Cheap flights from Portland to Chicago from $85
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Portland to Chicago departing on 7/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Portland to Chicago
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
Hawaiian Airlines flights from Portland to Chicago
Our best Hawaiian Airlines deals on Portland to Chicago flight tickets
United Airlines flights from Portland to Chicago
Our best United Airlines deals on Portland to Chicago flight tickets
See travel insights to Chicago from
How to get the cheapest flight ticket from Portland to Chicago
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 cheapest month to fly to Chicago?
The month of January is, on average, the cheapest month to fly to Chicago from Portland, with most prices found around $263. If you’re not able to fly to Chicago in January, then August is your next best option. Flight prices from Portland to Chicago during August average around $278.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $458. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Portland to Chicago for around $587.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Portland to Chicago during this time can be as low as $311. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $529.
What is the cheapest Portland to Chicago flight route?
Fly from Portland to Chicago O'Hare Intl for the best Portland - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from Portland when booking 21 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $358 when searching 21 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Portland for as low as $304 on momondo.
What cabin class options are available on Portland to Chicago flights?
There are 4 cabin classes available to choose from on Portland to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Portland to Chicago flights?
No. A direct flight is the cheapest option for a flight between Portland to Chicago.
How have Portland to Chicago flight prices changed over time?
As of June 2025, prices for Portland to Chicago flights are approximately 48% cheaper when compared to flights at the same time last year.
What is the cheapest airline that flies from Portland to Chicago?
Spirit Airlines, United Airlines, and Southwest are the most popular carriers operating from Portland to Chicago
What airlines fly to Chicago?
United Airlines, Alaska Airlines and American Airlines are the top three most popular airlines that fly to Chicago from Portland according to our data. United Airlines is the first choice among our users, with 48% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 8 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Portland to Chicago on average per day?
The number of flights available between Portland and Chicago is 26 per day as of June 2025. The most frequent departure time is 7:00AM, with 60% of daily flights leaving at noon.
How many flights depart from Portland to Chicago on average per week?
187 flights are operational weekly from Portland to Chicago as of June 2025. The most popular departure day for this route is Thu, with 18% of flights per week taking off on this day.
When to book flights from Portland to Chicago
Cheap Portland to Chicago (PDX to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Portland to Chicago
How far is Portland to Chicago by plane?
Portland and Chicago are 1753.4 mi apart from one another. A reasonable flight in good conditions will take 3h 50m.
When did momondo last update prices for flights from Portland Airport to Chicago?
Prices for flights from Portland Airport to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from Portland Airport to Chicago?
There are 8 operators available for flights from Portland Airport to Chicago as of June 2025.
How old do you have to be to fly from Portland Airport to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Portland to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Portland to Chicago is Boeing 737 MAX 9 (13.26% of total bookings). The next most popular plane models are Boeing 737-900 (12.84%), Boeing 737-800 (11.75%), and Airbus A320-100/200 (10.90%).
What is the most popular airline from Portland to Chicago?
momondo data reveals that the most frequently booked airline on the route from Portland to Chicago is United Airlines, representing 37% of all bookings. The subsequent popular airlines are Alaska Airlines at 26%, American Airlines at 14%, and Spirit Airlines at 10%.
Best airlines flying from Portland to Chicago
Compare and see reviews for airlines that fly from Portland to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $86 | Free Cancellation | Rating 6.3 8,052 reviews | |||
| PriceFrom $108 | Free Cancellation | Rating 5.9 3,295 reviews | |||
| PriceFrom $123 | Free Cancellation | Rating 8.0 7,946 reviews | |||
| PriceFrom $186 | Free Cancellation | Rating 8.0 10,000 reviews | |||
| PriceFrom $202 | Free Cancellation | Rating 7.8 2,494 reviews | |||
| PriceFrom $217 | Free Cancellation | Rating 7.4 8,790 reviews | |||
| PriceFrom $226 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $253 | Free Cancellation | Rating 8.0 4,287 reviews |
Alaska Airlines Flights From Portland to Chicago
Alaska Airlines flies from Portland to Chicago around 11 times per week, with 10,000 momondo users rating the airline 8.0/10. The cheapest Alaska Airlines deal from Portland to Chicago in the last 72 hours was $186 (round-trip), much lower than the average airfare cost of $337 for Alaska Airlines flights on this route.
Southwest Flights From Portland to Chicago
Another popular option for Portland to Chicago flights is Southwest (8.0/10, 4,287 ratings). Southwest flies from Portland to Chicago around 15 times per week, with deals starting from $253 round-trip and rising to an average price of around $437.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Portland to Chicago?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Portland.
Can I find flights from Portland to Chicago with flexible booking policies on momondo?
Flights from Portland to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Portland to Chicago?
Once all potential Portland to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.
I’m not ready to book a flight from Portland to Chicago right now. Can momondo alert me if prices change?
Yes. momondo can track prices for Portland to Chicago 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.