Flights from Portland to Chicago from $158

PDX

Portland

One-way

CHI

Chicago

Flights from

$158

Compare 1 options across 1 airline

Updated 1 month ago

$158

Cheapest Flight

$158

Average Price

Direct Flights

Airlines

Looking for the return flight? Chicago to Portland from $309

CHI → PDX Flights

Compare All PDX to CHI 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
F9 F9 · 1106	Schedule on partner site	1 stop(s)	—	$158 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 Portland to Chicago Flights

Save money and travel smarter with these route-specific tips

📅 When to Book

Book PDX–CHI 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 $158, but prices as low as $158 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 PDX–CHI is typically 15–30% cheaper. Use our price comparison to spot the best day to fly.

Frequently Asked Questions

Everything you need to know about flying PDX to CHI

What is the cheapest flight from Portland to Chicago?

The cheapest flight from Portland (PDX) to Chicago (CHI) currently starts at $158 with F9. Prices are updated regularly and may vary by date and availability.

How many airlines fly from PDX to CHI?

We found 1 airline(s) operating on the PDX–CHI route, including F9.

Are there direct flights from Portland to Chicago?

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 Portland to Chicago is approximately $158. Prices range from $158 to $158 depending on airline, time, and class.

What is the baggage allowance on PDX–CHI 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.

From $158

Book Cheapest →