S$208 Cheap Flights from Portland to Chicago

View S$208 flight on Sat, 30 May, 2026Opens 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 S$208 for one-way flights and S$564 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, 30 May - Sat, 6 Jun
PDX
Portland
MDW
Chicago
S$564 Return, found 1 day ago
S$564
Return
found 1 day ago
Select Delta flight, departing Sat, 30 May from Portland to Chicago, returning Sat, 6 Jun, priced at S$564 found 1 day ago
Delta
Sat, 30 May - Sat, 6 Jun
PDX
Portland
MDW
Chicago
S$826 Return, found 1 day ago
S$826
Return
found 1 day ago
Select Delta flight, departing Sat, 30 May from Portland to Chicago, returning Sat, 6 Jun, priced at S$826 found 1 day ago

Frequently asked questions

How much is a flight from Portland Intl. Airport (PDX) to Chicago Airport?
Based on airfares listed within the last 7 days on Expedia for flights departing within the next year, round-trip flights from PDX Airport to Midway Airport start from S$564. Book now to secure the best price for your adventure. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from PDX to Midway Intl. Airport (MDW)?
Most flights can be conveniently cancelled online, but whether you are charged a fee all comes down to your airline. If you do have to cancel your holiday, follow the easy instructions in the Customer Service Portal.
How do I find cheap flights from Portland Airport to Midway Airport that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for PDX Airport to MDW flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Portland Airport to Midway Airport?
The flying distance between Portland Intl. Airport (PDX) and Midway Intl. Airport (MDW) is 2,800 kilometres. Work your way through your travel song playlist or make a start on the latest bestseller and the trip will whiz by.
Which airlines fly direct from Portland Intl. Airport (PDX) to MDW?
Operating 30 flights each month, Southwest Airlines (WN) is a popular choice when flying directly from Portland Airport to Midway Intl. Airport (MDW).
Are Portland Airport to Chicago Airport flight tickets cheaper when they're purchased at the last minute?
Last-minute planners can occasionally find a bargain, with some of the cheapest fares from PDX to Midway Intl. Airport (MDW) arising a few weeks before the departure date. If you'd rather book ahead, Expedia compares and updates the best flight deals regularly — as early as a year in advance in some cases. It does depend on the carrier though, as not all airlines release prices so far in advance.

Travel information

Origin airport
Portland Intl.
Destination airport
Midway Intl.
Return price
S$564
Distance
2794 km
Average flight time
5 hours 55 mins

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