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Flights from Portland, Oregon to Chicago, United States
Portland, Oregon to Chicago Last modified: Sep 19, 2023 11:19 -04:00
We've scanned 109,155,000 round trip itineraries and found the cheapest flights to Chicago. Multiple Airlines & Alaska frequently offer the best deals to Chicago flights, or select your preferred carrier below to see the cheapest days to fly.
Where To Buy Cheap Flights from Portland, Oregon to Chicago?
The best way to find a great deal on airfare is to search multiple sites. When you run a search on FareCompare, we search multiple sites and fare sources all at once so you don't have to - which is why we think FareCompare is the best place to find cheap tickets. Airlines can adjust prices for tickets from Portland, Oregon to Chicago based on the day and time that you decide to book your flight. We have collected data from all airlines, and have found that Tuesdays, Wednesdays, and Saturdays are often the best days to book flights. If you'd like to learn more, read our article about the best time to buy airline tickets.
How far in advance should I book tickets from Portland, Oregon to Chicago?
The chart below shows up-to-date information regarding how far in advance to book your flight from Portland, Oregon to Chicago.
| Advanced Purchase | Non Stop | Connecting |
|---|---|---|
| < 7 days | $121 | $168 |
| 7-14 days | $344 | $168 |
| 14-21 days | $218 | $168 |
| 21-30 days | $198 | $168 |
| 30-60 days | $158 | $168 |
| 60-90 days | $158 | $203 |
| 90+ days | $158 | $208 |
Cheapest Day To Fly from Portland, Oregon to Chicago
We've examined 215,181,508 itinerary searches that we've seen for departures in the next 90 days and found that the cheapest day to fly from Portland, Oregon to Chicago is Wednesday. See the chart below to compare prices for other days of the week.
Compare Flight Prices from Portland, Oregon to Chicago by Month
Low priced flights are most commonly available by purchasing between one and three months in advance. International or holiday flights may need to be purchased even further in advance. The chart below shows the cheapest flight prices by month for Portland, Oregon to Chicago flights.
| Month | Origin | Destination | Carrier | Depart Date | Return Date | Stops | Price |
|---|---|---|---|---|---|---|---|
| September | Portland, Oregon | Chicago | Multiple Airlines | 9/27/23 | 9/30/23 | 0 | $121 |
| October | Portland, Oregon | Chicago | Alaska | 10/28/23 | 10/31/23 | 0 | $158 |
| November | Portland, Oregon | Chicago | Frontier | 11/1/23 | 11/5/23 | 1 | $168 |
| December | Portland, Oregon | Chicago | Alaska | 12/24/23 | 1/4/24 | 0 | $158 |
| January | Portland, Oregon | Chicago | Alaska | 1/3/24 | 1/5/24 | 0 | $158 |
| February | Portland, Oregon | Chicago | Frontier | 2/3/24 | 2/8/24 | 1 | $260 |
| March | Portland, Oregon | Chicago | Frontier | 3/2/24 | 3/5/24 | 1 | $268 |
| April | Portland, Oregon | Chicago | Alaska | 4/2/24 | 4/6/24 | 1 | $337 |
Cheap Last Minute Flights from Portland, Oregon to Chicago
Looking for cheap last minute flights or a weekend getaway? We've got you covered with weekend flight deals from Portland, Oregon to Chicago. The chart below shows the best last minute deals and cheap flights this weekend we could find.
Next 30 Days
| Sun | Mon | Tue | Wed | Thu | Fri | Sat |
| 24 | 25 | 26 | 27 | 28 | 29 | 30 |
| $174 | ||||||
| 1 | 2 | 3 | 4 | 5 | 6 | 7 |
| $174 | $177 | |||||
| 8 | 9 | 10 | 11 | 12 | 13 | 14 |
| $177 | $168 | |||||
| 15 | 16 | 17 | 18 | 19 | 20 | 21 |
| $168 | $168 | |||||
| 22 | 23 | 24 | 25 | 26 | 27 | 28 |
| $168 | $158 | |||||
| 29 | 30 | 31 | 1 | 2 | 3 | 4 |
| $158 | ||||||
Connecting Flights vs Direct Flights from Portland, Oregon to Chicago
Flights between some cities may be significantly cheaper if you choose a multi-stop airline ticket. Although these connecting flights sacrifice some convenience, on average, travelers save 20%-60% when they choose to fly multi-stop versus a direct flight.
The average price for connecting flights from Portland, Oregon to Chicago is $269.
The average price for direct flights from Portland, Oregon to Chicago is $214.
The chart below shows up to date information regarding non-stop flights from Portland, Oregon to Chicago.
| Carrier | Mon | Tue | Wed | Thu | Fri | Sat | Sun | Earliest Flight | Latest Flight |
| American | 2 | 2 | 2 | 2 | 2 | 2 | 2 | 01:40 | 09:00 |
| United | 4 | 4 | 4 | 4 | 4 | 4 | 4 | 02:11 | 18:30 |
One Way Flights vs Round Trip Flights from Portland, Oregon to Chicago
We have found that there is often no price difference between buying a round trip flight versus a one way flight. Increased flexibility is the main benefit when it comes to buying a one way flight from Portland, Oregon to Chicago. However, booking a round trip flight can be a simpler process. You can compare round trip and one way flights by using our flight comparison.
The average price for one way flights from Portland, Oregon to Chicago is $117.
The average price for round trip flights from Portland, Oregon to Chicago is $252.
Portland, Oregon to Chicago Flight Questions
Below are some common questions that asked about this flight route:
Farecompare Research Tools
FareCompare's Flight Schedule Search Tool helps you find information about airline schedule filings, including flight numbers, depart times, and travel distance.
Cheap Domestic Flights from Portland - PDX Last modified: Sep 27, 2023 10:06 -04:00
Cheap Domestic Flights to Chicago - CHI Last modified: Sep 27, 2023 10:06 -04:00
