Cheap flights from Chicago to Portland from $81
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Portland departing on 5/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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How to get the cheapest flight ticket from Chicago to Portland
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between Chicago and Portland?
What is the cheapest month to fly to Portland?
The cheapest month to fly to Portland from Chicago is in September. Flight prices, which tend to average around $264, are often lower during this time because this is during the off-season. If you don’t want to visit Portland in September, then you should wait until January to fly from Chicago, when ticket prices are also cheap, with an average price of $274.
What is the cheapest day to depart on your flight to Portland?
The cheapest day to depart on your flight to Portland is on a Wednesday when prices can be found for as low as $304. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Portland is Monday, with ticket prices averaging around $384.
What is the cheapest time of day to depart on your flight to Portland?
The cheapest time of day to fly to Portland is in the evening when flights can be purchased for as low as $219. In the afternoon is when there is more demand to fly to Portland, so prices are often more expensive at around $388 per ticket.
What is the cheapest Chicago to Portland flight route?
Fly from Chicago Midway to Portland for the best Chicago - Portland flight prices
How far in advance should I book a flight to Portland?
You are more likely to see cheaper flights to Portland from Chicago when booking 5 weeks ahead of your departure date. In general, you can expect to find flights to Portland for around $329 when searching 5 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Portland from Chicago for as low as $277 on momondo.
What cabin class options are available on Chicago to Portland flights?
There are 4 cabin classes available to choose from on Chicago to Portland flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Chicago to Portland?
Spirit Airlines, Southwest, and United Airlines are the most popular carriers operating from Chicago to Portland
What airlines fly to Portland?
United Airlines, Alaska Airlines and American Airlines are the top three most popular airlines that fly to Portland from Chicago according to our data. United Airlines is the first choice among our users, with 45% of people opting to fly with this airline when traveling to Portland. Keep in mind that there are 8 different airlines that fly to Portland on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago to Portland on average per day?
The number of flights available between Chicago and Portland is 17 per day as of April 2025. The most frequent departure time is 8:00PM, with 44% of daily flights leaving in the evening.
How many flights depart from Chicago to Portland on average per week?
As of April 2025, there are 125 flights per week flying from Chicago to Portland. The most common day of the week flights depart is Thu, with 19% of flights taking off on this day.
When to book flights from Chicago to Portland
Cheap Chicago to Portland (CHI to PDX) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Portland
How far is Chicago to Portland by plane?
A flight from Chicago to Portland will travel around 1753.4 mi. Flights usually cover this in 4h 10m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Chicago to Portland Airport?
Prices for flights from Chicago to Portland Airport refresh daily.
How many operators does momondo search for flights from Chicago to Portland Airport?
As of April 2025, there are 8 operators available to choose from for flights from Chicago to Portland Airport.
How old do you have to be to fly from Chicago to Portland Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Portland Airport.
What documentation or ID do you need to fly to Portland Airport?
The travel and health documents required for your trip to Portland Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Portland Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to Portland?
momondo data reveals that the most frequently booked plane model on the route from Chicago to Portland is Boeing 737-800, representing 22.00% of all bookings. The subsequent popular models are Boeing 737-900 at 15.98%, Boeing 737 MAX 8 at 13.14%, and Boeing 737-900 Passenger/BBJ3 (winglets) at 9.09%.
What is the most popular airline from Chicago to Portland?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Chicago to Portland is United Airlines (40% of total bookings). The next most popular airlines are Alaska Airlines (24%), American Airlines (14%), and Spirit Airlines (13%).
Best airlines flying from Chicago to Portland
Compare and see reviews for airlines that fly from Chicago to Portland with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $81 | Free Cancellation | Rating 6.3 7,926 reviews | |||
| PriceFrom $108 | Free Cancellation | Rating 6.0 3,281 reviews | |||
| PriceFrom $134 | Free Cancellation | Rating 7.9 2,380 reviews | |||
| PriceFrom $176 | Free Cancellation | Rating 8.0 7,916 reviews | |||
| PriceFrom $177 | Free Cancellation | Rating 8.0 9,887 reviews | |||
| PriceFrom $197 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $215 | Free Cancellation | Rating 7.4 8,667 reviews | |||
| PriceFrom $238 | Free Cancellation | Rating 8.0 4,280 reviews |
Alaska Airlines Flights From Chicago to Portland
Alaska Airlines flight deals from Chicago to Portland start from $177 round-trip. Over the 2 Alaska Airlines flights for this route in a normal week, average airfare is usually $287 round-trip - but some users have found much cheaper deals with momondo.
Southwest Flights From Chicago to Portland
Another popular option for Chicago to Portland flights is Southwest (8.0/10, 4,280 ratings). Southwest flies from Chicago to Portland around 10 times per week, with deals starting from $238 round-trip and rising to an average price of around $433.
Traveling to a place near Portland?
Book flights to Portland if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Chicago to Portland?
It is quick and easy to find Chicago to Portland flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Portland that suits you.
Can I find flights from Chicago to Portland with flexible booking policies on momondo?
All flight searches from Chicago to Portland on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from Chicago to Portland?
momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Portland.
I’m not ready to book a flight from Chicago to Portland right now. Can momondo alert me if prices change?
Yes. momondo can track prices for Chicago to Portland flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.