S$141 Cheap Flights from Portland to Chicago

View S$141 flight on Sat, 28 Feb, 2026Opens in a new window

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

  • notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
  • deals illustration

    Book smarter

    Save up to 40% on select hotels after you book a flight*
  • trophy illustration

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Cheap Flights from Portland to Chicago (PDX-MDW)

Prices were available within the past 7 days and start at S$141 for one-way flights and S$433 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sat, 28 Feb - Sat, 7 Mar
PDX
Portland
MDW
Chicago
S$433 Return, found 2 days ago
S$433
Return
found 2 days ago
Select Delta flight, departing Sat, 28 Feb from Portland to Chicago, returning Sat, 7 Mar, priced at S$433 found 2 days ago
Delta
Sat, 28 Feb - Sat, 7 Mar
PDX
Portland
MDW
Chicago
S$548 Return, found 2 days ago
S$548
Return
found 2 days ago
Select Delta flight, departing Sat, 28 Feb from Portland to Chicago, returning Sat, 7 Mar, priced at S$548 found 2 days ago

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

September is typically the cheapest month to fly

From S$169 - S$497 per traveller.

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$433. 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$433
Distance
2794 km
Average flight time
3 hours 55 mins

Book with confidence

Perfect flights from Portland to Chicago

Your Journey from Portland to Chicago

Start your unforgettable journey with Expedia. Our broad selection of flights from Portland to Chicago caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta. Our selection of flights from Portland Intl. to Midway Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 4 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Portland to Chicago Flights

Experience the joy of finding cheap flights from Portland Intl. to Midway Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$141 and roundtrip prices from S$433*.
 

Pre-Flight Essentials

Ensure a smooth journey from Portland to Chicago with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Chicago

Picture yourself stepping off the plane in Chicago and immersing yourself in the unique atmosphere of . From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Portland to Chicago Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Portland to Chicago.
 

Beyond the Flight – Exploring Chicago

With Expedia, your adventure extends beyond the flight. Explore Chicago at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Portland to Chicago with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Portland to Chicago with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.
Perfect flights from Portland to Chicago

Explore a world of travel with Expedia

*Available to Expedia members.