Cheap flights from Oregon to Chicago from $71
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Oregon to Chicago departing on 5/16. 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 Oregon 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 Oregon, 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 Oregon to Chicago during August average around $289.
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 Wednesday when prices can be found for as low as $460. 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 Oregon to Chicago for around $597.
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 Oregon to Chicago during this time can be as low as $356. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $560.
What is the cheapest Oregon to Chicago flight route?
Fly from Portland to Chicago O'Hare Intl for the best Oregon - 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 Oregon when booking 21 weeks ahead of your departure date. In general, you can expect to find flights to Chicago 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 from Oregon for as low as $295 on momondo.
What cabin class options are available on Oregon to Chicago flights?
There are 4 cabin classes available to choose from on Oregon to Chicago 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 Oregon to Chicago?
Spirit Airlines, Southwest, and United Airlines are the most popular carriers operating from Oregon 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 Oregon 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. 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 Oregon to Chicago on average per day?
32 flights are operational daily from Oregon to Chicago as of May 2025. The most popular departure time for this route is 7:00AM, with 62% of flights per day taking off at noon.
How many flights depart from Oregon to Chicago on average per week?
227 flights are operational weekly from Oregon to Chicago as of May 2025. The most popular departure day for this route is Mon, with 15% of flights per week taking off on this day.
Cheap Oregon to Chicago flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Oregon to Chicago
When did momondo last update prices for flights from Oregon to Chicago?
Prices for flights from Oregon to Chicago were last updated today.
How many operators does momondo search for flights from Oregon to Chicago?
As of May 2025, there are 8 operators available to choose from for flights from Oregon to Chicago.
How old do you have to be to fly from Oregon to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Oregon to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Oregon to Chicago?
Based on momondo bookings for flights between Oregon and Chicago, the leading plane model is Boeing 737-800, making up 14.16% of the total bookings. Other popular models include Boeing 737-900 with 13.75%, Boeing 737 MAX 8 with 10.69%, and Airbus A320-100/200 with 10.51%.
Best airlines flying from Oregon to Chicago
Compare and see reviews for airlines that fly from Oregon to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $82 | Free Cancellation | Rating 6.3 7,967 reviews | |||
| PriceFrom $108 | Free Cancellation | Rating 5.9 3,288 reviews | |||
| PriceFrom $123 | Free Cancellation | Rating 8.0 7,941 reviews | |||
| PriceFrom $185 | Free Cancellation | Rating 8.0 9,987 reviews | |||
| PriceFrom $202 | Free Cancellation | Rating 7.9 2,420 reviews | |||
| PriceFrom $211 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $211 | Free Cancellation | Rating 7.4 8,702 reviews | |||
| PriceFrom $249 | Free Cancellation | Rating 8.0 4,292 reviews |
Traveling to a place near Chicago?
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Why should I use momondo to find a flight deal from Oregon to Chicago?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Oregon to Chicago. Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from Oregon to Chicago with flexible booking policies on momondo?
Flights from Oregon 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 Oregon to Chicago?
Once all potential Oregon 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 Oregon 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 Oregon and alert you when they change.