Price observed over the last 3 months for a round trip.
Compare all flight tickets and find cheap flights from Chicago to Portland
The cheapest flights right now
Chicago – Portland
Outbound – Dec 4, 2026
direct
4h 57m Return – Dec 10, 2026
direct
4h 10m $292
yesterday
Chicago – Portland
Outbound – Dec 5, 2026
direct
4h 50m Return – Dec 11, 2026
direct
3h 54m $291
yesterday
Chicago – Portland
Outbound – Dec 5, 2026
direct
4h 52m Return – Dec 13, 2026
direct
3h 54m $337
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
$261
Average price of a round trip
$392
Average flight ticket price recorded over the last 3 months for a round trip.
Flight duration
4h34
A flight from Chicago to Portland takes on average 4h34.
Best time
October
According to user searches, the ideal month to go to Portland is October.
The best flight deals for a week
Chicago – Portland
Outbound – Dec 5, 2026
direct
4h 52m Return – Dec 13, 2026
direct
3h 54m $337
3 days ago
Chicago – Portland
Outbound – Dec 5, 2026
direct
4h 57m Return – Dec 12, 2026
direct
4h 10m $341
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 Chicago to Portland
Check out our tips for booking your flight to Portland (USA) from Chicago (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 $121 (calculation over the last two years). The most touristic season corresponds to the months of October, June and June.
For the cheapest flights, it is advisable to buy your ticket at least 22 days before the departure date.
The airline offering the cheapest flight tickets is United Airlines. A ticket from the airline United Airlines to Portland costs on average $366.
The airlines that offer the most flights are American Airlines, Alaska Airlines and United Airlines.
Price of flight tickets from Chicago to Portland
Here is some information and tips to know before booking your flight:
- Flight ticket prices range from $261 to $498
- The average price of a flight ticket is about $392
- Prices are lowest for stays in the month of August
- The month in which booking a ticket is cheaper is: October
info departure city :
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 a city in the country USA, the time zone is [[timezone]]. In Chicago, it is currently {fromLocalTime}, 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
destination info :
Portland, USA
airports :
Portland International Airport (PDX)
Pearson Airpark (VUO)
local time :
Portland is in the country USA, the time zone is [[timezone]]. In Portland, it is currently {toLocalTime}, 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
Useful info about Portland
What is the least touristic period to go to Portland?
If you want to visit Portland during the least touristic period, choose the month of October.
What is the most popular time to travel to Portland?
In Portland, 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 Chicago to Portland?
According to our data, it is recommended to book your flight 22 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 Chicago to Portland is Saturday.
What are the arrival and destination airports when traveling between Chicago and Portland?
When you leave, you can leave from Chicago-Midway or Chicago-O'Hare, and you will arrive at Portland.
How to reach Chicago airport from the city centre?
The airport Chicago-Merrill C. Meigs Field is located 4 km, Chicago FSS is located 29 km, Chicago-Midway is located 12 km or Chicago-O'Hare is located 29 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 Chicago to Portland?
Airplane is the only means of transportation listed on Liligo for this journey.
Are there big differences in weather between Chicago and Portland?
In summer, the average temperature is 20°C in Portland and 22°C in Chicago. The average rainfall in summer is 19 mm in Portland and 145 mm in Chicago. 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.
