Price observed over the last 3 months for a round trip.
Compare all flight tickets and find cheap flights from Portland to Chicago
The cheapest flights right now
Portland – Chicago
Outbound – Dec 3, 2026
direct
4h 2m Return – Dec 9, 2026
direct
4h 43m $297
yesterday
Portland – Chicago
Outbound – Dec 4, 2026
direct
3h 54m Return – Dec 10, 2026
direct
4h 50m $291
yesterday
Portland – Chicago
Outbound – Dec 3, 2026
direct
3h 45m Return – Dec 9, 2026
direct
4h 35m $304
yesterday
Portland – Chicago
Outbound – Dec 6, 2026
direct
3h 54m Return – Dec 12, 2026
direct
4h 52m $338
3 days ago
* Prices are in USD per passenger, including taxes, for a round trip. Prices are based on searches carried out within the last 72 hours. Please note that availability and ticket prices are subject to change and should not be considered as the final price quoted.
Cheapest flight tickets
$260
Average price of a round trip
$349
Average flight ticket price recorded over the last 3 months for a round trip.
Flight duration
4h10
A flight from Portland to Chicago takes on average 4h10.
Best time
June
According to user searches, the ideal month to go to Chicago is June.
The best flight deals for a week
Portland – Chicago
Outbound – Dec 5, 2026
direct
4h 10m Return – Dec 12, 2026
direct
4h 57m $339
3 days ago
Portland – Chicago
Outbound – Dec 6, 2026
direct
3h 54m Return – Dec 12, 2026
direct
4h 52m $338
3 days ago
* Prices are in USD per passenger, including taxes, for a round trip. Prices are based on searches carried out within the last 72 hours. Please note that availability and ticket prices are subject to change and should not be considered as the final price quoted.
Tips for finding a cheap flight from Portland to Chicago
Check out our tips for booking your flight to Chicago (USA) from Portland (USA) at the cheapest possible price.
Usually, the cheapest month to pick up a ticket on this route is August, with an average flight ticket price of $321 (calculation over the last two years). The most touristic season corresponds to the months of October, September and August.
For the cheapest flights, it is advisable to buy your ticket at least 26 days before the departure date.
The airline offering the cheapest flight tickets is American Airlines. A ticket from the airline American Airlines to Chicago costs on average $348.
The airlines that offer the most flights are American Airlines, United Airlines and Southwest Airlines.
Price of flight tickets from Portland to Chicago
Here is some information and tips to know before booking your flight:
- Flight ticket prices range from $260 to $427
- The average price of a flight ticket is about $349
- Prices are lowest for stays in the month of August
- The month in which booking a ticket is cheaper is: October
info departure city :
Portland, USA
airports :
Portland International Airport (PDX)
Pearson Airpark (VUO)
local time :
Portland is a city in the country USA, the time zone is [[timezone]]. In Portland, it is currently {fromLocalTime}, the temperature is on average 18°C, with a minimum of 11°C and a maximum of 26°C.
The city of Portland has 2 airport(s): Portland and Pearson Airpark
destination info :
Chicago, USA
airports :
Chicago-Merrill C. Meigs Field Airport (CGX)
Chicago FSS (CHI)
Chicago-Midway International Airport (MDW)
Chicago-O'Hare International Airport (ORD)
local time :
Chicago is in the country USA, the time zone is [[timezone]]. In Chicago, it is currently {toLocalTime}, the temperature is on average 16°C, with a minimum of 15°C and a maximum of 18°C.
The city of Chicago (CHI) has 4 airport(s): Chicago-Merrill C. Meigs Field, Chicago FSS, Chicago-Midway and Chicago-O'Hare
Useful info about Chicago
What is the least touristic period to go to Chicago?
If you want to visit Chicago during the least touristic period, choose the month of June.
What is the most popular time to travel to Chicago?
In Chicago, the most popular month is October. It is during this period that the prices offered by airlines are also the highest.
When should I book my flight from Portland to Chicago?
According to our data, it is recommended to book your flight 26 days before your departure. If you book your flight ticket 4 weeks before your departure, you may find a price below average. The cheapest day to book a flight from Portland to Chicago is Sunday.
What are the arrival and destination airports when traveling between Portland and Chicago?
When you leave, you can leave from Portland, and you will arrive at Chicago-Midway or Chicago-O'Hare.
How to reach Portland airport from the city centre?
The airport Portland is located 10 km or Pearson Airpark is located 10 km from the city centre. You can access it by using public transportation, taking a taxi, or renting a car.
Are there other means of transportation to go from Portland to Chicago?
Airplane is the only means of transportation listed on Liligo for this journey.
Are there big differences in weather between Portland and Chicago?
In summer, the average temperature is 22°C in Chicago and 20°C in Portland. The average rainfall in summer is 145 mm in Chicago and 19 mm in Portland. In summer, it is warmer in Chicago and it rains less in Portland. In winter, it is colder in Portland and it rains more in Portland.
