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Cheap Flights from Portland to Chicago, IL, United States - PDX to CHI

Popular flights from Portland to Chicago

If your flight days are flexible and you looking for a good deal, our charts on cheap flights provide some insight regarding affordable flight options for your next big adventure.

Alaska Airlines
Departure Date Return Date Lowest Price
Mar 15, 2016 Mar 22, 2016 $224
American Airlines
Departure Date Return Date Lowest Price
May 4, 2016 May 11, 2016 $177
May 18, 2016 May 24, 2016 $177
Frontier Airlines
Departure Date Return Date Lowest Price
May 7, 2016 May 11, 2016 $199
JetBlue Airways
Departure Date Return Date Lowest Price
May 31, 2016 Jun 5, 2016 $763
Spirit Airlines
Departure Date Return Date Lowest Price
May 14, 2016 May 23, 2016 $161
United Airlines
Departure Date Return Date Lowest Price
May 4, 2016 May 11, 2016 $210
Virgin America
Departure Date Return Date Lowest Price
May 16, 2016 May 19, 2016 $339

How Much Does it Cost to Fly from Portland to Chicago (PDX to CHI)?

We have collected flight cost data from across the web for travel from Portland to Chicago, and have found the average flight price for this trip to be $179.

When Can I Buy the Cheapest Flight from Portland to Chicago (PDX to CHI)?

Airlines can adjust prices for plane tickets from Portland to Chicago based on the day and time that you decide to book your flight. We have collected data from all airlines, and have discovered that the best days to book flights are Tuesdays, Wednesdays, and Saturdays. Read our article to find more information about the best time to buy airline tickets.

How far in advance should you book flights from Portland to Chicago

The chart below shows up-to-date information regarding how far in advance a flight from Portland to Chicago should be booked.

Non Stop versus 1-Stop
Advanced PurchaseNon StopOne Stop
< 7 days $353 $357
7-14 days $271 $279
14-21 days $233 $237
21-30 days $233 $237
30-60 days $224 $226
60-90 days $177 $210
90+ days $161 $226

Cheapest Day To Fly from Portland to Chicago

The chart below shows up-to-date information regarding the cheapest days to fly from Portland to Chicago.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$180 $180 $177 $180 $179 $179 $179

Lowest Fares Chart By Month from Portland to Chicago

The chart below shows the lowest fare by month when flying from Portland to Chicago.

Month Origin Destination Carrier Depart Date Return Date Stops Price
February Portland Chicago American 2/27/16 3/5/16 0 $271
March Portland Chicago Alaska 3/15/16 3/22/16 0 $224
April Portland Chicago Spirit 4/15/16 4/17/16 0 $179
May Portland Chicago Spirit 5/14/16 5/23/16 0 $161
June Portland Chicago Spirit 6/1/16 6/7/16 0 $187
July Portland Chicago Frontier 7/23/16 7/30/16 0 $208
August Portland Chicago Spirit 8/23/16 8/30/16 0 $187
September Portland Chicago Spirit 9/16/16 9/19/16 0 $179

Cheapest Weekend Non-Stop Flights for the Next 30 Days from Portland to Chicago

If you're ready to take a trip in the next 30 days and want to fly on the weekend, you might be wondering which weekend is the cheapest to fly. The chart below shows up-to-date data regarding weekend flight prices from Portland to Chicago.

Next 30 Days

SunMonTueWedThuFriSat
14 15 16 17 18 19 20
$353
21 22 23 24 25 26 27
$353 $338
28 29 1 2 3 4 5
$338 $233
6 7 8 9 10 11 12
$233 $271
13 14 15 16 17 18 19
$271 $461
20 21 22 23 24 25 26
$461

TIPSave $76 by flying into Milwaukee instead of Chicago from Portland

Non-Stop vs Connecting Flights from Portland to Chicago (PDX to CHI)

Your Portland to Chicago flight can be significantly cheaper by choosing 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 to Chicago is $259.

The average price for non-stop flights from Portland to Chicago is $213.

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

Nonstop Flight Details from Portland to Chicago
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
American 1 1 1 1 1 1 1 05:00 05:00
Alaska 1 1 1 1 1 1 1 10:30 10:30
United 2 2 2 2 2 1 2 06:05 23:15

Round Trip vs One Way Flights from Portland to Chicago (PDX to CHI)

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 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 to Chicago is $128.

The average price for round trip flights from Portland to Chicago is $238.

Portland to Chicago Flight Questions

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

Question: How long is a direct flight from Portland to Chicago?
Answer: The average Portland to Chicago flight time is 3 hours and 56 minutes.
Question: How many miles are there between Portland and Chicago?
Answer: The distance from Portland to Chicago is 1733 miles.
Question: How common are direct flights from Portland to Chicago?
Answer: There are 27 direct flights from Portland to Chicago.
Question: What is the most popular airline for non-stop flights from Portland to Chicago?
Answer: United Airlines provides 48% of the non-stop flights between Portland and Chicago.
Question: What are the most popular connecting cities when flying from Portland to Chicago?
Answer: Atlanta, GA

Airlines Flying from Portland to Chicago (PDX to CHI)

Below are the different airlines that fly from Portland to Chicago with the average price of their plane tickets. Just remember that different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Below is the full flight schedule summary of the next 30 days for flights from Portland to Chicago.

Portland to Chicago
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American - X X X X X X X
American DFW X X X X X X X
Alaska - X X X X X X X
Alaska SEA X X X X X X X
Delta ATL X X X X X X X
Spirit LAS X X X X X X X
United - X X X X X X X
United SFO X X X X X X X
Virgin America SFO X X X X X X X
Southwest - X X X X X X X
Southwest SMF X X X X X X X

Airports for Your Route

These pages contain information about the major airports in Portland and Chicago, so you can feel comfortable knowing how to get around whether you are about to take off or you just landed.

Cheap Domestic Flights from Portland - PDX

FlightsAirlineLowest Price
Portland to New York American, Alaska, JetBlue, Frontier, Spirit, Sun Country, United, Virgin America $272
Portland to Milwaukee American, Alaska, Frontier, United $242
Portland to Atlanta American, Alaska, Frontier, Spirit, United $258
Portland to Dallas - Ft Worth American, Alaska, Frontier, Spirit, United, Virgin America $177
Portland to Detroit American, Alaska, JetBlue, Frontier, Spirit, United $244
Portland to South Bend Alaska, United $402
Portland to Madison American, Alaska, Frontier, United $404
Portland to Minneapolis - St Paul American, Alaska, Frontier, Spirit, Sun Country, United $234
Portland to Indianapolis American, Alaska, Frontier, United $234

Cheap Domestic Flights to Chicago - CHI

FlightsAirlineLowest Price
Seattle to Chicago American, Alaska, JetBlue, Frontier, Spirit, United, Virgin America $189
Eugene to Chicago American, Alaska, United $302
Pasco to Chicago American, Alaska, United $314
Redmond to Chicago American, Alaska, United $371
Wenatchee to Chicago American, Alaska $490
Yakima to Chicago American, Alaska $394
North Bend to Chicago United Check Dates
Seattle to Atlanta American, Alaska, Frontier, Spirit, United $266
Seattle to Milwaukee American, Alaska, Frontier, United $258
Seattle to New York American, Alaska, JetBlue, Frontier, Sun Country, United, Virgin America $237
Seattle to Dallas - Ft Worth American, Alaska, Frontier, Spirit, Sun Country, United, Virgin America $196
Seattle to Detroit American, Alaska, JetBlue, Spirit, United $277
Seattle to Minneapolis - St Paul American, Alaska, Frontier, Sun Country, United $237
Seattle to Indianapolis American, Alaska, Frontier, United $241
Seattle to Madison American, Alaska, Frontier, United $432
Seattle to South Bend American, United $352
Seattle to St Louis American, Alaska, Frontier, United $242
Seattle to Grand Rapids American, Alaska, United $348
Seattle to Washington American, Alaska, JetBlue, Frontier, Sun Country, United, Virgin America $242
Seattle to Los Angeles American, Alaska, Spirit, United, Virgin America $86
Seattle to Cincinnati American, Alaska, Frontier, United $277
Cheap Flights from Portland to Chicago, IL, United States, from $161 Round trip from PDX to CHI