Cheap flights from Portland to Chicago from $69
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 5/29. 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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Delta flights from Portland to Chicago O'Hare Intl Airport
Our best Delta deals on Portland to Chicago O'Hare Intl Airport flight tickets
Spirit Airlines flights from Portland to Chicago O'Hare Intl Airport
Our best Spirit Airlines deals on Portland to Chicago O'Hare Intl Airport flight tickets
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How to get the cheapest flight ticket from Portland to Chicago O'Hare Intl Airport
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 O'Hare Intl Airport?
The month of January is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Portland averaging around $287.
What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?
The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Wednesday when prices can be found for as low as $471. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Portland because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $624.
What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?
Flying to Chicago O'Hare Intl Airport from Portland in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $361 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $578. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Portland to Chicago O'Hare Intl flight route?
Fly from Portland to Chicago O'Hare Intl for the best Portland - Chicago O'Hare Intl flight prices
How far in advance should I book a flight to Chicago O'Hare Intl Airport?
You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Portland when booking 21 weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $354 when searching 21 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Portland for as low as $295 on momondo.
What cabin class options are available on Portland to Chicago O'Hare Intl flights?
There are 4 cabin classes available to choose from on Portland to Chicago O'Hare Intl 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 Portland to Chicago O'Hare Intl?
Spirit Airlines, Alaska Airlines, and Southwest are the most popular carriers operating from Portland to Chicago O'Hare Intl
What airlines fly to Chicago O'Hare Intl Airport?
United Airlines, Alaska Airlines and American Airlines are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Portland according to our data. United Airlines is the first choice among our users, with 46% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 7 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from Portland to Chicago O'Hare Intl Airport on average per day?
As of April 2025, 12 flights take off from Portland and land in Chicago O'Hare Intl Airport each day. The most common flight departure time for this route is 7:00AM, with 53% of daily flights taking off at noon.
How many flights depart from Portland to Chicago O'Hare Intl Airport on average per week?
As of April 2025, there are 88 flights per week flying from Portland to Chicago O'Hare Intl Airport. The most common day of the week flights depart is Tue, with 27% of flights taking off on this day.
When to book flights from Portland to Chicago O'Hare Intl Airport
Cheap Portland to Chicago O'Hare Intl Airport (PDX to ORD) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Portland to Chicago O'Hare Intl Airport
How far is Portland to Chicago O'Hare Intl by plane?
Portland and Chicago O'Hare Intl are 1737.6 mi apart from one another. Flights usually cover this in 3h 56m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Portland Airport to Chicago O'Hare Intl Airport?
Prices for flights from Portland Airport to Chicago O'Hare Intl Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Portland Airport to Chicago O'Hare Intl Airport?
As of April 2025, there are 7 operators available to choose from for flights from Portland Airport to Chicago O'Hare Intl Airport.
How old do you have to be to fly from Portland Airport to Chicago O'Hare Intl Airport?
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 O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The travel and health documents required for your trip to Chicago O'Hare Intl 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 Chicago O'Hare Intl 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 Portland to Chicago O'Hare Intl Airport?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Portland to Chicago O'Hare Intl Airport is Boeing 737-800 (14.98% of total bookings). The next most popular plane models are Boeing 737-900 (14.18%), Boeing 737 MAX 8 (11.35%), and Airbus A320-100/200 (10.59%).
What is the most popular airline from Portland to Chicago O'Hare Intl Airport?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Portland to Chicago O'Hare Intl Airport is United Airlines (45% of total bookings). The next most popular airlines are Alaska Airlines (27%), American Airlines (13%), and Spirit Airlines (12%).
Best airlines flying from Portland to Chicago O'Hare Intl Airport
Compare and see reviews for airlines that fly from Portland to Chicago O'Hare Intl Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $82 | Free Cancellation | Rating 6.3 7,956 reviews | |||
| PriceFrom $108 | Free Cancellation | Rating 5.9 3,284 reviews | |||
| PriceFrom $123 | Free Cancellation | Rating 8.0 7,929 reviews | |||
| PriceFrom $185 | Free Cancellation | Rating 8.0 9,961 reviews | |||
| PriceFrom $201 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $202 | Free Cancellation | Rating 7.9 2,405 reviews | |||
| PriceFrom $214 | Free Cancellation | Rating 7.4 8,696 reviews |
Alaska Airlines Flights From Portland to Chicago O'Hare Intl Airport
Across 3 Alaska Airlines flights from Portland to Chicago O'Hare Intl Airport this week, the average price was $340, with the best Alaska Airlines deals starting from $185 round-trip. 9,961 users have rated Alaska Airlines on momondo, with an average score of 8.0/10.
Hawaiian Airlines Flights From Portland to Chicago O'Hare Intl Airport
The best Hawaiian Airlines deal for Portland to Chicago O'Hare Intl Airport flight tickets found on momondo in the last 72 hours was $202, round-trip. It should be noted that an average Hawaiian Airlines flight deal for this route in this time was higher, at $362 round-trip. Hawaiian Airlines operates 7 flights out of Portland into Chicago O'Hare Intl Airport in an average week, so prices vary by time and availability. 2,405 Hawaiian Airlines reviews by users on momondo have scored the airline at 7.9/10.
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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?
Yes. momondo allows you to filter the results for Portland to Chicago flights to just show those with flexible booking policies.
How can momondo help me find flights from Portland to Chicago?
momondo provides multiple filters to help you find the best flight to Chicago from Portland. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Portland to Chicago right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Portland and alert you when they change.