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$100+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PDX
oct. 15 — oct. 221
mer. 10/15
mer. 10/22
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Portland are usually found in January or September, booked 60 days in advance, depart on a Wednesday or Tuesday and return on a Friday

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 septembre 15, 2025.

Round-trip from

$207
(Orbitz)

One-way from

$100
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$278

Good round-trip deal

$249 or less

Good one-way deal

$89 or less
From Chicago (CHI) to Portland
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One-way flight from Chicago (CHI) to Portland
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Highest demand for flights based on searches. 2% potential increase in price ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Portland.
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Price to beat on a 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 septembre 15, 2025.

This Orbitz deal was found by Cheapflights users on 9/13. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 10/257:05 amORD - PDX
1 stop6h 43mMultiple Airlines
mar. 10/287:00 amPDX - ORD
Nonstop4h 09mMultiple Airlines
Deal found 9/13$207
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 10/256:00 amORD - PDX
1 stop8h 25mHawaiian Airlines
ven. 10/3111:00 pmPDX - ORD
Nonstop4h 01mHawaiian Airlines
Deal found 9/13$208
This American Airlines deal was found by Cheapflights users on 9/14. 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.
sam. 10/257:30 amORD - PDX
Nonstop4h 29mAmerican Airlines
ven. 10/3111:58 pmPDX - ORD
Nonstop3h 55mAmerican Airlines
Deal found 9/14$210
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 10/187:00 amORD - PDX
Nonstop4h 32mMultiple Airlines
mar. 10/2112:43 pmPDX - ORD
1 stop9h 10mMultiple Airlines
Deal found 9/14$211
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 10/297:20 amORD - PDX
2 stops57h 11mFrontier
sam. 11/112:52 pmPDX - ORD
1 stop9h 20mFrontier
Deal found 9/15$212
This Frontier deal was found by Cheapflights users on 9/13. 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.
jeu. 10/236:50 amORD - PDX
1 stop6h 48mFrontier
dim. 10/2612:43 pmPDX - ORD
1 stop9h 10mFrontier
Deal found 9/13$213
This Lucky2Go deal was found by Cheapflights users on 9/14. 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 Lucky2Go is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 10/258:00 amORD - PDX
1 stop7h 43mAlaska Airlines
ven. 10/3111:00 pmPDX - ORD
Nonstop4h 01mAlaska Airlines
Deal found 9/14$214
This United Airlines deal was found by Cheapflights users on 9/14. 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.
sam. 10/253:47 pmORD - PDX
1 stop8h 58mUnited Airlines
ven. 10/3111:59 pmPDX - ORD
Nonstop3h 53mUnited Airlines
Deal found 9/14$215
This Expedia deal was found by Cheapflights users on 9/13. 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.
mer. 10/292:05 pmORD - PDX
Nonstop4h 36mMultiple Airlines
sam. 11/112:52 pmPDX - ORD
1 stop9h 20mMultiple Airlines
Deal found 9/13$216
This United Airlines deal was found by Cheapflights users on 9/12. 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.
mer. 10/87:50 pmORD - PDX
Nonstop4h 35mUnited Airlines
dim. 10/1211:59 pmPDX - ORD
Nonstop4h 01mUnited Airlines
Deal found 9/12$217
This Trip.com deal was found by Cheapflights users on 9/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 10/246:50 amORD - PDX
1 stop6h 58mMultiple Airlines
jeu. 10/3011:00 pmPDX - ORD
Nonstop4h 01mMultiple Airlines
Deal found 9/14$218
This Southwest deal was found by Cheapflights users on 9/13. 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.
sam. 10/253:45 pmMDW - PDX
Nonstop4h 20mSouthwest
ven. 10/3110:15 amPDX - MDW
1 stop7h 45mSouthwest
Deal found 9/13$219

Cheapflights Fare Finder

 
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 septembre 15, 2025.
Use the filters below to find and compare flights from Chicago to Portland that are best for you.

Fly from

Chicago

Fly to

Portland

Route

Depart

Return

Price

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

mar. 10/21

7:59 pm-9:44 am

1 stop15h 45m

Portland

mer. 10/29

11:00 pm-5:01 am

Nonstop4h 01m

$208

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

sam. 10/25

7:00 am-9:32 am

Nonstop4h 32m

Portland

ven. 10/31

11:00 pm-5:01 am

Nonstop4h 01m

$209

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

sam. 10/25

7:00 am-9:32 am

Nonstop4h 32m

Portland

ven. 10/31

11:00 pm-5:01 am

Nonstop4h 01m

$209

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

lun. 11/24

7:00 am-9:39 am

Nonstop4h 39m

Portland

ven. 11/28

11:00 pm-5:01 am

Nonstop4h 01m

$222

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

sam. 10/25

3:45 pm-6:05 pm

Nonstop4h 20m

Portland

ven. 10/31

6:00 am-6:05 pm

1 stop10h 05m

$224

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

mar. 10/14

9:05 am-11:41 am

Nonstop4h 36m

Portland

mar. 10/21

11:59 pm-6:00 am

Nonstop4h 01m

$231

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

mar. 10/7

8:05 pm-10:40 pm

Nonstop4h 35m

Portland

mar. 10/14

2:15 pm-8:25 pm

Nonstop4h 10m

$231

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

mer. 11/12

2:05 pm-4:41 pm

Nonstop4h 36m

Portland

sam. 11/15

11:00 pm-5:01 am

Nonstop4h 01m

$231

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

mar. 10/21

7:50 pm-10:25 pm

Nonstop4h 35m

Portland

mer. 10/29

11:59 pm-5:54 am

Nonstop3h 55m

$231

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

mar. 10/7

2:04 pm-4:37 pm

Nonstop4h 33m

Portland

dim. 10/12

11:00 pm-5:01 am

Nonstop4h 01m

$233

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 38 results
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The best insider tips for Chicago to Portland flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Chicago to Portland trip
Airlines
Alaska Airlines

Alaska's Premium Class offers extra legroom and free cocktails, ideal for a comfortable flight.


Alaska Airlines' Wi-Fi is a bargain, perfect for getting work done on longer flights.

Read more about Alaska Airlinesby Robert Schrader
Spirit Airlines

Spirit's Big Front Seats offer 11 inches more legroom, perfect for working with a laptop.


Spirit's Economy Plus Bundle includes both carry-on and check-in bags, saving on extra fees.

Read more about Spirit Airlinesby Daniel Scheffler
Airports
ORD

Avoid long walks at ORD by using the free shuttle train between terminals outside of security.

Read more about ORDby Ramsey Qubein
MDW

Order food via the airport’s mobile system directly to your gate to save time and ensure you don't miss boarding.

Read more about MDWby Ramsey Qubein
PDX

Use the MAX light rail for a convenient 40-minute ride between PDX and Downtown Portland.

Read more about PDXby Brandon Schultz
Our travel experts
Robert Schrader

Robert Schrader

Expert on Alaska Airlines

Robert Schrader

Robert Schrader

One of the web's original travel bloggers, Robert launched his first site Leave Your Daily Hell in 2009. Since then, he's expanded into destination niche sites (one each for Japan, Thailand and Taiwan), in addition to having written for the inflight magazines of Singapore Airlines and Korean Air. Overall, he's visited nearly 100 countries, and flies business as often as possible.

Read more
Daniel Scheffler

Daniel Scheffler

Expert on Spirit Airlines

Daniel Scheffler

Daniel Scheffler

Daniel Scheffler is a travel writer, podcaster, and producer. Born in Africa, bred in Europe and now living in America he has traveled to 140 countries (and all 50 U.S. states). Plus he has stayed at over 2500 hotels across the globe. His original shows Everywhere and Without Maps (available on Spotify) showcase his beliefs, travel is about humanity and sharing that beauty. And thus it reminds you that you shouldn’t believe everything you think.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Brandon Schultz

Brandon Schultz

Expert on PDX

Brandon Schultz

Brandon Schultz

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more

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.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Portland

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 September 12, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Portland, you should look to book at least 60 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 $368). 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 septembre 15, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 28% 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 September 14, 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 septembre 15, 2025.

The most flights from CHI to PDX are scheduled on a Friday (29 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (20 on average).

How much does it cost to fly round-trip from Chicago to Portland?

What’s the top layover airport for flights from Chicago to Portland?

Share of 1-stop round-trip flights from Chicago to Portland chosen by Cheapflights users in the past 12 months, using the same layover each way.

Las Vegas (LAS) – chosen by Cheapflights users on 97% of 1-stop itineraries from Chicago to Portland on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to Portland?

Average round-trip fare for 1-stop flights from Chicago to Portland, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Denver (DEN) is the most affordable 1-stop option, with an average round-trip price of $138.

What’s the fastest layover option from Chicago to Portland?

Shortest average travel time for 1-stop one-way flights from Chicago to Portland, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Denver (DEN) have the shortest average one-way travel time for 1-stop routes: 7h 58m.

Which airport typically offers the quickest layover for flights from Chicago to Portland?

Average layover duration for 1-stop one-way flights from Chicago to Portland, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Denver (DEN) offer the fastest connection on this route, with an average layover time of 5h 46m.

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 septembre 15, 2025.
Read through reviews of airlines operating flights from Chicago to Portland, such as Alaska Airlines, Southwest, and Hawaiian Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Southwest
8.0
Very good
4,242 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Hawaiian Airlines
7.8
Good
2,723 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,929 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Food

7.1

Entertainment

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

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 25 inbound flights from Chicago per day. 8 airlines have flights to Portland from Chicago on a regular basis.

  • How long is the flight from Chicago to Portland?

    Airlines like Alaska Airlines, Hawaiian Airlines, and Southwest fly from Chicago to Portland in about 4h 20m. The time it takes to get you to your destination can typically vary by up to 11h 25m. Airlines will cover a distance of 1746 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 Spirit Airlines. Our recent data shows that you can find tickets from as low as $86 on this airline. Additional options worth looking into are Frontier and Delta, starting at $108 and $123 round-trip. These flights start at 73% 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 United Airlines. According to our data, you can fly for as low as $109. Users have also found prices from $109 and $116 on Delta 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 United Airlines (81%), Brussels Airlines (75%) and Air Canada (74%).

  • What are the cheapest flights from Chicago to Portland?

    Looking at all options, your cheapest flight can be booked for $89. While the most popular route (Chicago O'Hare Intl - Portland) can be booked for $165 on average, our data indicates $729 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 $368). 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 Portland?

Book flights to Portland if you plan to visit one of these locations
Vancouver
Seaside
Beaverton
Clackamas
McMinnville
Lake Oswego
Hillsboro
Cannon Beach
Long Beach
Longview
Lincoln City
Tigard
Depoe Bay
Stevenson
Wilsonville
Pacific City
Tillamook
Troutdale
Gresham
Silverton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 8 airlines flying from Chicago to Portland

Discover the top 8 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 septembre 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$86Average$184FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$179FlexibilityNo cancel feeOn-time62%
DeltaCheapest$123Average$328FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$134Average$284FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$183Average$289FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$213Average$317FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$227Average$383FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$238Average$453FlexibilityNo cancel feeOn-time63%

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