Top Deals for Flights from PDX to ORD: Your Portland to Chicago Guide
Price data is being collected for this route. Check back soon.
Prices by Month
Price History
Tracking the Jul 2, 2026 departure — the cheapest date we found.
Price Behavior: PDX → ORD
Based on 6 months of fare data collected by Trip Manta.
Lowest Fare
$0
Highest Fare
$258
Median Fare
$181
Price Spread
$258
Prices stay relatively stable on this route.
Cheapest month to fly: July 2026 (from $0)
Most expensive month: April 2026 (from $258)
Biggest price drop caught: $76 between consecutive checks
Most frequent cheapest airline: American
What This Means for You
Flights from Portland to Chicago range from $0 to $258, a $258 spread across the months we track. If your dates are flexible, July 2026 tends to have the lowest fares. Prices are relatively stable on this route, so you may not need to wait long for a good deal. Tracking still helps you confirm you are getting a fair price. We have caught drops as large as $76 between hourly checks on this route.
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From
Portland (PDX)
To
Chicago (ORD)
Airport Information
Portland (PDX)
Portland International Airport (PDX) is consistently ranked as one of the best airports in the United States, largely due to its friendly staff, local shops, and tax-free retail options. Located just 12 miles from the downtown core, it offers a stress-free environment featuring free Wi-Fi and live music performances, ensuring your flight to Chicago starts on a relaxing note.
Chicago (ORD)
Chicago O'Hare International Airport (ORD) is one of the world's busiest aviation hubs, serving as a primary gateway to the American Midwest with non-stop service to hundreds of domestic and international destinations. It features an incredible array of dining options, from gourmet popcorn to high-end steakhouses, and its layout includes an efficient automated people mover system to help passengers navigate between its four sprawling terminals.
Frequently Asked Questions
How long is the flight from PDX to ORD?
A direct flight typically takes between 3 hours and 50 minutes and 4 hours and 15 minutes, covering a distance of approximately 1,750 miles.
Which airlines offer non-stop service from Portland to Chicago?
Major carriers including Alaska Airlines, United Airlines, and American Airlines provide daily non-stop service between Portland International and Chicago O'Hare.
What is the time difference between Portland and Chicago?
Chicago is located in the Central Time Zone, which is exactly two hours ahead of Portland's Pacific Time Zone.
What is the best way to get from O'Hare to downtown Chicago?
The CTA Blue Line 'L' train is the most cost-effective and time-efficient method for reaching the city center, though taxis and rideshares are readily available for those with heavy luggage.
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