Portland (PDX) → Chicago (ORD)
About Portland to Chicago Flights
Discover the best flights from Portland to Chicago, covering 2,791 km in approximately 3h 59m. Portland (PDX) to Chicago (ORD) is one of the popular medium-haul routes within United States. With 5 major airlines operating this route including direct flights, travelers have plenty of options to choose from. Whether you're traveling for business or leisure, our comprehensive guide helps you find the best deals, understand seasonal price variations, and choose the right airline for your journey from Portland to Chicago.
12-Month Price History
Flight prices from Portland to Chicago vary significantly throughout the year. February typically offers the best deals with average prices around $441, while July sees the highest prices, averaging $731. Savvy travelers can save up to 40% by choosing their travel dates wisely.
Best Time to Fly
Cheapest Month
February
Save up to 40% on average
Most Expensive
July
Peak season pricing
Book in Advance
47 days
For best prices
Booking Tips
For the best prices on Portland to Chicago flights, we recommend booking 43 days in advance. Domestic flights typically see price increases as the departure date approaches, so early booking is advisable. Tuesday and Wednesday departures often offer the lowest fares, while Friday and Sunday flights tend to be more expensive due to business and leisure travel demand. Consider flying early morning or late evening for additional savings, as these off-peak times usually have lower demand.
Airlines Serving This Route
| Airline | Economy | Business | First |
|---|---|---|---|
Alaska Airlines AS | $730 | $2620 | $4660 |
United Airlines UA | $790 | $3110 | $3950 |
SkyWest Airlines OO | $830 | $2970 | $5030 |
Kalitta Air K4 | $870 | $2580 | $4260 |
American Airlines AA | $960 | $3090 | $4670 |
Alaska Airlines
AS
Economy
$730
Business
$2620
First
$4660
United Airlines
UA
Economy
$790
Business
$3110
First
$3950
SkyWest Airlines
OO
Economy
$830
Business
$2970
First
$5030
Kalitta Air
K4
Economy
$870
Business
$2580
First
$4260
American Airlines
AA
Economy
$960
Business
$3090
First
$4670
Prices shown are estimates based on historical data. Actual prices may vary based on dates, availability, and current promotions.
Alternative Flight Options
Portland → Milwaukee
Portland International (PDX) to Milwaukee Mitchell International (MKE)
Distance: 2,757 km
Average price: $514
Portland → Chicago
Portland International (PDX) to Chicago Midway International (MDW)
Distance: 2,811 km
Average price: $522
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Frequently Asked Questions
How long is the flight from Portland to Chicago?
The flight time from Portland (PDX) to Chicago (ORD) is approximately 3 hours and 59 minutes. This duration is for direct flights and may vary depending on aircraft type, weather conditions, and air traffic.
What is the distance between Portland and Chicago?
The aerial distance between Portland and Chicago is 2,791 kilometers (1,734 miles). This is the straight-line distance, which is used to calculate flight times.
Which airlines fly from Portland to Chicago?
Several airlines operate flights between Portland and Chicago, including American Airlines, United Airlines, Alaska Airlines and 2 more airlines. Direct flights are available on this route.
What is the cheapest month to fly from Portland to Chicago?
Based on historical data, February typically offers the lowest airfares for flights from Portland to Chicago. However, prices can vary based on holidays, events, and airline promotions. We recommend checking our price calendar for the most up-to-date information.
How far in advance should I book my flight to Chicago?
For the best prices on Portland to Chicago flights, we recommend booking 69 days in advance. Domestic flights can sometimes offer good last-minute deals, but advance booking is usually cheaper.
Do I need a visa to travel from Portland to Chicago?
Visa requirements depend on your nationality and the purpose of your visit. Since this is a domestic flight, no visa is required for citizens.
What is the time difference between Portland and Chicago?
Portland operates on America/Los_Angeles time zone, while Chicago is in the America/Chicago time zone. For current time differences and to plan your schedule, visit our partner site timezig.com for accurate timezone conversions.