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

Popular flights from Portland to Chicago

We’ve got the inside scoop on finding the best time to fly for the best price. Not sure when to travel for your next vacation? Find details below on when-to-fly and when-to-buy.

Alaska Airlines
Departure Date Return Date Lowest Price
May 7, 2016 May 11, 2016 $280
American Airlines
Departure Date Return Date Lowest Price
May 14, 2016 May 21, 2016 $283
Frontier Airlines
Departure Date Return Date Lowest Price
May 14, 2016 May 18, 2016 $158
May 14, 2016 May 21, 2016 $158
May 17, 2016 May 21, 2016 $158
JetBlue Airways
Departure Date Return Date Lowest Price
Jun 10, 2016 Jun 17, 2016 $515
Spirit Airlines
Departure Date Return Date Lowest Price
May 7, 2016 May 11, 2016 $136
United Airlines
Departure Date Return Date Lowest Price
May 14, 2016 May 18, 2016 $220
Virgin America
Departure Date Return Date Lowest Price
May 31, 2016 Jun 7, 2016 $309

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 $171.

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 $136 $255
7-14 days $158 $220
14-21 days $167 $228
21-30 days $177 $226
30-60 days $182 $218
60-90 days $187 $250
90+ days $147 $241

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
$162 $158 $172 $178 $187 $136 $207

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
May Portland Chicago Spirit 5/7/16 5/11/16 0 $136
June Portland Chicago Spirit 6/4/16 6/6/16 0 $182
July Portland Chicago Spirit 7/19/16 8/2/16 0 $187
August Portland Chicago Spirit 8/10/16 8/16/16 0 $147
September Portland Chicago Spirit 9/13/16 9/20/16 0 $147
October Portland Chicago Spirit 10/4/16 10/11/16 0 $147
November Portland Chicago Spirit 11/3/16 11/6/16 0 $187
December Portland Chicago American 12/25/16 1/5/17 1 $355

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
8 9 10 11 12 13 14
$177
15 16 17 18 19 20 21
$177 $178
22 23 24 25 26 27 28
$178 $287
29 30 31 1 2 3 4
$287 $182
5 6 7 8 9 10 11
$182

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 $335.

The average price for non-stop flights from Portland to Chicago is $260.

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 3 3 3 3 3 3 3 00:05 14:50
Alaska 1 1 1 1 1 1 1 10:45 10:45
Frontier 0 1 0 1 0 1 1 00:59 00:59
Spirit 1 1 1 1 1 1 1 23:50 23:50
United 4 4 4 4 4 4 4 06:45 22:55

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 $146.

The average price for round trip flights from Portland to Chicago is $322.

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 4 hours and a minute.
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 61 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 45% of the non-stop flights between Portland and Chicago.
Question: What are the most popular connecting cities when flying from Portland to Chicago?
Answer: Denver, CO

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 MSP X X X X X X X
Frontier - X X X X
Frontier DEN X X X X X X X
Spirit - 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 DEN 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 LAS 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 $313
Portland to Milwaukee American, Alaska, Frontier, United $261
Portland to Atlanta American, Alaska, Frontier, United $323
Portland to Dallas - Ft Worth American, Alaska, Frontier, Hawaiian, Spirit, United, Virgin America $143
Portland to Detroit American, Alaska, JetBlue, Frontier, Spirit, United $322
Portland to South Bend American, United $403
Portland to Madison American, Alaska, Frontier, United $304
Portland to Minneapolis - St Paul American, Alaska, Frontier, Spirit, Sun Country, United $244
Portland to Indianapolis American, Alaska, Frontier, United $278

Cheap Domestic Flights to Chicago - CHI

FlightsAirlineLowest Price
Seattle to Chicago American, Alaska, JetBlue, Frontier, Spirit, United, Virgin America $195
Eugene to Chicago American, Alaska, United $416
Pasco to Chicago American, Alaska, United $310
Redmond to Chicago American, Alaska, United $410
Wenatchee to Chicago American, Alaska $466
Yakima to Chicago American, Alaska $542
North Bend to Chicago Alaska, United Check Dates
Seattle to Atlanta American, Alaska, Frontier, Spirit, United $368
Seattle to Milwaukee American, Alaska, Frontier, United $283
Seattle to New York American, Alaska, JetBlue, Frontier, Hawaiian, Sun Country, United, Virgin America $300
Seattle to Dallas - Ft Worth American, Alaska, Frontier, Spirit, Sun Country, United, Virgin America $243
Seattle to Detroit American, Alaska, JetBlue, Spirit, United $311
Seattle to Minneapolis - St Paul American, Alaska, Frontier, Spirit, Sun Country, United $227
Seattle to Indianapolis American, Alaska, Frontier, United $278
Seattle to Madison American, Alaska, United $451
Seattle to South Bend American, Allegiant, United $453
Seattle to St Louis American, Alaska, Frontier, United $271
Seattle to Grand Rapids American, Alaska, United $342
Seattle to Washington American, Alaska, JetBlue, Frontier, Sun Country, United, Virgin America $283
Seattle to Los Angeles American, Alaska, Spirit, United, Virgin America $106
Seattle to Cincinnati American, Alaska, United $358
Cheap Flights from Portland to Chicago, IL, United States, from $136 Round trip from PDX to CHI