Flights from Chicago to Portland
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From $278 · Prices update daily
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The quick answer
Flights from Chicago to Portland start around $278 round-trip. Airlines on this route include: Alaska Airlines, Frontier Airlines. Cheapest month: July; peak: June (about +30%).
Price calendar — next 60 days
★ Cheapest: $278 on Fri, Jul 31 · F9
Lowest return fares · Prices update daily · Final price confirmed at booking
Price calendar — Chicago to Portland
Month-by-month lowest fares. Green = cheapest dates.
United States essentials
🇺🇸 Domestic flight — no passport required
Domestic flight — no passport required for US citizens. Bring REAL ID for security.
Full Portland visa guide →🆘 Emergency
911
💱 Currency
US Dollar ($)
🕐 Time zone
UTC−5 to −10
🗣️ Language
English
🔌 Plugs
Type A/B · 120V
🚗 Driving
Right side
💡 Tipping
Expected — 15–20% at restaurants
📞 Dial code
+1
Entry rules can change — always confirm with official sources before booking.
Stay connected in Portland
Skip roaming fees — get a local eSIM before you land. Works in 200+ countries and activates instantly, so you’re online the moment you touch down.
Travel insurance
Protect your Chicago to Portland trip against delays, cancellations, and medical emergencies. US travelers can compare plans from top insurers.
Airport transfer in Portland
Pre-book your ride into Portland. Fixed price, meet & greet, and a driver waiting at arrivals — no meter anxiety after a long flight.
Flight delayed or cancelled?
If your Chicago to Portland flight was delayed more than 3 hours or cancelled, you may be entitled to up to €600 in compensation under EU/UK rules — even if you flew a non-EU airline. Free to check, no win no fee.
More resources
Chicago to Portland — frequently asked
How much is a flight from Chicago to Portland?+
Fares start around $278 round-trip, ranging up to about $395 in peak periods. Prices update daily across 800+ airlines.
What is the cheapest month to fly Chicago to Portland?+
July typically has the lowest fares, while June is the most expensive (around +30%).
Are there direct flights from Chicago to Portland?+
This route is usually served by connecting flights. Use the search above to check for any direct options on your dates.
Which airlines fly from Chicago to Portland?+
Carriers on this route include Alaska Airlines, Frontier Airlines. Compare them side by side in the search above.
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