Flights from Chicago to Portland from $309

Compare All CHI to PDX Flights

Prices are per person for one-way travel. Click “Book” to complete your reservation on the partner site.

1 of 1 flight

Airline	Schedule	Stops	Duration	Price
WN WN · 3579	21:50 CHI 13:18 PDX	0 stop(s)	15h 28m	$309 Best	Book →

Airport Information

Key details about departure and arrival airports for this route

PDX

Portland International Airport

City: Portland
Country: US
Type: Large Airport
Elevation: 31 ft

PDX Airport Guide →

Tips for Chicago to Portland Flights

Save money and travel smarter with these route-specific tips

📅 When to Book

Book CHI–PDX flights 6–8 weeks in advance for the best prices. Last-minute fares are typically 40–60% more expensive on this route.

💰 Price Trends

The average fare is $309, but prices as low as $309 are available.

✈ Direct vs Connecting

No direct flights currently listed. Consider flexible dates or nearby airports for better connections.

📍 Flexible Dates

Flying midweek (Tuesday–Thursday) on CHI–PDX is typically 15–30% cheaper. Use our price comparison to spot the best day to fly.

Top Hotels in Portland

Book accommodation at your destination — top-rated stays near PDX airport

Annesley House

Portland, 4.5★

10.0 $180/night

NRMA Portland Bay Holiday Park

Portland, 3★

9.8 Check Price

Lorelei Bed & Breakfast

Portland, 4★

9.5 $103/night

Seascape Accommodation

Portland, 4★

9.5 Check Price

Cape Nelson Lighthouse

Portland, 5★

9.2 $180/night

Victoria Lodge Motor Inn & Apartments

Portland, 4★

9.1 $88/night

Frequently Asked Questions

Everything you need to know about flying CHI to PDX

What is the cheapest flight from Chicago to Portland?

The cheapest flight from Chicago (CHI) to Portland (PDX) currently starts at $309 with WN. Prices are updated regularly and may vary by date and availability.

How many airlines fly from CHI to PDX?

We found 1 airline(s) operating on the CHI–PDX route, including WN.

Are there direct flights from Chicago to Portland?

No direct flights are currently listed on this route. All available options involve at least one stop. Consider flexible dates or nearby airports for better connection options.

What is the average flight price on this route?

The average flight price from Chicago to Portland is approximately $309. Prices range from $309 to $309 depending on airline, time, and class.

How long is the flight from CHI to PDX?

The average flight duration from Chicago to Portland is approximately 15 hours 28 minutes. Direct flights are typically shorter than connecting options.

What is the baggage allowance on CHI–PDX flights?

Baggage allowance varies by airline and fare class. Most economy fares on this route include 1 carry-on (7–8 kg) and 1 checked bag (20–23 kg). Always confirm baggage rules on the airline's site at booking — low-cost carriers may charge for checked bags.