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Cheap Flights from Portland to Chicago, IL, United States - PDX to CHI Last modified: May 29, 2016 1:39 PM

Popular flights from Portland to Chicago Last modified: May 29, 2016 1:39 PM

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
Jun 4, 2016 Jun 7, 2016 $267
American Airlines
Departure Date Return Date Lowest Price
Jun 7, 2016 Jun 11, 2016 $217
Frontier Airlines
Departure Date Return Date Lowest Price
Jun 5, 2016 Jun 6, 2016 $118
JetBlue Airways
Departure Date Return Date Lowest Price
Aug 10, 2016 Aug 17, 2016 $718
Spirit Airlines
Departure Date Return Date Lowest Price
Jun 4, 2016 Jun 11, 2016 $157
Jun 7, 2016 Jun 11, 2016 $157
Jun 8, 2016 Jun 11, 2016 $157
United Airlines
Departure Date Return Date Lowest Price
Jul 10, 2016 Jul 15, 2016 $197
Virgin America
Departure Date Return Date Lowest Price
Aug 22, 2016 Sep 11, 2016 $400

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 $159.

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 $143 $244
7-14 days $118 $225
14-21 days $168 $275
21-30 days $178 $290
30-60 days $197 $270
60-90 days $167 $244
90+ days $167 $244

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
$212 $143 $157 $143 $177 $157 $118

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 Frontier 5/31/16 6/10/16 0 $243
June Portland Chicago Frontier 6/5/16 6/6/16 0 $118
July Portland Chicago United 7/10/16 7/15/16 0 $197
August Portland Chicago Spirit 8/10/16 8/16/16 0 $167
September Portland Chicago Spirit 9/7/16 9/13/16 0 $167
October Portland Chicago Spirit 10/11/16 10/18/16 0 $167
November Portland Chicago American 11/19/16 11/29/16 0 $305
December Portland Chicago American 12/8/16 12/12/16 0 $305

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
29 30 31 1 2 3 4
$143
5 6 7 8 9 10 11
$143 $168
12 13 14 15 16 17 18
$168 $190
19 20 21 22 23 24 25
$190 $232
26 27 28 29 30 1 2
$232 $242
3 4 5 6 7 8 9
$242

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 $405.

The average price for non-stop flights from Portland to Chicago is $246.

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 23:56 23:56
United 4 6 6 6 5 5 4 00:37 23:10

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 $150.

The average price for round trip flights from Portland to Chicago is $364.

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 58 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 69 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 43% 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) Number of flights searched: 283Last modified: May 29, 2016 1:39 PM

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
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
Southwest - X X X X X X X
Southwest STL 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 $273
Portland to Milwaukee American, Alaska, Frontier, United $278
Portland to Atlanta American, Alaska, Frontier, United $200
Portland to Dallas - Ft Worth American, Alaska, Frontier, Hawaiian, Spirit, United, Virgin America $157
Portland to Detroit American, Alaska, JetBlue, Frontier, Spirit, United $204
Portland to South Bend American, Alaska, United $500
Portland to Madison American, Alaska, Frontier, United $356
Portland to Minneapolis - St Paul American, Alaska, Frontier, Spirit, Sun Country, United $234
Portland to Indianapolis American, Alaska, Frontier, United $257

Cheap Domestic Flights to Chicago - CHI

FlightsAirlineLowest Price
Seattle to Chicago American, Alaska, JetBlue, Frontier, Spirit, United, Virgin America $188
Eugene to Chicago American, Alaska, United $274
Pasco to Chicago American, Alaska, United $402
Redmond to Chicago American, Alaska, United $334
Wenatchee to Chicago American, Alaska Check Dates
Yakima to Chicago American, Alaska $410
North Bend to Chicago Alaska, United Check Dates
Seattle to Atlanta American, Alaska, Frontier, Spirit, United $311
Seattle to Milwaukee American, Alaska, Frontier, United $274
Seattle to New York American, Alaska, JetBlue, Frontier, Sun Country, United, Virgin America $327
Seattle to Dallas - Ft Worth American, Alaska, Frontier, Spirit, Sun Country, United, Virgin America $235
Seattle to Detroit American, Alaska, JetBlue, Spirit, United $314
Seattle to Minneapolis - St Paul American, Alaska, Frontier, Spirit, Sun Country, United $197
Seattle to Indianapolis American, Alaska, Frontier, United $244
Seattle to Madison American, Alaska, Frontier, United $412
Seattle to South Bend American, JetBlue, United $450
Seattle to St Louis American, Alaska, Frontier, United $347
Seattle to Grand Rapids American, Alaska, United $364
Seattle to Washington American, Alaska, JetBlue, Frontier, Sun Country, United, Virgin America $261
Seattle to Los Angeles American, Alaska, Spirit, United, Virgin America $104
Seattle to Cincinnati American, Alaska, United $310
Cheap Flights from Portland to Chicago, IL, United States, from $118 Round trip from PDX to CHI