Cheap flights from Oregon to Chicago from $78
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 8/14. 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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Frontier flights from Oregon to Chicago Midway Airport
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Southwest flights from Oregon to Chicago Midway Airport
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How to get the cheapest flight ticket from Oregon to Chicago Midway 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 Midway Airport?
The month of February is, on average, the cheapest month to fly to Chicago Midway Airport from Oregon, with most prices found around $253. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Oregon during the month September is also very affordable. Most momondo users find prices during this month for around $289.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Oregon. The lowest ticket price found for a Friday departure recently was $438. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Oregon because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $576.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Oregon in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $289 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $465. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Oregon to Chicago Midway flight route?
Fly from Portland to Chicago Midway for the best Oregon - Chicago Midway flight prices
How far in advance should I book a flight to Chicago Midway Airport?
You are more likely to see cheaper flights to Chicago Midway Airport from Oregon when booking 6 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $401 when searching 6 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Oregon for as low as $240 on momondo.
What cabin class options are available on Oregon to Chicago Midway flights?
There are 1 cabin classes available to choose from on Oregon to Chicago Midway 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 Midway?
Southwest, Delta, and Frontier are the most popular carriers operating from Oregon to Chicago Midway
What airlines fly to Chicago Midway Airport?
Southwest, Frontier and Delta are the top three most popular airlines that fly to Chicago Midway Airport from Oregon according to our data. Southwest is the first choice among our users, with 80% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 3 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from Oregon to Chicago Midway Airport on average per day?
1 flights are operational daily from Oregon to Chicago Midway Airport as of May 2025. The most popular departure time for this route is 6:00AM, with 57% of flights per day taking off at noon.
How many flights depart from Oregon to Chicago Midway Airport on average per week?
The number of flights available between Oregon and Chicago Midway Airport is 8 per week as of May 2025. The most frequent departure day is Mon, with 25% of weekly flights leaving on this day.
Cheap Oregon to Chicago Midway Airport flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Oregon to Chicago Midway Airport
When did momondo last update prices for flights from Oregon to Chicago Midway Airport?
Prices for flights from Oregon to Chicago Midway Airport refresh daily.
How many operators does momondo search for flights from Oregon to Chicago Midway Airport?
As of May 2025, there are 3 operators available to choose from for flights from Oregon to Chicago Midway Airport.
How old do you have to be to fly from Oregon to Chicago Midway 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 Oregon to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Oregon to Chicago Midway Airport?
momondo data reveals that the most frequently booked plane model on the route from Oregon to Chicago Midway Airport is Boeing 737-800 Passenger/BBJ2 (winglets), representing 13.42% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 12.68%, Boeing 737-900 at 12.05%, and Boeing 737-800 at 11.73%.
Best airlines flying from Oregon to Chicago Midway Airport
Compare and see reviews for airlines that fly from Oregon to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $108 | Free Cancellation | Rating 5.9 3,287 reviews | |||
| PriceFrom $215 | Free Cancellation | Rating 8.0 7,934 reviews | |||
| PriceFrom $249 | Free Cancellation | Rating 8.0 4,294 reviews |
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Why should I use momondo to find a flight deal from Oregon to Chicago?
We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Oregon to Chicago for you.
Can I find flights from Oregon to Chicago with flexible booking policies on momondo?
Yes. All flights to Chicago from Oregon on momondo can be compared and filtered by various policies on offer, including flexible booking.
How can momondo help me find flights from Oregon to Chicago?
Once you have performed a search for Oregon to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.
I’m not ready to book a flight from Oregon to Chicago right now. Can momondo alert me if prices change?
Yes. momondo can track prices for Oregon 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.