Cheap flights from Chicago to Portland (CHI - PDX)

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The best prices from Chicago to Portland are usually found in August or April, booked 29 days in advance, depart on a Wednesday or Tuesday and return on a Friday

How to find the cheapest flight from
Chicago (CHI) to Portland (PDX)

All the information you need to plan the best CHI to PDX flight in 2021: compare Chicago to Portland flight prices with the expected peak season, weather and rainfall in Portland.
CHI - PDX
Price
$236 - $334
PDX
Temperature
41 - 69.8 °F
PDX
Precipitation
0.7 - 5.6 inches

Popular in

December

High demand for flights, 19% potential price rise

Cheapest in

August

Best time to find cheap flights, 13% potential price drop

Round-trip from

$236

From Chicago (CHI) to Portland

One-way from

$108

One-way flight from Chicago (CHI) to Portland

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
How far in advance should I book a flight from Chicago to Portland?

To save on the cost of your flight from Chicago to Portland, book at least 27 days before your planned departure. Booking around this time can save you about 20% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $279 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $315.

When is the cheapest time to fly from Chicago to Portland (CHI - PDX)?

Unlike in the evening, when flights are generally more expensive, you can save up to 28% on flights from Chicago to Portland by exploring options for tickets at noon.

What is the cheapest day to fly round-trip from Chicago to Portland?

Travelers have found that booking a Tuesday departure is the best way to save up to 11% on the cost of booking your flights compared to booking on days of the week where this route is of high demand.

What is the cheapest month to fly from Chicago to Portland?

Our data shows that August tends to be the cheapest month to fly to Portland from Chicago. Users have commonly found prices around $272 for the month, but tickets can be as low as $119. Due to multiple factors, prepare for potentially higher prices in December.

Cheap flights from Chicago to Portland in November, December 2021

The best prices found for CHI to PDX flights for November, December
8 Dec - 13 Dec
$122pp
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PDX
Portland
PDX
Portland
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
4 Dec - 6 Dec
$123pp
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PDX
Portland
PDX
Portland
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl
8 Dec - 13 Dec
$130pp
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
PDX
Portland
PDX
Portland
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl

Chicago to Portland 2022 flight deals

Cheap flights to Portland from Chicago found for next year
9 Dec - 12 Dec
$294pp
MDW
Chicago Midway
Delta
 
1 STOP
PDX
Portland
PDX
Portland
Delta
 
1 STOP
MDW
Chicago Midway
10 Dec - 12 Dec
$304pp
MDW
Chicago Midway
Delta
 
1 STOP
PDX
Portland
PDX
Portland
Delta
 
1 STOP
MDW
Chicago Midway
8 Dec - 9 Dec
$313pp
MDW
Chicago Midway
Delta
 
1 STOP
PDX
Portland
PDX
Portland
Delta
 
1 STOP
MDW
Chicago Midway

Non-stop flights to Portland from Chicago

Save time with Chicago to Portland direct flight deals
11 Jan - 1 Feb
$196pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
PDX
Portland
PDX
Portland
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
5 Feb - 12 Feb
$197pp
ORD
Chicago O'Hare Intl
Alaska Airlines
Non-Stop
PDX
Portland
PDX
Portland
Alaska Airlines
Non-Stop
ORD
Chicago O'Hare Intl
13 Jan - 16 Jan
$206pp
ORD
Chicago O'Hare Intl
Alaska Airlines
Non-Stop
PDX
Portland
PDX
Portland
Alaska Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Last minute flights from Chicago to Portland

Late deals on round-trip flights to Portland from Chicago, departing today and this week
3 Dec - 5 Dec
$441pp
MDW
Chicago Midway
Delta
 
1 STOP
PDX
Portland
PDX
Portland
Delta
 
1 STOP
MDW
Chicago Midway
4 Dec - 7 Dec
$500pp
MDW
Chicago Midway
Delta
   
2 STOPS
PDX
Portland
PDX
Portland
Delta
 
1 STOP
MDW
Chicago Midway
1 Dec - 4 Dec
$569pp
MDW
Chicago Midway
Delta
 
1 STOP
PDX
Portland
PDX
Portland
Delta
 
1 STOP
MDW
Chicago Midway

One-way flights to Portland from Chicago

The cheapest one-way flights from Chicago to Portland
2:05 am - 7:20 am
Alaska Airlines
1 Stop
7h 15m
ORD - PDX
Alaska Airlines
1:45 am - 7:09 pm
Multiple Airlines
2 Stops
19h 24m
ORD - PDX
Multiple Airlines
$110
Kiwi.com
6:04 pm - 3:38 am
Frontier
2 Stops
35h 34m
ORD - PDX
Frontier
$112
Kiwi.com

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Chicago</span> to <span class="emphasized">Portland</span> flights.

Flight FAQs

From Chicago to Portland

What airport do you fly into for flights to Portland from Chicago?

For a flight from Chicago to Portland, you will be flying into Portland. Portland (PDX) is just 6.0 mi from the center of the city. Portland is the only Portland airport and it handles 10 inbound flights from Chicago per day. 9 airlines have flights to Portland from Chicago on a regular basis.

Which airlines flying from Chicago to Portland have flexible cancellations due to COVID-19?

United Airlines, Alaska Airlines, and American Airlines are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

Can I find flights from Chicago to Portland for under $200 on Cheapflights?

Yes, there are multiple flights from Chicago to Portland for under $200. The cheapest flight booked recently is on Frontier for just $122, but on average you can expect to pay $141.

Are there nonstop flights from Chicago to Portland for under $200 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to Portland under $200. A good price for a nonstop flight from Chicago to Portland is less than $241.

Are there last-minute flights available from Chicago to Portland for under $500?

There are currently 20+ open flights from Chicago to Portland within the next 7 days for less than $500.

What days are nonstop flights available from Chicago to Portland?

Nonstop flights can be found on the following days: Sunday, Monday, Thursday, Friday, Saturday.

How many flights depart from Chicago to Portland on average per day?

Travelers can expect 27 flights from Chicago to Portland on average per day.
Morning (6am - Noon) - 7% of flight departures
Afternoon (Noon - 6pm) - 4% of flight departures
Evening (6pm - Midnight) - 89% of flight departures

How long is the flight from Chicago to Portland?

Airlines like Frontier and Spirit Airlines fly from Chicago to Portland in about 10h 32m. The time it takes to get you to your destination can typically vary by up to 1h 54m. Airlines will cover a distance of 1744 mi. This flight may include one or multiple stops.

What are the cheapest airlines flying from Chicago to Portland round-trip?

Our cheapest airline available from Chicago to Portland is Frontier. Our recent data shows that you can find tickets from as low as $122 on this airline. An additional option worth looking into is Spirit Airlines, starting at $159. These flights start at 55% lower than the current average price 3 months from now.

What are the cheapest airlines to fly from Chicago to Portland one-way?

For one-way options, check prices for Frontier. According to our data, you can fly for as low as $60. Users have also found prices from $74 and $87 on Spirit Airlines and Alaska Airlines, respectively.

What are the most popular airlines that fly from Chicago to Portland?

When booking a flight from Chicago to Portland, you may want to consider flying on Major Airline, American Airlines or Alaska Airlines as they are the most popular for this route.

What are the most reliable airlines from Chicago to Portland?

The top 3 most reliable airlines when flying from Chicago to Portland are Air Canada (89%), Brussels Airlines (88%) and United Airlines (87%).

What are the cheapest flights from Chicago to Portland?

Looking at all options, your cheapest flight can be booked for $84. While the most popular route (Chicago O'Hare Intl - Portland) can be booked for $139 on average our data indicates $461 when flying from Chicago to Portland.

COVID Restrictions

View COVID Travel Restrictions for Portland, OR

Do I need a COVID test to fly to Portland from Chicago?

Information is based on travel restrictions for travel to Portland within the United States

Most visitors from Chicago need to provide a negative COVID-19 test result and/or quarantine to enter Portland.

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Portland.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Portland.

Do I need a test to fly back to Chicago from Portland?

Returning to Chicago from Portland

COVID-19 testing requirements
Visitors from Portland must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago.

Quarantine requirements
Visitors from Portland are not required to quarantine after entering Chicago.

Hide COVID Travel Restrictions for Portland, OR

Alternative routes for Chicago to Portland

See prices for flight routes from nearby airports that may be better suited for you.

Destination information for Portland

Things to know before you go - useful duration and weather info for your trip from Chicago to Portland.
Average temperature for November in Portland
53.6 °F
Avg rainfall for November in Portland
5.4 ″

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Airports servicing Portland

Top 7 airlines flying from Chicago to Portland

The chart below displays the airlines Cheapflights users traveling from Chicago to Portland choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Frontier
$96 $206 No cancel fee 62%
Spirit Airlines
$116 $244 No cancel fee 65%
Sun Country Air
$131 $239 No cancel fee 83%
Delta
$134 $379 No cancel fee N/A
American Airlines
$140 $312 No cancel fee 71%
Alaska Airlines
$140 $283 No cancel fee 75%
United Airlines
$140 $357 No cancel fee 69%

Hourly flight availability from Chicago to Portland

See what time of day planes typically take off from Chicago towards Portland.
Morning 6 AM to noon 48% of CHI to PDX departures
Evening 6 PM to midnight 27% of CHI to PDX departures
Afternoon Noon to 6 PM 18% of CHI to PDX departures
Early morning Midnight to 6 AM 7% of CHI to PDX departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Chicago to Portland
See how many times per day planes take to the skies headed from Chicago to Portland.
Sunday
11 daily flights
Monday
15 daily flights
Tuesday
16 daily flights
Wednesday
18 daily flights
Thursday
4 daily flights
Friday
7 daily flights
Saturday
5 daily flights
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