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Did you mean flights from Chicago to Portland?

Cheap Flights from Portland to Chicago, IL, United States - PDX to CHI Last modified: Jun 30, 2016 7:34 PM

Popular flights from Portland to Chicago Last modified: Jun 30, 2016 7:34 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.

United
PDXCHI
Wed 7/13
nonstop
CHIPDX
Tue 7/19
nonstop
$157
Select
United
PDXCHI
Wed 7/20
nonstop
CHIPDX
Tue 7/26
nonstop
$157
Select
Spirit
PDXCHI
Sun 7/3
nonstop
CHIPDX
Tue 7/12
nonstop
$167
Select
American
PDXCHI
Wed 10/26
nonstop
CHIPDX
Wed 11/2
nonstop
$187
Select
American
PDXCHI
Wed 10/26
nonstop
CHIPDX
Sat 10/29
nonstop
$187
Select
Alaska
PDXCHI
Sat 10/22
nonstop
CHIPDX
Tue 10/25
nonstop
$243
Select
Alaska
PDXCHI
Wed 10/26
nonstop
CHIPDX
Sat 10/29
nonstop
$243
Select
Alaska
PDXCHI
Fri 10/28
nonstop
CHIPDX
Tue 11/1
nonstop
$243
Select
Alaska
PDXCHI
Fri 10/28
nonstop
CHIPDX
Mon 10/31
nonstop
$243
Select
Frontier
PDXCHI
Wed 10/26
1 stop
CHIPDX
Sat 10/29
1 stop
$244
Select
Virgin America
PDXCHI
Wed 9/7
1 stop
CHIPDX
Sat 9/10
1 stop
$321
Select
Virgin America
PDXCHI
Fri 9/9
1 stop
CHIPDX
Sat 9/24
1 stop
$321
Select
Virgin America
PDXCHI
Mon 9/12
1 stop
CHIPDX
Tue 9/13
1 stop
$321
Select
Virgin America
PDXCHI
Fri 9/16
1 stop
CHIPDX
Sat 10/1
1 stop
$321
Select
JetBlue
PDXCHI
Mon 8/22
1 stop
CHIPDX
Thu 8/25
1 stop
$697
Select

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 $184.

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 $167 $229
7-14 days $157 $185
14-21 days $157 $181
21-30 days $212 $220
30-60 days $197 $195
60-90 days $197 $189
90+ days $187 $215

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
$197 $189 $157 $197 $195 $185 $167

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
June Portland Chicago Spirit 6/30/16 7/4/16 0 $417
July Portland Chicago United 7/13/16 7/19/16 0 $157
August Portland Chicago United 8/23/16 8/30/16 1 $195
September Portland Chicago United 9/13/16 9/22/16 1 $189
October Portland Chicago American 10/26/16 10/29/16 0 $187
November Portland Chicago American 11/1/16 11/5/16 0 $187
December Portland Chicago American 12/13/16 12/20/16 0 $275
March Portland Chicago Alaska 3/14/17 3/20/17 0 $323

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
3 4 5 6 7 8 9
$202
10 11 12 13 14 15 16
$202 $212
17 18 19 20 21 22 23
$212 $212
24 25 26 27 28 29 30
$212 $272
31 1 2 3 4 5 6
$272 $242
7 8 9 10 11 12 13
$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 $321.

The average price for non-stop flights from Portland to Chicago is $237.

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 00:15 14:50
Alaska 1 1 1 1 1 1 1 10:45 10:45
Spirit 1 1 1 1 1 1 1 23:56 23:56
United 5 5 5 5 5 5 5 00:37 23:16

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 $138.

The average price for round trip flights from Portland to Chicago is $309.

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 57 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 70 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 50% of the non-stop flights between Portland and Chicago.

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 $288
Portland to Milwaukee American, Alaska, Frontier, United $376
Portland to Atlanta American, Alaska, Frontier, Spirit, United $357
Portland to Dallas - Ft Worth American, Alaska, Frontier, Spirit, United, Virgin America $157
Portland to Detroit American, Alaska, JetBlue, Frontier, Spirit, United $330
Portland to South Bend American, Alaska, United $498
Portland to Madison American, Alaska, Frontier, United $320
Portland to Minneapolis - St Paul American, Alaska, Frontier, Spirit, Sun Country, United $234
Portland to Indianapolis American, Alaska, Frontier, United $239

Cheap Domestic Flights to Chicago - CHI

FlightsAirlineLowest Price
Seattle to Chicago American, Alaska, JetBlue, Frontier, Spirit, United, Virgin America $197
Eugene to Chicago American, Alaska, United $313
Pasco to Chicago American, Alaska, United $302
Redmond to Chicago American, Alaska, United $315
Wenatchee to Chicago American, Alaska $601
Yakima to Chicago American, Alaska $282
North Bend to Chicago Alaska, United $522
Seattle to Atlanta American, Alaska, JetBlue, Frontier, Spirit, United $317
Seattle to Milwaukee American, Alaska, Frontier, United $278
Seattle to New York American, Alaska, JetBlue, Frontier, Sun Country, United, Virgin America $279
Seattle to Dallas - Ft Worth American, Alaska, Frontier, Hawaiian, Spirit, Sun Country, United, Virgin America $246
Seattle to Detroit American, Alaska, JetBlue, Frontier, Spirit, United $309
Seattle to Minneapolis - St Paul American, Alaska, Frontier, Spirit, Sun Country, United $217
Seattle to Indianapolis American, Alaska, Frontier, United $351
Seattle to Madison American, Alaska, United $388
Seattle to South Bend American, United $460
Seattle to St Louis American, Alaska, Frontier, United $261
Seattle to Grand Rapids American, Alaska, United $364
Seattle to Washington American, Alaska, JetBlue, Frontier, Sun Country, United, Virgin America $266
Seattle to Los Angeles American, Alaska, Frontier, Spirit, United, Virgin America $107
Seattle to Cincinnati American, Alaska, Frontier, United $309
Cheap Flights from Portland to Chicago, IL, United States, from $157 Round trip from PDX to CHI