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Cheap Flights from Portland to Chicago, IL, United States - PWM to CHI Last modified: May 25, 2016 7:31 PM

Popular flights from Portland to Chicago Last modified: May 25, 2016 7:31 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.

American Airlines
Departure Date Return Date Lowest Price
Sep 22, 2016 Sep 24, 2016 $353
Sep 22, 2016 Sep 26, 2016 $353
JetBlue Airways
Departure Date Return Date Lowest Price
Sep 22, 2016 Sep 26, 2016 $288
United Airlines
Departure Date Return Date Lowest Price
Sep 1, 2016 Sep 5, 2016 $364
Sep 16, 2016 Sep 23, 2016 $364

How Much Does it Cost to Fly from Portland to Chicago (PWM 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 $416.

When Can I Buy the Cheapest Flight from Portland to Chicago (PWM 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 $1,091 $748
7-14 days $1,091 $446
14-21 days $687 $436
21-30 days $607 $424
30-60 days $607 $337
60-90 days $607 $396
90+ days $607 $288

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
$413 $396 $337 $402 $432 $515 $414

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 American 5/29/16 5/31/16 2 $612
June Portland Chicago JetBlue 6/29/16 7/12/16 1 $380
July Portland Chicago JetBlue 7/20/16 7/26/16 1 $337
August Portland Chicago JetBlue 8/26/16 8/29/16 1 $306
September Portland Chicago JetBlue 9/22/16 9/26/16 1 $288
October Portland Chicago JetBlue 10/9/16 10/11/16 1 $306
November Portland Chicago JetBlue 11/16/16 11/20/16 1 $331
December Portland Chicago JetBlue 12/29/16 12/31/16 1 $395

Non-Stop vs Connecting Flights from Portland to Chicago (PWM 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 $410.

The average price for non-stop flights from Portland to Chicago is $637.

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
United 3 3 3 3 3 3 4 06:00 16:50

Round Trip vs One Way Flights from Portland to Chicago (PWM 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 $195.

The average price for round trip flights from Portland to Chicago is $410.

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 2 hours and 43 minutes.
Question: How many miles are there between Portland and Chicago?
Answer: The distance from Portland to Chicago is 897 miles.
Question: How common are direct flights from Portland to Chicago?
Answer: There are 22 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 100% 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 (PWM to CHI) Number of flights searched: 172Last modified: May 25, 2016 7:31 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 CLT X X X X X X X
JetBlue JFK X X X X X X X
Delta ATL X X X X X X X
Delta ATL / MSP X X X X X X X
United - X X X X X X X
United EWR X X X X X X X
Southwest - X
Southwest BWI 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 - PWM

FlightsAirlineLowest Price
Portland to Milwaukee American, United $339

Cheap Domestic Flights to Chicago - CHI

FlightsAirlineLowest Price
Boston to Chicago American, Alaska, JetBlue, Spirit, United $97
Hartford to Chicago American, United $333
Providence to Chicago American, United $201
Albany to Chicago American, United $236
Burlington to Chicago American, United $353
Manchester to Chicago American, United $200
Bangor to Chicago American, United $486
Boston to Atlanta American, Spirit, United $171
Boston to New York American, JetBlue $97
Boston to Milwaukee American, United $164
Boston to Dallas - Ft Worth American, Alaska, JetBlue, Spirit, United $134
Boston to Detroit American, JetBlue, Spirit, United $116
Boston to Indianapolis American, United $178
Boston to Minneapolis - St Paul American, Alaska, Spirit, Sun Country, United $137
Hartford to Milwaukee American, United $267
Boston to South Bend United $410
Boston to Grand Rapids American, United $210
Hartford to Atlanta American, United $161
Boston to Washington American, JetBlue, United $127
Boston to St Louis American, Alaska, United $348
Boston to Madison American, Alaska, United $325
Albany to Milwaukee American, United $268
Providence to Milwaukee American, United $266
Manchester to Milwaukee American, United $164
Boston to Los Angeles American, Alaska, JetBlue, Spirit, Sun Country, United, Virgin America $254
Boston to Baltimore American, JetBlue, Spirit, United $81
Boston to Columbus American, United $160

Cheap International Flights to Chicago - CHI

FlightsAirlineLowest Price
Boston to Toronto Cape Air, American, Air Canada, Alaska, JetBlue, Porter, United, WestJet $208
Boston to London American, Air Berlin, Air France, Finnair, Alitalia, JetBlue, British Airways, Condor, Aer Lingus, Eurowings, Iberia, Meridiana, KLM, Lufthansa, Thomas Cook, Czech, Austrian, SATA, SAS, Brussels, Tap Portugal, United, Air Europa, Virgin Atlantic, FlexFlight $810
Cheap Flights from Portland to Chicago, IL, United States, from $288 Round trip from PWM to CHI