Cheap flights from Chicago (CHI) to Portland (PDX)

CHI — PDX
Aug 16 — Aug 231

The best prices from Chicago to Portland are usually found in January or October, booked 60 days in advance, depart on a Wednesday or Friday and return on a Saturday

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 2022: compare Chicago to Portland flight prices with the expected peak season, weather and rainfall in Portland.

CHI - PDX

Price

$217 - $581

PDX

Temperature

41 - 69.8 °F

PDX

Rainfall

0.7 - 5.6 inches

Popular inJuneHigh demand for flights, 42% potential price rise
Cheapest inJanuaryBest time to find cheap flights, 36% potential price drop
Round-trip from$217From Chicago (CHI) to Portland
One-way from$130One-way flight from Chicago (CHI) to Portland

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 31% on the cost of booking your flights compared to booking on days of the week where this route is of high demand.

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 58 days before your planned departure. Booking around this time can save you about 65% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $428 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $640.

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

Our data shows that January tends to be the cheapest month to fly to Portland from Chicago. Users have commonly found prices around $340 for the month, but tickets can be as low as $129. Due to multiple factors, prepare for potentially higher prices in June.

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

Unlike in the morning, when flights are generally more expensive, you can save up to 13% on flights from Chicago to Portland by exploring options for tickets in the evening.

Cheap flights from Chicago to Portland in August, September 2022

The best prices found for CHI to PDX flights for August, September
Sep 27 - Sep 30
MDW

Chicago Midway

PDX

Portland

1 stop

16h 00m
PDX

Portland

MDW

Chicago Midway

1 stop

11h 32m
$161

Frontier

Pick Dates

Deal found 22年8月8日

Sep 7 - Sep 9
MDW

Chicago Midway

PDX

Portland

1 stop

16h 01m
PDX

Portland

MDW

Chicago Midway

1 stop

11h 32m
$164

Frontier

Pick Dates

Deal found 22年8月9日

Sep 7 - Sep 10
MDW

Chicago Midway

PDX

Portland

1 stop

16h 01m
PDX

Portland

MDW

Chicago Midway

1 stop

10h 11m
$168

Frontier

Pick Dates

Deal found 22年8月9日

Chicago to Portland 2022 flight deals

Cheap flights to Portland from Chicago found for this year
Oct 3 - Oct 14
MDW

Chicago Midway

PDX

Portland

1 stop

15h 53m
PDX

Portland

MDW

Chicago Midway

1 stop

11h 17m
$161

Frontier

Pick Dates

Deal found 22年8月8日

Oct 26 - Nov 1
MDW

Chicago Midway

PDX

Portland

1 stop

15h 54m
PDX

Portland

MDW

Chicago Midway

1 stop

10h 28m
$162

Frontier

Pick Dates

Deal found 22年8月9日

Sep 7 - Sep 9
MDW

Chicago Midway

PDX

Portland

1 stop

16h 01m
PDX

Portland

MDW

Chicago Midway

1 stop

11h 32m
$164

Frontier

Pick Dates

Deal found 22年8月9日

Cheap Spirit Airlines flights from Chicago to Portland

Sep 8 - Sep 13
ORD

Chicago O'Hare Intl

PDX

Portland

1 stop

12h 19m
PDX

Portland

ORD

Chicago O'Hare Intl

2 stops

15h 54m
$238

Spirit Airlines

Pick Dates

Deal found 22年8月9日

Sep 23 - Sep 26
ORD

Chicago O'Hare Intl

PDX

Portland

1 stop

12h 19m
PDX

Portland

ORD

Chicago O'Hare Intl

1 stop

6h 45m
$239

Spirit Airlines

Pick Dates

Deal found 22年8月9日

Sep 28 - Oct 2
ORD

Chicago O'Hare Intl

PDX

Portland

1 stop

7h 12m
PDX

Portland

ORD

Chicago O'Hare Intl

1 stop

12h 46m
$240

Spirit Airlines

Pick Dates

Deal found 22年8月8日

  • If you’re traveling from Chicago to Portland, one of the more common airlines traveling that route is Spirit Airlines. Chicago to Portland flights are typically 89% cheaper than other airlines traveling the same route. Flights from Spirit Airlines typically cost $266.79 RT. The cheapest Spirit Airlines flight found for this route was $118. When traveling from Chicago to Portland on Spirit Airlines, the most popular airport to depart from is Chicago O'Hare Intl Airport and the most popular airport to arrive at is Portland Airport. When flying from Chicago to Portland, Spirit Airlines flights are 23% more popular than any other airline flying that same route.

Cheap Frontier flights from Chicago to Portland

Oct 3 - Oct 7
MDW

Chicago Midway

PDX

Portland

1 stop

15h 53m
PDX

Portland

MDW

Chicago Midway

1 stop

11h 17m
$161

Frontier

Pick Dates

Deal found 22年8月8日

Oct 26 - Nov 1
MDW

Chicago Midway

PDX

Portland

1 stop

15h 54m
PDX

Portland

MDW

Chicago Midway

1 stop

10h 28m
$162

Frontier

Pick Dates

Deal found 22年8月9日

Sep 7 - Sep 9
MDW

Chicago Midway

PDX

Portland

1 stop

16h 01m
PDX

Portland

MDW

Chicago Midway

1 stop

11h 32m
$164

Frontier

Pick Dates

Deal found 22年8月9日

  • One of the most popular airlines traveling from Chicago to Portland is Frontier. Flights from Frontier traveling this route typically cost $445.45 RT. This price is typically 36% cheaper than other airlines that offer Chicago to Portland flights. When booking this route, the cheapest RT price found was $177. Chicago O'Hare Intl Airport is the most common Chicago airport to take off from when flying to Portland. Portland Airport is the most popular arrival airport in Portland. When flying from Chicago to Portland, Frontier flights are 19% more popular than any other airline flying that same route.

Non-stop flights to Portland from Chicago

Save time with Chicago to Portland direct flight deals
Nov 9 - Nov 15
ORD

Chicago O'Hare Intl

PDX

Portland

Nonstop

4h 28m
PDX

Portland

ORD

Chicago O'Hare Intl

Nonstop

3h 56m
$258

American Airlines

Pick Dates

Deal found 22年8月10日

Nov 5 - Nov 12
ORD

Chicago O'Hare Intl

PDX

Portland

Nonstop

4h 28m
PDX

Portland

ORD

Chicago O'Hare Intl

Nonstop

3h 56m
$278

American Airlines

Pick Dates

Deal found 22年8月10日

Oct 14 - Oct 18
ORD

Chicago O'Hare Intl

PDX

Portland

Nonstop

4h 28m
PDX

Portland

ORD

Chicago O'Hare Intl

Nonstop

3h 53m
$288

United Airlines

Pick Dates

Deal found 22年8月11日

Last minute flights from Chicago to Portland

Late deals on return flights to Portland from Chicago, departing today and this week
Aug 19 - Aug 25
MDW

Chicago Midway

PDX

Portland

1 stop

15h 46m
PDX

Portland

MDW

Chicago Midway

2 stops

18h 47m
$273

Frontier

Pick Dates

Deal found 22年8月9日

Aug 17 - Aug 29
MDW

Chicago Midway

PDX

Portland

1 stop

9h 19m
PDX

Portland

MDW

Chicago Midway

1 stop

16h 15m
$314

Frontier

Pick Dates

Deal found 22年8月10日

Aug 19 - Aug 25
MDW

Chicago Midway

PDX

Portland

1 stop

15h 46m
PDX

Portland

MDW

Chicago Midway

1 stop

16h 38m
$324

Frontier

Pick Dates

Deal found 22年8月9日

One-way flights to Portland from Chicago

The cheapest one-way flights from Chicago to Portland
Sep 12
MDW

Chicago Midway

PDX

Portland

1 stop

15h 53m
$86

Frontier

Pick Dates

Deal found 22年8月8日

Oct 4
MDW

Chicago Midway

PDX

Portland

1 stop

15h 57m
$90

Frontier

Pick Dates

Deal found 22年8月9日

Oct 22
MDW

Chicago Midway

PDX

Portland

2 stops

14h 50m
$95

Frontier

Pick Dates

Deal found 22年8月10日

Related info for your journey

Useful info, stats and facts about Chicago to Portland flights.

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 23 inbound flights from Chicago per day. 10 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 $161, but on average you can expect to pay $187.

Are there nonstop flights from Chicago to Portland for under $300 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to Portland under $300. A good price for a nonstop flight from Chicago to Portland is less than $318.

Are there last-minute flights available from Chicago to Portland for under $300?

There are currently 20+ open flights from Chicago to Portland within the next 7 days for less than $300.

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 10 flights from Chicago to Portland on average per day.
Evening (6pm - Midnight) - 100% of flight departures

How long is the flight from Chicago to Portland?

Airlines like Frontier fly from Chicago to Portland in about 15h 53m. The time it takes to get you to your destination can typically vary by up to . Airlines will cover a distance of 1744 mi.

What is the cheapest airline to fly 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 $161 on this airline. This flight start at 52% lower than the current average price 3 months from now.

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 American Airlines, Alaska Airlines or Delta 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 Alaska Airlines (82%), United Airlines (79%) and Air Canada (79%).

What are the cheapest flights from Chicago to Portland?

Looking at all options, your cheapest flight can be booked for $195. While the most popular route (Chicago O'Hare Intl - Portland) can be booked for $236 on average our data indicates $787 when flying from Chicago to Portland.

Alternative routes for Chicago to Portland

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

Top 8 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.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Juneyao AirlinesCheapest$14Average$21FlexibilityNo cancel feeOn-time66%COVID-19 safety
Search Juneyao Airlines flights
Spirit AirlinesCheapest$82Average$335FlexibilityNo cancel feeOn-time65%COVID-19 safety
Search Spirit Airlines flights
FrontierCheapest$83Average$145FlexibilityNo cancel feeOn-time62%COVID-19 safety
Search Frontier flights
Sun Country AirCheapest$117Average$474FlexibilityNo cancel feeOn-time83%COVID-19 safety
Search Sun Country Air flights
Alaska AirlinesCheapest$118Average$267FlexibilityNo cancel feeOn-time75%COVID-19 safety
Search Alaska Airlines flights
DeltaCheapest$127Average$486FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights
American AirlinesCheapest$163Average$394FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
United AirlinesCheapest$177Average$445FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights

Hourly flight availability from Chicago to Portland

See what time of day planes typically take off from Chicago to Portland
1%of flight departuresEarly morningMidnight to 6 am
35%of flight departuresMorning6 am to noon
29%of flight departuresAfternoonNoon to 6 pm
35%of flight departuresEvening6 pm to midnight
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
Sunday23daily flights
Monday18daily flights
Tuesday20daily flights
Wednesday25daily flights
Thursday27daily flights
Friday24daily flights
Saturday25daily flights