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$108+ Cheap flights from Chicago (CHI) to Portland (PDX)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
dic. 23 — dic. 301
lun. 12/23
lun. 12/30
1 adult, Economy
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The best prices from Chicago to Portland are usually found in September or May, booked 24 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday

Cheap flight deals from Chicago to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Portland (PDX). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated diciembre 18, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$192
(Kiwi.com)

One-way from

$108
(Delta)

Popular in

December

Cheapest in

September

Average price

$422
Provider with most accurate pricing for Chicago (CHI)-Portland flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Portland flights.
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From Chicago (CHI) to Portland
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One-way flight from Chicago (CHI) to Portland
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High demand for flights, 5% potential price rise
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Best time to find cheap flights, 2% potential price drop
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Average for round-trip flights in December 2024
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Find flight deals from Chicago to Portland

Cheapest flights from Chicago to Portland
Explore the most affordable flight options available from Chicago to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on diciembre 18, 2024.

This Frontier deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/256:00 amORD - PDX
1 stop11h 44mFrontier
mié. 1/112:45 pmPDX - ORD
1 stop9h 01mFrontier
Deal found 12/16$264
This FlightHub deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/198:34 pmORD - PDX
1 stop23h 45mMultiple Airlines
mar. 12/317:48 pmPDX - ORD
1 stop7h 42mMultiple Airlines
Deal found 12/16$272
This Cheapflightsfares deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/2510:00 amORD - PDX
1 stop9h 30mSun Country Air
lun. 12/3011:59 pmPDX - ORD
1 stop15h 39mSun Country Air
Deal found 12/17$348
This FlightHub deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/2310:04 pmMDW - PDX
1 stop19h 40mFrontier
dom. 12/2910:46 amPDX - MDW
1 stop16h 47mFrontier
Deal found 12/16$383
This Mytrip deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/319:35 pmORD - PDX
2 stops18h 14mSpirit Airlines
mar. 1/77:48 pmPDX - ORD
2 stops21h 00mSpirit Airlines
Deal found 12/17$391
This American Airlines deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/297:35 amORD - PDX
1 stop9h 34mAmerican Airlines
mié. 1/86:00 amPDX - ORD
1 stop9h 45mAmerican Airlines
Deal found 12/17$396
This Delta deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/257:30 amORD - PDX
1 stop7h 09mDelta
mar. 12/315:20 amPDX - ORD
1 stop5h 55mDelta
Deal found 12/17$418
This Alaska Airlines deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/257:00 amORD - PDX
Nonstop4h 38mAlaska Airlines
mar. 12/311:34 pmPDX - ORD
1 stop13h 06mAlaska Airlines
Deal found 12/17$485
This United Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/184:00 pmORD - PDX
Nonstop4h 41mUnited Airlines
lun. 1/611:55 pmPDX - ORD
Nonstop4h 01mUnited Airlines
Deal found 12/16$547
This Southwest deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/233:40 pmMDW - PDX
1 stop9h 45mSouthwest
mar. 12/3111:30 amPDX - MDW
Nonstop3h 55mSouthwest
Deal found 12/17$568
This Delta deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/172:15 pmMDW - PDX
1 stop8h 15mDelta
mar. 12/316:20 amPDX - MDW
1 stop8h 51mDelta
Deal found 12/16$612

Find flights from Chicago to Portland within your budget

Customize your flight search to find flights from Chicago to Portland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated diciembre 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

vie. 1/3

6:00 am-3:44 pm

1 stop11h 44m

Portland

mar. 1/7

7:48 pm-5:30 am

1 stop7h 42m

$192

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

mié. 1/22

8:15 am-12:07 am

1 stop17h 52m

Portland

mar. 3/18

10:06 am-12:17 am

1 stop12h 11m

$193

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

jue. 1/9

10:47 pm-9:21 am

1 stop12h 34m

Portland

mié. 1/15

5:30 pm-2:23 pm

2 stops18h 53m

$194

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

mié. 1/15

6:55 pm-9:41 pm

Nonstop4h 46m

Portland

mié. 1/22

7:00 am-1:07 pm

Nonstop4h 07m

$197

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

sáb. 3/8

6:54 pm-7:40 am

1 stop14h 46m

Portland

dom. 3/16

9:18 pm-5:04 am

1 stop29h 46m

$205

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

lun. 1/13

1:26 pm-8:35 pm

1 stop9h 09m

Portland

mar. 1/21

12:45 am-9:39 am

1 stop6h 54m

$208

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

lun. 1/13

2:25 pm-6:54 pm

1 stop6h 29m

Portland

jue. 1/23

6:05 am-3:30 pm

1 stop7h 25m

$208

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

jue. 1/16

8:10 pm-10:40 pm

Nonstop4h 30m

Portland

jue. 1/30

9:00 am-2:55 pm

Nonstop3h 55m

$218

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

mar. 5/6

8:20 pm-10:45 pm

Nonstop4h 25m

Portland

mar. 5/13

11:39 pm-5:45 am

Nonstop4h 06m

$227

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

sáb. 5/3

6:30 am-12:24 pm

1 stop7h 54m

Portland

sáb. 5/10

11:55 pm-5:39 am

Nonstop3h 44m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 26 results
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Compare providers for flights from Chicago to Portland

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Portland in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*1 star
KAYAKPrice Accuracy3 starsTrust Score*3 stars
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*2 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
FlightnetworkPrice Accuracy-Trust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Portland flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Portland flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Portland flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Portland flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Portland flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Chicago to Portland

Get recent, data-driven insights about flights from Chicago to Portland including ideal travel times, pricing trends, and more.

How far ahead should I book a flight from Chicago to Portland?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Portland. Price data was last updated on December 13, 2024.

To ensure you get the cheapest price possible for a flight from Chicago to Portland, you should look to book at least 24 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago to Portland?

Currently, November is the cheapest month in which you can book a flight from Chicago to Portland (average of $277). Flying from Chicago to Portland in March is currently the most expensive (average of $376). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to PDX?

Find hourly flight availability from Chicago to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated diciembre 18, 2024.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 46% on flights from Chicago to Portland by exploring options for tickets in the evening.

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

Use this chart to determine the cheapest time to fly round-trip from Chicago to Portland. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Portland flight should consider departing on Friday evenings when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Portland by month

Plan your trip to Portland by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Portland ranges from 0.7 - 5.6 inches per month. November is typically the wettest month, when rainfall can reach 5.6 in. July is typically the driest time to visit Portland when rainfall is around 0.7 in.

Temperature in Portland by month

Plan your trip to Portland by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Portland, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 41.0 F).

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Portland. Reviews last updated diciembre 18, 2024.
Read through reviews of airlines operating flights from Chicago to Portland, such as Spirit Airlines, Delta and Frontier. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Food

7.2

Entertainment

7.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Food

7.2

Entertainment

7.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,552 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Food

7.2

Entertainment

7.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Food

7.2

Entertainment

7.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
9,059 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Food

7.2

Entertainment

7.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Food

7.2

Entertainment

7.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • 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 5 inbound flights from Chicago per day. 7 airlines have flights to Portland from Chicago on a regular basis.

  • 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 $193 on this airline. Additional options worth looking into are Spirit Airlines and Alaska Airlines, starting at $194 and $197 round-trip. These flights start at 40% 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 Delta. According to our data, you can fly for as low as $108. Users have also found prices from $109 and $109 on Southwest and Alaska Airlines, respectively.

  • What are the most reliable airlines from Chicago to Portland?

    The top 3 most reliable airlines when flying from Chicago to Portland are Qatar Airways (94%), American Airlines (92%) and Air Canada (90%).

  • What are the cheapest flights from Chicago to Portland?

    Looking at all options, your cheapest flight can be booked for $133. While the most popular route (Chicago O'Hare Intl - Portland) can be booked for $127 on average our data indicates $626 when flying from Chicago to Portland.

  • Can I find deals for flights from Chicago to Portland that include hotel bookings?

    Yes. In addition to deals on Chicago to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Portland.

  • Can I find deals for business class flights from Chicago to Portland?

    Yes. Cheapflights offers flight deals from Chicago to Portland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Portland?

    Currently, November is the cheapest month in which you can book a flight from Chicago to Portland (average of $277). Flying from Chicago to Portland in March is currently the most expensive (average of $376). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Chicago to Portland

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Chicago to Portland

Discover the top 7 airlines that operate flights from Chicago to Portland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated diciembre 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$83Average$138FlexibilityNo cancel feeOn-time65%
FrontierCheapest$118Average$204FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$172Average$307FlexibilityNo cancel feeOn-time75%
DeltaCheapest$176Average$482FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$193Average$354FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$218Average$401FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$237Average$420FlexibilityNo cancel feeOn-time63%
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