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$94+ 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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
Feb 26 — Mar 51
Wed 2/26
Wed 3/5
1 adult, Economy
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The best prices from Chicago to Portland are usually found in September or January, 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 February 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$221
(Frontier)

One-way from

$94
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$333

Good round-trip deal

$288 or less

Good one-way deal

$118 or less
Provider with most accurate pricing for Chicago (CHI)-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Portland flights.
Search Deals
From Chicago (CHI) to Portland
Search Deals
One-way flight from Chicago (CHI) to Portland
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Portland.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Portland.
Search Deals

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 February 21, 2025.

This Frontier deal was found by Cheapflights users on 2/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/188:36 pmMDW - PDX
1 stop14h 20mFrontier
Mon 4/219:01 amPDX - MDW
1 stop10h 59mFrontier
Deal found 2/20$221
This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/66:15 amORD - PDX
3 stops38h 22mSpirit Airlines
Mon 3/102:33 pmPDX - ORD
1 stop14h 09mSpirit Airlines
Deal found 2/20$221
This United Airlines deal was found by Cheapflights users on 2/20. 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.
Sat 4/54:12 pmORD - PDX
Nonstop4h 33mUnited Airlines
Sat 4/122:25 pmPDX - ORD
1 stop7h 50mUnited Airlines
Deal found 2/20$224
This American Airlines deal was found by Cheapflights users on 2/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/128:20 pmORD - PDX
Nonstop4h 42mAmerican Airlines
Wed 4/1611:52 pmPDX - ORD
Nonstop4h 05mAmerican Airlines
Deal found 2/21$227
This Delta deal was found by Cheapflights users on 2/21. 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.
Sat 4/51:26 pmORD - PDX
2 stops9h 22mDelta
Fri 4/1112:59 amPDX - ORD
1 stop7h 26mDelta
Deal found 2/21$231
This Expedia deal was found by Cheapflights users on 2/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/183:16 pmORD - PDX
Nonstop4h 34mMultiple Airlines
Sun 4/207:01 pmPDX - ORD
1 stop9h 32mMultiple Airlines
Deal found 2/20$232
This Alaska Airlines deal was found by Cheapflights users on 2/20. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/192:04 pmORD - PDX
Nonstop4h 32mAlaska Airlines
Tue 4/298:45 pmPDX - ORD
1 stop7h 20mAlaska Airlines
Deal found 2/20$237
This Southwest deal was found by Cheapflights users on 2/20. 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.
Tue 4/84:55 pmMDW - PDX
1 stop7h 20mSouthwest
Mon 4/146:55 pmPDX - MDW
1 stop8h 25mSouthwest
Deal found 2/20$247
This Hawaiian Airlines deal was found by Cheapflights users on 2/20. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/43:16 pmORD - PDX
Nonstop4h 34mHawaiian Airlines
Wed 4/91:25 pmPDX - ORD
1 stop8h 34mHawaiian Airlines
Deal found 2/20$247
This Delta deal was found by Cheapflights users on 2/21. 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.
Sat 4/51:12 pmMDW - PDX
2 stops9h 36mDelta
Sat 4/127:29 pmPDX - MDW
2 stops11h 14mDelta
Deal found 2/21$254
This Booking.com deal was found by Cheapflights users on 2/21. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/17:59 pmORD - PDX
1 stop14h 41mFrontier
Sun 3/29:18 pmPDX - ORD
1 stop29h 42mFrontier
Deal found 2/21$277
This Sun Country Air deal was found by Cheapflights users on 2/21. 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.
Thu 8/78:10 pmORD - PDX
1 stop23h 36mSun Country Air
Sun 8/1011:59 pmPDX - ORD
1 stop17h 12mSun Country Air
Deal found 2/21$310

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 February 21, 2025.

Fly from

Chicago

Fly to

Portland

Route

Depart

Return

Price

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 4/18

8:36 pm-8:56 am

1 stop14h 20m

Portland

Mon 4/21

9:01 am-10:00 pm

1 stop10h 59m

$221

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 3/6

6:15 am-6:37 pm

3 stops38h 22m

Portland

Mon 3/10

2:33 pm-6:42 am

1 stop14h 09m

$221

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 4/5

4:12 pm-6:45 pm

Nonstop4h 33m

Portland

Sat 4/12

2:25 pm-12:15 am

1 stop7h 50m

$224

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 4/12

8:20 pm-11:02 pm

Nonstop4h 42m

Portland

Wed 4/16

11:52 pm-5:57 am

Nonstop4h 05m

$227

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 4/5

1:26 pm-8:48 pm

2 stops9h 22m

Portland

Fri 4/11

12:59 am-10:25 am

1 stop7h 26m

$231

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 4/18

3:16 pm-5:50 pm

Nonstop4h 34m

Portland

Sun 4/20

7:01 pm-6:33 am

1 stop9h 32m

$232

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 4/19

2:04 pm-4:36 pm

Nonstop4h 32m

Portland

Tue 4/29

8:45 pm-6:05 am

1 stop7h 20m

$237

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 4/8

4:55 pm-10:15 pm

1 stop7h 20m

Portland

Mon 4/14

6:55 pm-5:20 am

1 stop8h 25m

$247

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 4/4

3:16 pm-5:50 pm

Nonstop4h 34m

Portland

Wed 4/9

1:25 pm-11:59 pm

1 stop8h 34m

$247

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 4/5

1:12 pm-8:48 pm

2 stops9h 36m

Portland

Sat 4/12

7:29 pm-8:43 am

2 stops11h 14m

$254

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/21

Showing 1-10 of 28 results
1
2
3

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*1 star
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
FlightnetworkPrice Accuracy-Trust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*2 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 February 14, 2025.

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 February 21, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 43% 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 February 16, 2025.

Travelers seeking maximum savings on their Chicago to Portland flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday at noon 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 February 21, 2025.

The most flights from CHI to PDX are scheduled on a Thursday (16 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 February 21, 2025.
Read through reviews of airlines operating flights from Chicago to Portland, such as Southwest, Alaska Airlines and Delta. 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
4,408 reviews

Entertainment

7.6

Food

7.1

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,408 reviews
Southwest
8.1
Very good
4,408 reviews

Entertainment

7.6

Food

7.1

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,697 reviews
Southwest
8.1
Very good
4,408 reviews

Entertainment

7.6

Food

7.1

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,217 reviews
Southwest
8.1
Very good
4,408 reviews

Entertainment

7.6

Food

7.1

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Hawaiian Airlines
7.9
Good
2,317 reviews
Southwest
8.1
Very good
4,408 reviews

Entertainment

7.6

Food

7.1

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,760 reviews
Southwest
8.1
Very good
4,408 reviews

Entertainment

7.6

Food

7.1

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 12 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 $221 on this airline. Additional options worth looking into are Spirit Airlines and United Airlines, starting at $221 and $224 round-trip. These flights start at 31% 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 $94. Users have also found prices from $95 and $97 on Spirit Airlines and Delta, respectively.

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

    The top 3 most reliable airlines when flying from Chicago to Portland are Brussels Airlines (97%), Iberia (92%) and Lufthansa (85%).

  • What are the cheapest flights from Chicago to Portland?

    Looking at all options, your cheapest flight can be booked for $113. While the most popular route (Chicago O'Hare Intl - Portland) can be booked for $127 on average our data indicates $770 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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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 February 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$83Average$139FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$209FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$173Average$296FlexibilityNo cancel feeOn-time75%
DeltaCheapest$176Average$366FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$195Average$338FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$217Average$394FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$228Average$431FlexibilityNo cancel feeOn-time63%
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