Flights
Hotels
From
To
1 traveler
Unsupported Browser!
Find Flights
Finding cheap flights is simple. More than 36 million people last year saved hundreds by using our flights tool.

Flights
Hotels
Round-trip
One-way
1 traveler
Unsupported Browser!
Find Flights
Finding cheap flights is simple. More than 36 million people last year saved hundreds by using our flights tool.
Did you mean flights from Chicago to Portland?

Flights from Portland to Chicago, United States Last modified: Dec 5, 2016 2:37 -05:00

Portland to Chicago Last modified: Dec 5, 2016 2:37 -05:00Prices shown were found by travelers like you over the past 30 days

We've scanned 22,736,586,123 round trip itineraries and found the cheapest flights from Portland to Chicago. American & United frequently offer the best deals on Portland to Chicago flights, or select your preferred carrier below to see the cheapest days to fly.

American
PWMCHI
Fri 1/27
1 stop
CHIPWM
Sun 1/29
1 stop
$201
United
PWMCHI
Wed 1/25
1 stop
CHIPWM
Sat 1/28
1 stop
$202
JetBlue
PWMCHI
Thu 3/16
1 stop
CHIPWM
Mon 3/20
1 stop
$319

How Much is a Flight from Portland to Chicago? Prices shown were found by travelers like you over the past 30 days

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 $256.

Where To Buy Cheap Flights from Portland to Chicago?

The best way to find a great deal on airfare is to search multiple sites. When you run a search on FareCompare, we search multiple sites and fare sources all at once so you don't have to - which is why we thinking FareCompare is the best place to find cheap tickets. Airlines can adjust prices for 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 found that Tuesdays, Wednesdays, and Saturdays are often the best days to book flights. If you'd like to learn more, read our article about the best time to buy airline tickets.

How far in advance should I book tickets from Portland to Chicago? Prices shown were found by travelers like you over the past 30 days

The chart below shows up-to-date information regarding how far in advance to book your flight from Portland to Chicago.

Non Stop versus Connecting
Advanced PurchaseNon StopConnecting
< 7 days $0 $0
7-14 days $761 $263
14-21 days $689 $370
21-30 days $660 $343
30-60 days $629 $201
60-90 days $629 $204
90+ days $629 $201

Cheapest Day To Fly from Portland to Chicago Prices shown were found by travelers like you over the past 30 days

We've examined 22,742,432,069 itinerary searches that we've seen for departures in the next 90 days and found that the cheapest day to fly from Portland to Chicago is Friday. See the chart below to compare prices for other days of the week.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$262 $278 $202 $204 $201 $435 $204

Compare Flight Prices from Portland to Chicago by Month Prices shown were found by travelers like you over the past 30 days

Low priced flights are most commonly available by purchasing between one and three months in advance. International or holiday flights may need to be purchased even further in advance. The chart below shows the cheapest flight prices by month for Portland to Chicago flights.

Month Origin Destination Carrier Depart Date Return Date Stops Price
December Portland Chicago American 12/16/16 12/19/16 1 $263
January Portland Chicago American 1/27/17 1/29/17 1 $201
February Portland Chicago American 2/2/17 2/6/17 1 $204
March Portland Chicago United 3/21/17 3/28/17 1 $204
April Portland Chicago United 4/11/17 4/18/17 1 $312
May Portland Chicago American 5/2/17 5/10/17 1 $201

Cheap Last Minute Flights from Portland to Chicago Prices shown were found by travelers like you over the past 30 days

Looking for cheap last minute flights or a weekend getaway? We've got you covered with weekend flight deals from Portland to Chicago. The chart below shows the best last minute deals and cheap flights this weekend we could find.

Next 30 Days

SunMonTueWedThuFriSat
11 12 13 14 15 16 17
$263
18 19 20 21 22 23 24
$263 $520
25 26 27 28 29 30 31
$520
1 2 3 4 5 6 7
$356
8 9 10 11 12 13 14
$356

Connecting Flights vs Direct Flights from Portland to Chicago Prices shown were found by travelers like you over the past 30 days

Flights between some cities may be significantly cheaper if you choose 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 $241.

The average price for direct flights from Portland to Chicago is $637.

The chart below shows up to date information regarding non-stop flights from Portland to Chicago.

Weekly Direct Flights from Portland to Chicago - By Carrier
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
United 3 3 5 1 2 2 3 05:45 16:25

One Way Flights vs Round Trip Flights from Portland to Chicago Prices shown were found by travelers like you over the past 30 days

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 not available.

The average price for round trip flights from Portland to Chicago is $230.

Portland to Chicago Flight Questions

Below are some common questions that asked about this flight route:

Question: How long is the flight from Portland to Chicago?
Answer: The average Portland to Chicago flight time is 3 hours and 2 minutes.
Question: How far is Chicago from Portland?
Answer: The distance from Portland to Chicago is 897 miles (1,443 kilometers).
Question: How common are direct flights from Portland to Chicago?
Answer: There are 15 direct flights from Portland to Chicago.
Question: What are the most popular Portland airlines for direct 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: Newark, NJ

Airlines in Portland flying to Chicago Last modified: Dec 5, 2016 2:37 -05:00Number of routes searched: 151Number of itineraries searched: 30,811

Wondering which airlines fly out of Portland to Chicago? We've gathered the average price of Portland airlines with flights to Chicago. Different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Below is the full flight schedule summary showing which days of the week individual carriers offer flights for the next 30 days.

Portland to Chicago
Airline Connections Mon Tue Wed Thu Fri Sat Sun
United -
American CLT
American DCA
American DTW
American PHL
American PIT
JetBlue JFK
Delta ATL
Delta DTW
United BUF
United CHS
United DTW
United EWR

Portland to Chicago Airports

These are the major commercial airports we're currently monitoring in Portland and Chicago. If your route includes a city with multiple airports, you may be able to find substantial savings by choosing an alternate airport.

Farecompare Research Tools

FareCompare's Flight Schedule Search Tool helps you find information about airline schedule filings, including flight numbers, depart times, and travel distance.

Cheap Domestic Flights from Portland - PWM Last modified: Dec 5, 2016 2:37 -05:00Prices shown were found by travelers like you over the past 30 days

FlightsLowest Price
Portland to Milwaukee$426

Cheap International Flights to Chicago - CHI Last modified: Dec 5, 2016 2:37 -05:00Prices shown were found by travelers like you over the past 30 days

Cheap Flights from Portland to Chicago