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$91+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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The best prices from Chicago to Portland are usually found in September or August, booked 24 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday

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 November 21, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

March

Cheapest in

September

Round-trip from

$180
(FlightHub)

One-way from

$91
(FlightHub)
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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High demand for flights, 19% potential price rise
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Best time to find cheap flights, 16% potential price drop
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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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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 November 21, 2024.

This FlightHub deal was found by Cheapflights users on 11/20. 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.
Fri 12/206:00 amORD - PDX
1 stop11h 44mFrontier
Mon 12/231:05 pmPDX - ORD
1 stop8h 41mFrontier
Deal found 11/20$180
This Expedia deal was found by Cheapflights users on 11/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/101:58 pmORD - PDX
Nonstop4h 31mMultiple Airlines
Fri 12/135:00 amPDX - ORD
1 stop7h 26mMultiple Airlines
Deal found 11/19$183
This FlightHub deal was found by Cheapflights users on 11/21. 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.
Mon 12/93:21 pmORD - PDX
1 stop10h 27mSpirit Airlines
Tue 12/107:16 pmPDX - ORD
1 stop8h 14mSpirit Airlines
Deal found 11/21$185
This CheapOair deal was found by Cheapflights users on 11/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1612:43 pmMDW - PDX
1 stop25h 51mFrontier
Wed 12/1812:45 pmPDX - MDW
1 stop6h 47mFrontier
Deal found 11/21$198
This United Airlines deal was found by Cheapflights users on 11/20. 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.
Wed 12/114:00 pmORD - PDX
Nonstop4h 41mUnited Airlines
Sat 12/141:20 pmPDX - ORD
1 stop7h 52mUnited Airlines
Deal found 11/20$207
This Alaska Airlines deal was found by Cheapflights users on 11/21. 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.
Thu 12/126:32 amORD - PDX
1 stop18h 23mAlaska Airlines
Sun 12/157:00 amPDX - ORD
Nonstop4h 02mAlaska Airlines
Deal found 11/21$249
This Sun Country Air deal was found by Cheapflights users on 11/21. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2410:00 amORD - PDX
1 stop9h 30mSun Country Air
Thu 1/25:57 pmPDX - ORD
1 stop15h 00mSun Country Air
Deal found 11/21$265
This Southwest deal was found by Cheapflights users on 11/20. 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.
Wed 12/117:40 pmMDW - PDX
Nonstop4h 30mSouthwest
Sat 12/146:35 amPDX - MDW
Nonstop3h 55mSouthwest
Deal found 11/20$283
This Delta deal was found by Cheapflights users on 11/21. 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.
Thu 11/2811:59 amMDW - PDX
1 stop6h 18mDelta
Thu 11/2812:59 amPDX - MDW
1 stop5h 52mDelta
Deal found 11/21$293
This eDestinos deal was found by Cheapflights users on 11/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/198:41 pmMDW - PDX
1 stop23h 41mMultiple Airlines
Thu 12/267:19 pmPDX - MDW
2 stops22h 15mMultiple Airlines
Deal found 11/19$334
This Delta deal was found by Cheapflights users on 11/21. 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.
Sun 12/222:10 pmORD - PDX
1 stop9h 03mDelta
Mon 12/305:20 amPDX - ORD
1 stop5h 55mDelta
Deal found 11/21$348

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 2,612,795 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 12/20

6:00 am-3:44 pm

1 stop11h 44m

Portland

Mon 12/23

1:05 pm-11:46 pm

1 stop8h 41m

$180

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 12/10

1:58 pm-4:29 pm

Nonstop4h 31m

Portland

Fri 12/13

5:00 am-2:26 pm

1 stop7h 26m

$183

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Mon 12/9

3:21 pm-11:48 pm

1 stop10h 27m

Portland

Tue 12/10

7:16 pm-5:30 am

1 stop8h 14m

$185

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 2/18

4:05 pm-6:44 pm

Nonstop4h 39m

Portland

Wed 2/19

7:00 am-1:04 pm

Nonstop4h 04m

$197

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Mon 12/16

12:43 pm-12:34 pm

1 stop25h 51m

Portland

Wed 12/18

12:45 pm-9:32 pm

1 stop6h 47m

$198

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 1/18

2:39 pm-9:00 pm

1 stop8h 21m

Portland

Tue 1/21

7:00 am-1:01 pm

Nonstop4h 01m

$207

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 1/15

6:15 am-12:55 pm

1 stop8h 40m

Portland

Wed 1/22

10:16 am-6:23 pm

1 stop6h 07m

$216

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 2/18

1:26 pm-8:36 pm

1 stop9h 10m

Portland

Fri 2/21

12:45 am-10:36 am

1 stop7h 51m

$226

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 2/18

8:10 pm-10:40 pm

Nonstop4h 30m

Portland

Sat 2/22

6:35 am-12:30 pm

Nonstop3h 55m

$264

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 12/24

10:00 am-5:30 pm

1 stop9h 30m

Portland

Thu 1/2

5:57 pm-10:57 am

1 stop15h 00m

$265

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/21

Showing 1-10 of 24 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 November.
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 Accuracy1 starTrust Score*3 stars
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
FlightnetworkPrice Accuracy-Trust Score*3 stars
Trip.comPrice Accuracy2 starsTrust 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 November 15, 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 $268). Flying from Chicago to Portland in July is currently the most expensive (average of $341). 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 November 21, 2024.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 47% 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 November 18, 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.

Weekly flight availability from Chicago to Portland

Explore weekly flight availability from Chicago to Portland. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated November 21, 2024.

The most flights from CHI to PDX are scheduled on a Thursday (17 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 on average).

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 November 21, 2024.
Read through reviews of airlines operating flights from Chicago to Portland, such as Frontier, Spirit Airlines and Alaska Airlines. 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
5,005 reviews

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,005 reviews
Southwest
8.1
Very good
5,005 reviews

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,464 reviews
Southwest
8.1
Very good
5,005 reviews

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,755 reviews
Southwest
8.1
Very good
5,005 reviews

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,172 reviews
Southwest
8.1
Very good
5,005 reviews

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Sun Country Air
7.0
Good
415 reviews
Southwest
8.1
Very good
5,005 reviews

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 10 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 $180 on this airline. Additional options worth looking into are Spirit Airlines and Alaska Airlines, starting at $185 and $197 round-trip. These flights start at 44% 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 Spirit Airlines. According to our data, you can fly for as low as $91. Users have also found prices from $93 and $99 on Frontier and Southwest, 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%), Hawaiian Airlines (92%) and Alaska Airlines (90%).

  • What are the cheapest flights from Chicago to Portland?

    Looking at all options, your cheapest flight can be booked for $98. While the most popular route (Chicago O'Hare Intl - Portland) can be booked for $145 on average our data indicates $590 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 $268). Flying from Chicago to Portland in July is currently the most expensive (average of $341). 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.

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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 2,612,795 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$83Average$139FlexibilityNo cancel feeOn-time65%
FrontierCheapest$118Average$202FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$172Average$313FlexibilityNo cancel feeOn-time75%
DeltaCheapest$176Average$482FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$193Average$355FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$218Average$402FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$237Average$420FlexibilityNo cancel feeOn-time63%
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