Top Deals for Flights from PDX to ORD: Your Portland to Chicago Guide
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$102.4
Last updated Feb 16, 2026
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Tracking the Apr 2, 2026 departure — the cheapest date we found.
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Portland (PDX)
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Chicago (ORD)
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Search FlightsTraveling from the lush, green landscapes of the Pacific Northwest to the towering, iconic skyline of the Midwest has never been easier, with numerous non-stop flights connecting Portland International Airport (PDX) and Chicago O'Hare (ORD) multiple times every single day. Whether you are flying for high-stakes business meetings in the Loop or seeking a fun-filled weekend of deep-dish pizza and world-class museums, this four-hour journey bridges two of America's most culturally distinct and vibrant cities. This specific route serves as a vital aerial corridor for travelers wanting to swap the scenic beauty of the Columbia River Gorge for the stunning architectural views along the Chicago River and the vast horizon of Lake Michigan.
Travel Tips
Since the route from PDX to ORD is a highly popular business corridor, booking your flight at least four weeks in advance can save you significant money on premium cabin upgrades or preferred seating. Chicago O'Hare is a massive hub with multiple terminals, so it is highly recommended to download your airline's mobile app to receive real-time gate change notifications, which occur frequently during peak travel hours. Consider using the CTA Blue Line train for an affordable and reliable five-dollar transit option from O'Hare directly into downtown Chicago, effectively bypassing the notorious traffic on the Kennedy Expressway. Finally, remember to pack versatile layers regardless of the season, as Portland's mild humidity and Chicago's famous 'Windy City' lakefront breezes can result in very different temperature perceptions immediately upon landing.
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.
Seasonal Pricing Patterns
Flight prices from Portland to Chicago fluctuate significantly throughout the year based on seasonal demand, with the lowest fares typically appearing during the cold winter months of January and February when tourism levels drop. Conversely, prices peak during the summer festival season in July and August, as well as during major holidays. Booking mid-week, specifically on Tuesdays or Wednesdays, remains the most reliable strategy for securing a budget-friendly seat on this transcontinental route.
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.