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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: Jun 30, 2016 7:38 PM

Popular flights from Portland to Chicago Last modified: Jun 30, 2016 7:38 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
PWMCHI
Thu 9/8
1 stop
CHIPWM
Sun 9/11
1 stop
$241
Select
JetBlue
PWMCHI
Thu 9/22
1 stop
CHIPWM
Mon 9/26
1 stop
$345
Select
United
PWMCHI
Thu 8/18
2 stops
CHIPWM
Sat 8/20
2 stops
$357
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 $351.

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 $1,097 $648
7-14 days $755 $544
14-21 days $623 $414
21-30 days $613 $412
30-60 days $613 $333
60-90 days $613 $241
90+ days $613 $275

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
$333 $410 $351 $241 $273 $402 $445

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 United 7/22/16 7/27/16 2 $408
August Portland Chicago American 8/29/16 9/4/16 1 $333
September Portland Chicago American 9/8/16 9/11/16 1 $241
October Portland Chicago American 10/8/16 10/13/16 1 $275
November Portland Chicago American 11/9/16 11/12/16 1 $302
December Portland Chicago JetBlue 12/25/16 1/3/17 1 $348
January Portland Chicago American 1/31/17 2/2/17 1 $454
February Portland Chicago American 2/9/17 2/11/17 1 $454

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
10 11 12 13 14 15 16
$693
17 18 19 20 21 22 23
$693 $663
24 25 26 27 28 29 30
$663
31 1 2 3 4 5 6
$613
7 8 9 10 11 12 13
$613

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 $314.

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 5 4 05:50 17:00

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 $176.

The average price for round trip flights from Portland to Chicago is $314.

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 44 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 28 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.

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 $244

Cheap Domestic Flights to Chicago - CHI

FlightsAirlineLowest Price
Boston to Chicago American, Alaska, JetBlue, Spirit, United $81
Hartford to Chicago American, United $339
Providence to Chicago American, United $247
Albany to Chicago American, United $339
Burlington to Chicago American, United $285
Manchester to Chicago American, United $144
Bangor to Chicago American, United $284
Boston to Atlanta American, Spirit, United $127
Boston to New York American, JetBlue $103
Boston to Milwaukee American, United $164
Boston to Dallas - Ft Worth American, Alaska, JetBlue, Spirit, United $98
Boston to Detroit American, JetBlue, Spirit, United $127
Boston to Indianapolis American, United $178
Boston to Minneapolis - St Paul American, Alaska, Spirit, Sun Country, United $191
Hartford to Milwaukee American, United $256
Boston to South Bend United $374
Boston to Grand Rapids American, United $210
Hartford to Atlanta American, United $158
Boston to Washington American, JetBlue, United $108
Boston to St Louis American, Alaska, United $320
Boston to Madison American, Alaska, United $326
Albany to Milwaukee American, United $264
Providence to Milwaukee American, United $224
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 $160

Cheap International Flights to Chicago - CHI

FlightsAirlineLowest Price
Boston to Toronto Cape Air, American, Air Canada, Alaska, JetBlue, Porter, United, WestJet $217
Boston to London American, Air Berlin, Air France, Finnair, Alitalia, JetBlue, British Airways, Norwegian Air, Condor, Aer Lingus, Eurowings, Iberia, Meridiana, KLM, Lufthansa, Thomas Cook, Czech, Austrian, SATA, SAS, Brussels, Corsair, Tap Portugal, United, Air Europa, Virgin Atlantic, FlexFlight $493
Cheap Flights from Portland to Chicago, IL, United States, from $241 Round trip from PWM to CHI