Cheap flights from Portland to Chicago from $91
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 8/19. 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 Portland to Chicago Midway Airport
Our best Frontier deals on Portland to Chicago Midway Airport flight tickets
Delta flights from Portland to Chicago Midway Airport
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How to get the cheapest flight ticket from Portland 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 Portland, with most prices found around $253. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Portland during the month August is also very affordable. Most momondo users find prices during this month for around $286.
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 Portland. The lowest ticket price found for a Friday departure recently was $444. 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 Portland because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $542.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Portland 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 $460. 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 Midway flight route?
Fly from Portland to Chicago Midway for the best Portland - Chicago Midway flight prices
What is the cheapest airline that flies from Portland to Chicago Midway?
Southwest, Delta, and Frontier are the most popular carriers operating from Portland 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 Portland according to our data. Southwest is the first choice among our users, with 79% 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 Portland to Chicago Midway Airport on average per day?
As of June 2025, 3 flights take off from Portland and land in Chicago Midway Airport each day. The most common flight departure time for this route is 8:00AM, with 52% of daily flights taking off at noon.
How many flights depart from Portland to Chicago Midway Airport on average per week?
21 flights are operational weekly from Portland to Chicago Midway Airport as of June 2025. The most popular departure day for this route is Mon, with 14% of flights per week taking off on this day.
When to book flights from Portland to Chicago Midway Airport
Cheap Portland to Chicago Midway Airport (PDX to MDW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Portland to Chicago Midway Airport
How far is Portland to Chicago Midway by plane?
Chicago Midway is 1749.8 mi away from Portland. By plane, this route typically takes 3h 50m.
When did momondo last update prices for flights from Portland Airport to Chicago Midway Airport?
Prices for flights from Portland Airport to Chicago Midway Airport were last updated today.
How many operators does momondo search for flights from Portland Airport to Chicago Midway Airport?
The number of operators available for flights from Portland Airport to Chicago Midway Airport is 3 as of June 2025.
How old do you have to be to fly from Portland Airport 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 Portland Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents required for your trip to Chicago Midway 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 Midway 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 Midway Airport?
momondo data reveals that the most frequently booked plane model on the route from Portland to Chicago Midway Airport is Boeing 737 MAX 9, representing 13.62% of all bookings. The subsequent popular models are Boeing 737-800 Passenger/BBJ2 (winglets) at 11.43%, Airbus A321-100/200 at 10.40%, and Boeing 737-800 at 9.98%.
What is the most popular airline from Portland to Chicago Midway Airport?
momondo data reveals that the most frequently booked airline on the route from Portland to Chicago Midway Airport is Southwest, representing 79% of all bookings. The subsequent popular airlines are Frontier at 14% and Delta at 7%.
Best airlines flying from Portland to Chicago Midway Airport
Compare and see reviews for airlines that fly from Portland to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $108 | Free Cancellation | Rating 5.9 3,296 reviews | |||
| PriceFrom $253 | Free Cancellation | Rating 8.0 4,278 reviews |
Southwest Flights From Portland to Chicago Midway Airport
Southwest operates around 21 flights from Portland to Chicago Midway Airport every week. The average price of these flights found in the last 72 hours has been $437, but momondo users have found Southwest deals from Portland to Chicago Midway Airport from as low as $253 round-trip. Southwest has been scored 8.0/10 in 4,278 reviews.
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Why should I use momondo to find a flight deal from Portland to Chicago?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Portland to Chicago. Millions of users trust and use momondo every year so you are in good hands.
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?
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 Portland to Chicago.
I’m not ready to book a flight from Portland to Chicago right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Chicago from Portland. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.