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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: Aug 28, 2016 2:12 AM

Popular flights from Portland to Chicago Last modified: Aug 28, 2016 2:12 AM

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
Sun 9/4
nonstop
CHIPDX
Sat 9/10
nonstop
$144
Select
American
PDXCHI
Tue 10/25
nonstop
CHIPDX
Wed 11/2
nonstop
$147
Select
Spirit
PDXCHI
Sun 10/2
nonstop
CHIPDX
Tue 10/11
nonstop
$154
Select
Spirit
PDXCHI
Sun 10/2
nonstop
CHIPDX
Mon 10/10
nonstop
$154
Select
Alaska
PDXCHI
Tue 9/27
nonstop
CHIPDX
Tue 10/4
nonstop
$233
Select
Alaska
PDXCHI
Wed 9/28
nonstop
CHIPDX
Sat 10/1
nonstop
$233
Select
Frontier
PDXCHI
Tue 9/20
1 stop
CHIPDX
Wed 10/5
1 stop
$244
Select
Frontier
PDXCHI
Tue 9/27
1 stop
CHIPDX
Tue 10/4
1 stop
$244
Select
Frontier
PDXCHI
Sat 10/1
1 stop
CHIPDX
Sat 10/8
1 stop
$244
Select
Frontier
PDXCHI
Wed 10/5
1 stop
CHIPDX
Tue 10/11
1 stop
$244
Select
Frontier
PDXCHI
Wed 10/5
1 stop
CHIPDX
Tue 10/18
1 stop
$244
Select
Virgin America
PDXCHI
Wed 9/28
1 stop
CHIPDX
Wed 10/5
1 stop
$282
Select
JetBlue
PDXCHI
Wed 9/28
1 stop
CHIPDX
Wed 10/5
1 stop
$390
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 $152.

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 $157 $227
7-14 days $144 $199
14-21 days $157 $245
21-30 days $156 $244
30-60 days $147 $194
60-90 days $157 $195
90+ days $227 $235

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
$157 $147 $157 $157 $155 $147 $144

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
August Portland Chicago Spirit 8/30/16 9/8/16 0 $182
September Portland Chicago United 9/4/16 9/10/16 0 $144
October Portland Chicago American 10/25/16 11/2/16 0 $147
November Portland Chicago Spirit 11/1/16 11/8/16 0 $157
December Portland Chicago Alaska 12/2/16 12/5/16 1 $251
January Portland Chicago American 1/6/17 1/8/17 0 $227
February Portland Chicago American 2/9/17 2/13/17 0 $227
March Portland Chicago American 3/6/17 3/11/17 1 $283

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
28 29 30 31 1 2 3
$182
4 5 6 7 8 9 10
$182 $157
11 12 13 14 15 16 17
$157 $157
18 19 20 21 22 23 24
$157 $157
25 26 27 28 29 30 1
$157 $157
2 3 4 5 6 7 8
$157

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 $258.

The average price for non-stop flights from Portland to Chicago is $189.

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 2 2 2 2 2 2 2 08:00 13:22
Alaska 1 1 1 1 1 1 1 10:45 10:45
Spirit 1 1 1 1 1 1 1 23:59 23:59
United 4 4 4 4 4 4 4 06:15 23:25

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 $130.

The average price for round trip flights from Portland to Chicago is $235.

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 56 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.
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: 289Last modified: Aug 28, 2016 2:12 AM

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
Delta MSP / CVG 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 DEN 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, Delta, Frontier, Spirit, Sun Country, United, Virgin America $322
Portland to Milwaukee American, Alaska, Delta, Frontier, United $239
Portland to Atlanta American, Alaska, Delta, Frontier, United $312
Portland to Dallas - Ft Worth American, Alaska, Delta, Frontier, Spirit, Sun Country, United, Virgin America $122
Portland to Detroit American, Alaska, JetBlue, Delta, Frontier, Spirit, United $244
Portland to South Bend Delta, United $392
Portland to Madison American, Alaska, Delta, Frontier, United $326
Portland to Minneapolis - St Paul American, Alaska, Delta, Frontier, Spirit, Sun Country, United $244
Portland to Indianapolis American, Alaska, Delta, Frontier, United $239

Cheap Domestic Flights to Chicago - CHI

FlightsAirlineLowest Price
Seattle to Chicago American, Alaska, JetBlue, Delta, Frontier, Spirit, United, Virgin America $117
Eugene to Chicago American, Alaska, Delta, United $310
Pasco to Chicago American, Alaska, Delta, United $288
Redmond to Chicago American, Alaska, Delta, United $308
Wenatchee to Chicago American, Alaska, Delta $310
Yakima to Chicago American, Alaska, Delta $282
North Bend to Chicago Alaska, United $492
Seattle to Atlanta American, Alaska, Delta, Frontier, Spirit, United $271
Seattle to Milwaukee American, Alaska, Delta, Frontier, United $304
Seattle to New York American, Alaska, JetBlue, Delta, Frontier, Sun Country, United, Virgin America $274
Seattle to Dallas - Ft Worth American, Alaska, Delta, Frontier, Spirit, Sun Country, United, Virgin America $194
Seattle to Detroit American, Alaska, JetBlue, Delta, Frontier, Spirit, United $244
Seattle to Minneapolis - St Paul American, Alaska, Delta, Frontier, Spirit, Sun Country, United $244
Seattle to Indianapolis American, Alaska, Delta, Frontier, United $234
Seattle to Madison American, Alaska, Delta, Frontier, United $373
Seattle to South Bend Delta, United $391
Seattle to St Louis American, Alaska, Delta, Frontier, United $247
Seattle to Grand Rapids American, Alaska, Delta, United $367
Seattle to Washington American, Alaska, JetBlue, Delta, Frontier, Sun Country, United, Virgin America $244
Seattle to Los Angeles American, Alaska, Delta, Spirit, United, Virgin America $81
Seattle to Cincinnati American, Alaska, Delta, Frontier, United $324
Cheap Flights from Portland to Chicago, IL, United States, from $144 Round trip from PDX to CHI