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Did you mean flights from Chicago to Portland?

Cheap Flights from Portland to Chicago, IL, United States - PWM to CHI Last modified: Jul 28, 2016 2:23 AM

Popular flights from Portland to Chicago Last modified: Jul 28, 2016 2:23 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.

American
PWMCHI
Wed 10/26
1 stop
CHIPWM
Sat 10/29
1 stop
$242
Select
American
PWMCHI
Tue 11/8
1 stop
CHIPWM
Sat 11/12
1 stop
$242
Select
JetBlue
PWMCHI
Wed 8/24
1 stop
CHIPWM
Thu 8/25
1 stop
$290
Select
JetBlue
PWMCHI
Wed 8/31
1 stop
CHIPWM
Fri 9/9
1 stop
$290
Select
United
PWMCHI
Thu 8/25
2 stops
CHIPWM
Tue 8/30
2 stops
$363
Select
United
PWMCHI
Thu 9/1
2 stops
CHIPWM
Tue 9/13
2 stops
$363
Select

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 $300.

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 $798 $593
7-14 days $653 $344
14-21 days $664 $456
21-30 days $613 $290
30-60 days $613 $244
60-90 days $613 $242
90+ days $613 $242

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
$297 $244 $242 $244 $321 $298 $448

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
July Portland Chicago American 7/31/16 8/2/16 2 $707
August Portland Chicago JetBlue 8/24/16 8/25/16 1 $290
September Portland Chicago American 9/8/16 9/12/16 1 $244
October Portland Chicago American 10/26/16 10/29/16 1 $242
November Portland Chicago American 11/8/16 11/12/16 1 $242
December Portland Chicago American 12/30/16 1/1/17 1 $401
February Portland Chicago JetBlue 2/18/17 2/24/17 1 $376
March Portland Chicago JetBlue 3/15/17 3/19/17 1 $434

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
14 15 16 17 18 19 20
$613
21 22 23 24 25 26 27
$613 $613
28 29 30 31 1 2 3
$613 $613
4 5 6 7 8 9 10
$613
TIPSave $99 by flying into Indianapolis instead of Chicago from Portland

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 $298.

The average price for non-stop flights from Portland to Chicago is $613.

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 4 4 4 4 4 4 5 06:00 16:45

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 $213.

The average price for round trip flights from Portland to Chicago is $298.

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 46 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 29 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: 187Last modified: Jul 28, 2016 2:23 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 PHL 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 DTW / 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 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 $274

Cheap Domestic Flights to Chicago - CHI

FlightsAirlineLowest Price
Boston to Chicago American, Alaska, JetBlue, Spirit, United $77
Hartford to Chicago American, United $278
Providence to Chicago American, United $187
Albany to Chicago American, United $228
Burlington to Chicago American, United $340
Manchester to Chicago American, United $187
Bangor to Chicago American, United $396
Boston to Atlanta American, Spirit, United $119
Boston to New York American, JetBlue $97
Boston to Milwaukee American, United $164
Boston to Dallas - Ft Worth American, Alaska, JetBlue, Spirit, United $87
Boston to Detroit American, JetBlue, Spirit, United $127
Boston to Indianapolis American, United $177
Boston to Minneapolis - St Paul American, Alaska, Spirit, Sun Country, United $145
Hartford to Milwaukee American, United $164
Boston to South Bend United $358
Boston to Grand Rapids American, United $210
Hartford to Atlanta American, United $144
Boston to Washington American, JetBlue, United $98
Boston to St Louis American, Alaska, United $319
Boston to Madison American, Alaska, United $325
Albany to Milwaukee American, United $262
Providence to Milwaukee American, United $164
Manchester to Milwaukee American, United $224
Boston to Los Angeles American, Alaska, JetBlue, Spirit, Sun Country, United, Virgin America $261
Boston to Baltimore American, JetBlue, Spirit, United $81
Boston to Columbus American, United $157

Cheap International Flights to Chicago - CHI

FlightsAirlineLowest Price
Boston to Toronto American, Air Canada, Alaska, JetBlue, Porter, United, WestJet $223
Boston to London American, Air Berlin, Air France, Finnair, Alitalia, JetBlue, British Airways, Norwegian Air, Condor, Aer Lingus, Eurowings, Iberia, Meridiana, KLM, Lufthansa, LOT, Thomas Cook, Czech, Austrian, SATA, SAS, Brussels, Tap Portugal, United, Air Europa, Virgin Atlantic, FlexFlight $493
Cheap Flights from Portland to Chicago, IL, United States, from $242 Round trip from PWM to CHI