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Cheap Flights from Portland to Chicago, IL, United States - PWM to CHI

Popular flights from Portland to Chicago

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
Jun 21, 2016 Jun 28, 2016 $474
JetBlue Airways
Departure Date Return Date Lowest Price
May 30, 2016 Jun 7, 2016 $318
Jun 2, 2016 Jun 7, 2016 $318
Jun 11, 2016 Jun 14, 2016 $318
United Airlines
Departure Date Return Date Lowest Price
Jun 22, 2016 Jun 28, 2016 $432

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 $361.

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.

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
$318 $374 $341 $318 $323 $318 $538

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
15 16 17 18 19 20 21
$641
22 23 24 25 26 27 28
$641
29 30 31 1 2 3 4
$641
5 6 7 8 9 10 11
$641

TIPSave $269 by flying into Milwaukee 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 $418.

The average price for non-stop flights from Portland to Chicago is $601.

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 2 4 06:01 16:43

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 $194.

The average price for round trip flights from Portland to Chicago is $418.

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 50 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 21 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)

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 ATL / MSP X X X X X X X
United - X X X X X X X
United IAD 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 $336

Cheap Domestic Flights to Chicago - CHI

FlightsAirlineLowest Price
Boston to Chicago American, Alaska, JetBlue, Spirit, United $71
Hartford to Chicago American, United $319
Providence to Chicago American, United $218
Albany to Chicago American, United $339
Burlington to Chicago American, United $322
Manchester to Chicago American, United $218
Bangor to Chicago American, United $400
Boston to Atlanta American, Alaska, Spirit, United $151
Boston to New York American, JetBlue $129
Boston to Milwaukee American, United $202
Boston to Dallas - Ft Worth American, Alaska, JetBlue, Spirit, United $83
Boston to Detroit American, JetBlue, Spirit, United $117
Boston to Indianapolis American, Alaska, United $201
Boston to Minneapolis - St Paul American, Spirit, Sun Country, United $137
Hartford to Milwaukee American, United $164
Boston to South Bend United $405
Boston to Grand Rapids American, United $192
Hartford to Atlanta American, United $161
Boston to Washington American, JetBlue, United $97
Boston to St Louis American, Alaska, United $335
Boston to Madison American, United $310
Albany to Milwaukee American, United $274
Providence to Milwaukee American, United $305
Manchester to Milwaukee American, United $304
Boston to Los Angeles American, Alaska, JetBlue, Spirit, Sun Country, United, Virgin America $323
Boston to Baltimore American, JetBlue, Spirit, United $81
Boston to Columbus American, United $184

Cheap International Flights to Chicago - CHI

FlightsAirlineLowest Price
Boston to Toronto Cape Air, American, Air Canada, Alaska, JetBlue, Spirit, Porter, Tradewind, United, WestJet $209
Boston to London American, Air Berlin, Air France, Finnair, Alitalia, JetBlue, British Airways, Condor, Aer Lingus, Eurowings, Iberia, KLM, Lufthansa, Thomas Cook, Czech, Austrian, SATA, SAS, Brussels, Tap Portugal, United, Air Europa, Virgin Atlantic, FlexFlight, City Jet, Great Lakes $744
Cheap Flights from Portland to Chicago, IL, United States, from $318 Round trip from PWM to CHI