Flights from Portland, Oregon to Chicago, United States

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Did you mean flights from Chicago to Portland, Oregon?

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.

Non Stop versus Connecting
Advanced PurchaseNon StopConnecting
< 7 days $506 $208
7-14 days $308 $256
14-21 days $255 $236
21-30 days $217 $168
30-60 days $217 $168
60-90 days $255 $158
90+ days $255 $182

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
February Portland, Oregon Chicago Alaska 2/29/20 3/3/20 0 $217
March Portland, Oregon Chicago Alaska 3/3/20 3/7/20 0 $217
April Portland, Oregon Chicago Alaska 4/1/20 4/7/20 0 $217
May Portland, Oregon Chicago Alaska 5/1/20 5/3/20 0 $194
June Portland, Oregon Chicago Alaska 6/10/20 6/21/20 1 $259
July Portland, Oregon Chicago Major Airlines 7/21/20 7/28/20 1 $255
August Portland, Oregon Chicago Major Airlines 8/21/20 8/24/20 1 $255
September Portland, Oregon Chicago Major Airlines 9/10/20 9/14/20 1 $255

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

SunMonTueWedThuFriSat
9 10 11 12 13 14 15
$410
16 17 18 19 20 21 22
$410 $309
23 24 25 26 27 28 29
$309 $217
1 2 3 4 5 6 7
$217 $217
8 9 10 11 12 13 14
$217 $245
15 16 17 18 19 20 21
$245

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 $231.

The average price for direct flights from Portland, Oregon to Chicago is $252.

The chart below shows up to date information regarding non-stop flights from Portland, Oregon to Chicago.

Weekly Direct Flights from Portland, Oregon to Chicago - By Carrier
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
American 2 2 2 2 2 2 2 01:00 10:16
Alaska 2 2 2 2 2 2 2 02:00 13:00
United 4 4 4 4 4 3 4 02:24 18:12
Major Airlines 2 2 2 2 2 2 1 00:50 10:25

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 $94.

The average price for round trip flights from Portland, Oregon to Chicago is $230.

Portland, Oregon to Chicago Flight Questions

Below are some common questions that asked about this flight route:

Question: How long is the flight from Portland, Oregon to Chicago?
Answer: The average Portland, Oregon to Chicago flight time is 3 hours and 59 minutes.
Question: How far is Chicago from Portland, Oregon?
Answer: The distance from Portland, Oregon to Chicago is 1,733 miles (2,788 kilometers).
Question: How common are direct flights from Portland, Oregon to Chicago?
Answer: There are 65 direct flights from Portland, Oregon to Chicago.
Question: What are the most popular Portland, Oregon airlines for direct flights from Portland, Oregon to Chicago?
Answer: United Airlines provides 40% of the non-stop flights between Portland, Oregon and Chicago.

Airlines in Portland, Oregon flying to Chicago Last modified: Jun 2, 2020 5:42 -04:00Number of routes searched: 0Number of itineraries searched: 0

Wondering which airlines fly out of Portland, Oregon to Chicago? We've gathered the average price of Portland, Oregon airlines with flights to Chicago. Different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Portland, Oregon to Chicago Airports

These are the major commercial airports we're currently monitoring in Portland, Oregon and Chicago. If your route includes a city with multiple airports, you may be able to find substantial savings by choosing an alternate airport.

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.

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Cheap Flights from Portland, Oregon to Chicago