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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: Aug 28, 2016 2:18 AM

Popular flights from Portland to Chicago Last modified: Aug 28, 2016 2:18 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.

JetBlue
PWMCHI
Wed 10/19
1 stop
CHIPWM
Thu 10/27
1 stop
$296
Select
American
PWMCHI
Tue 9/27
1 stop
CHIPWM
Tue 10/4
1 stop
$326
Select
United
PWMCHI
Fri 10/21
2 stops
CHIPWM
Mon 10/24
2 stops
$365
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 $337.

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 $945 $649
7-14 days $682 $465
14-21 days $560 $325
21-30 days $555 $326
30-60 days $555 $296
60-90 days $560 $329
90+ days $560 $303

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
$332 $305 $296 $325 $329 $330 $438

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
$945
4 5 6 7 8 9 10
$945
11 12 13 14 15 16 17
$560
18 19 20 21 22 23 24
$560 $560
25 26 27 28 29 30 1
$560 $555
2 3 4 5 6 7 8
$555
TIPSave $300 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 $333.

The average price for non-stop flights from Portland to Chicago is $555.

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 4 06:00 16:40

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 45 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.
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: 190Last modified: Aug 28, 2016 2:18 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 DCA X X X X X X X
JetBlue JFK X X X X X X X
Delta DTW 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 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, Delta, United $324

Cheap Domestic Flights to Chicago - CHI

FlightsAirlineLowest Price
Boston to Chicago American, JetBlue, Delta, Spirit, United $86
Hartford to Chicago American, Delta, United $304
Providence to Chicago American, Delta, United $177
Albany to Chicago American, Delta, United $305
Burlington to Chicago American, Delta, United $380
Manchester to Chicago American, Delta, United $177
Bangor to Chicago American, Delta, United $331
Boston to Atlanta American, Delta, Spirit, United $101
Boston to New York American, JetBlue, Delta $96
Boston to Milwaukee American, Delta, United $281
Boston to Dallas - Ft Worth American, JetBlue, Delta, Spirit, United $81
Boston to Detroit American, JetBlue, Delta, Spirit, United $108
Boston to Indianapolis American, Delta, United $177
Boston to Minneapolis - St Paul American, Delta, Spirit, Sun Country, United $202
Hartford to Milwaukee American, Delta, United $200
Boston to South Bend Delta, United $374
Boston to Grand Rapids American, Delta, United $215
Hartford to Atlanta American, Delta, United $214
Boston to Washington American, JetBlue, Delta, United $98
Boston to St Louis American, Delta, United $299
Boston to Madison American, Delta, United $329
Albany to Milwaukee American, Delta, United $284
Providence to Milwaukee American, Delta, United $271
Manchester to Milwaukee American, Delta, United $299
Boston to Los Angeles American, Alaska, JetBlue, Delta, Spirit, Sun Country, United, Virgin America $244
Boston to Baltimore American, JetBlue, Delta, Spirit, United $79
Boston to Columbus American, Delta, United $158

Cheap International Flights to Chicago - CHI

FlightsAirlineLowest Price
Boston to Toronto American, Air Canada, Alaska, Delta, Porter, United, WestJet $215
Boston to London American, Air Berlin, Air Canada, Air France, AeroMexico, Royal Air Maroc, Avianca, Finnair, Alitalia, British Airways, Cathay, Delta, Norwegian Shuttle, Aer Lingus, Emirates, Icelandair, Iberia, Latam Airlines Brasil, KLM, Lufthansa, Swiss, El Al, Austrian, SATA, SAS, Brussels, Turkish, Tap Portugal, United, Air Europa, Virgin Atlantic, WestJet, WOW air $430
Cheap Flights from Portland to Chicago, IL, United States, from $296 Round trip from PWM to CHI