW
Chicago
$198 Roundtrip, found 4 hours ago
$198
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, May 31 from Portland to Chicago, returning Fri, Jun 6, priced at $198 found 4 hours ago
Delta
Fri, May 30 - Sat, May 31
PDX
Portland
MDW
Chicago
$199 Roundtrip, found 1 hour ago
$199
Roundtrip
found 1 hour ago
Select Delta flight, departing Fri, May 30 from Portland to Chicago, returning Sat, May 31, priced at $199 found 1 hour ago
Southwest Airlines
Sat, May 24 - Tue, May 27
PDX
Portland
MDW
Chicago
$203 Roundtrip, found 10 hours ago
$203
Roundtrip
found 10 hours ago
Select Southwest Airlines flight, departing Sat, May 24 from Portland to Chicago, returning Tue, May 27, priced at $203 found 10 hours ago
Frontier Airlines
Fri, Apr 25 - Mon, Apr 28
PDX
Portland
MDW
Chicago
$208 Roundtrip, found 2 hours ago
$208
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Fri, Apr 25 from Portland to Chicago, returning Mon, Apr 28, priced at $208 found 2 hours ago
Southwest Airlines
Sat, May 31 - Tue, Jun 10
PDX
Portland
MDW
Chicago
$213 Roundtrip, found 8 hours ago
$213
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Sat, May 31 from Portland to Chicago, returning Tue, Jun 10, priced at $213 found 8 hours ago
Southwest Airlines
Mon, May 26 - Sat, May 31
PDX
Portland
MDW
Chicago
$214 Roundtrip, found 4 days ago
$214
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Mon, May 26 from Portland to Chicago, returning Sat, May 31, priced at $214 found 4 days ago
Southwest Airlines
Sat, May 31 - Mon, Jun 9
PDX
Portland
MDW
Chicago
$218 Roundtrip, found 5 hours ago
$218
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Sat, May 31 from Portland to Chicago, returning Mon, Jun 9, priced at $218 found 5 hours ago
Southwest Airlines
Thu, May 29 - Tue, Jun 3
PDX
Portland
MDW
Chicago
$222 Roundtrip, found 2 days ago
$222
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, May 29 from Portland to Chicago, returning Tue, Jun 3, priced at $222 found 2 days ago
Delta
Sat, May 17 - Sat, May 24
PDX
Portland
MDW
Chicago
$223 Roundtrip, found 6 days ago
$223
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, May 17 from Portland to Chicago, returning Sat, May 24, priced at $223 found 6 days ago

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 $179. 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 and Alaska Airlines flight leaving PDX on May 9 2025 and touching down at MDW. The price was last updated on April 22 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 $90. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from PDX on May 31 2025. Prices were last updated on April 22 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.
*Available to One Key members.