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$154+ Cheap flights from Portland (PDX) to Chicago (CHI)

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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — CHI
Jul 11 — Jul 181
Sat 7/11
Sat 7/18
1 adult, Economy
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Find cheap flights from Portland to Chicago with Cheapflights

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Cheapflights Tip: The best prices from Portland to Chicago are usually found in January or February, booked 71 days in advance, depart on a Wednesday or Friday and return on a Tuesday

Cheap flight deals from Portland to Chicago

Cheapest flights from Portland to Chicago
Explore the most affordable flight options available from Portland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 11, 2026.

This Southwest deal was found by Cheapflights users on 6/7. 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.
Fri 8/76:20 am
PDX
-
MDW
2 stops8h 40m
Southwest
Mon 8/108:50 pm
MDW
-
PDX
Nonstop4h 15m
Southwest
Deal found 6/7$317
This Delta deal was found by Cheapflights users on 6/8. 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 8/2011:20 pm
PDX
-
ORD
1 stop6h 36m
Delta
Sun 8/237:00 am
ORD
-
PDX
1 stop6h 45m
Delta
Deal found 6/8$318
This Delta deal was found by Cheapflights users on 6/9. 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.
Mon 9/711:20 pm
PDX
-
MDW
1 stop7h 22m
Delta
Mon 9/1410:48 am
MDW
-
PDX
1 stop10h 11m
Delta
Deal found 6/9$318
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Wed 8/2611:34 pm
PDX
-
ORD
Nonstop3h 58m
American Airlines
Sun 8/306:00 am
ORD
-
PDX
1 stop8h 48m
American Airlines
Deal found 6/10$319
This Southwest deal was found by Cheapflights users on 6/10. 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 9/97:50 am
PDX
-
MDW
2 stops10h 00m
Southwest
Mon 9/146:15 am
MDW
-
PDX
2 stops10h 30m
Southwest
Deal found 6/10$319
This Alaska Airlines deal was found by Cheapflights users on 6/8. 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.
Tue 7/2810:59 pm
PDX
-
ORD
Nonstop4h 01m
Alaska Airlines
Sat 8/17:20 am
ORD
-
PDX
Nonstop4h 25m
Alaska Airlines
Deal found 6/8$320
This Southwest deal was found by Cheapflights users on 6/6. 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 7/711:30 pm
PDX
-
MDW
Nonstop3h 50m
Southwest
Tue 7/149:10 pm
MDW
-
PDX
Nonstop4h 25m
Southwest
Deal found 6/6$320
This Alaska Airlines deal was found by Cheapflights users on 6/10. 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 7/1810:59 pm
PDX
-
ORD
Nonstop4h 01m
Alaska Airlines
Sun 7/197:20 am
ORD
-
PDX
Nonstop4h 25m
Alaska Airlines
Deal found 6/10$321
This Delta deal was found by Cheapflights users on 6/10. 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.
Wed 8/512:35 am
PDX
-
MDW
1 stop6h 04m
Delta
Mon 8/107:25 pm
MDW
-
PDX
1 stop5h 55m
Delta
Deal found 6/10$321
This Travelocity deal was found by Cheapflights users on 6/10. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1710:59 pm
PDX
-
ORD
Nonstop4h 01m
Alaska Airlines
Fri 8/78:20 pm
ORD
-
PDX
1 stop13h 17m
Alaska Airlines
Deal found 6/10$322
This Southwest deal was found by Cheapflights users on 6/9. 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.
Fri 10/911:35 pm
PDX
-
MDW
Nonstop3h 50m
Southwest
Mon 10/129:50 pm
MDW
-
PDX
Nonstop4h 25m
Southwest
Deal found 6/9$322
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Tue 8/45:16 pm
PDX
-
ORD
2 stops12h 46m
Frontier
Mon 8/109:57 pm
ORD
-
PDX
1 stop20h 34m
Frontier
Deal found 6/10$323

Find flight deals from Portland to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to Chicago (CHI). 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 June 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$317
(Southwest)

One-way from

$154
(Delta)

Popular in

November

Cheapest in

January

Average price

$376

Good round-trip deal

$386 or less

Good one-way deal

$209 or less
Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Chicago (CHI) flights.
Search Deals
From Portland to Chicago (CHI)
Search Deals
One-way flight from Portland to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals
Price to beat on a round-trip flight from Portland to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Portland to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Chicago 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 June 11, 2026.
Use the filters below to find and compare flights from Portland to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 8/27

1:25 pm-11:48 pm

1 stop8h 23m

Chicago O'Hare Intl

Sun 8/30

7:00 am-11:45 am

1 stop6h 45m

$318

PortlandChicago

PDX - MDW

PDXMDW

Portland

Mon 8/3

8:15 pm-5:45 am

1 stop7h 30m

Chicago Midway

Thu 8/6

8:50 pm-11:05 pm

Nonstop4h 15m

$324

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 9/30

10:45 pm-8:55 am

1 stop8h 10m

Chicago Midway

Sat 10/3

7:20 pm-9:35 pm

Nonstop4h 15m

$325

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 7/22

11:30 pm-5:20 am

Nonstop3h 50m

Chicago Midway

Tue 7/28

6:40 pm-11:55 pm

1 stop7h 15m

$325

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 7/7

12:33 am-8:37 am

1 stop6h 04m

Chicago Midway

Wed 7/15

6:00 am-12:58 pm

1 stop8h 58m

$335

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 8/18

5:50 am-3:05 pm

1 stop7h 15m

Chicago Midway

Tue 8/18

4:45 pm-9:55 pm

1 stop7h 10m

$335

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 8/29

12:40 pm-8:45 pm

1 stop6h 05m

Chicago Midway

Mon 8/31

6:30 pm-8:45 pm

Nonstop4h 15m

$336

PortlandChicago

PDX - ORD

PDXORD

Portland

Mon 7/13

10:59 pm-5:00 am

Nonstop4h 01m

Chicago O'Hare Intl

Thu 7/16

7:20 am-9:45 am

Nonstop4h 25m

$337

PortlandChicago

PDX - ORD

PDXORD

Portland

Sun 7/26

10:59 pm-5:00 am

Nonstop4h 01m

Chicago O'Hare Intl

Thu 7/30

7:20 am-9:45 am

Nonstop4h 25m

$337

PortlandChicago

PDX - ORD

PDXORD

Portland

Mon 7/13

10:59 pm-5:00 am

Nonstop4h 01m

Chicago O'Hare Intl

Fri 7/17

7:20 am-9:45 am

Nonstop4h 25m

$337

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/8

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
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6

Compare providers for flights from Portland to Chicago

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 Portland to Chicago in June.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*1 star
PricelinePrice Accuracy1 starTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star

*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 Portland-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Portland-Chicago 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 Portland-Chicago 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 Portland to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Portland 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 Portland to Chicago

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

Currently, November is the cheapest month in which you can book a flight from Portland to Chicago (average of $103). Flying from Portland to Chicago in October is currently the most expensive (average of $783). 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 PDX to CHI?

Find hourly flight availability from Portland to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 11, 2026.

A simple way to save on the total cost of your ticket is to fly from Portland to Chicago in the afternoon. If you’re flexible enough to do this you can expect to save up to 14% on your trip compared to booking a flight in the morning.

Weekly flight availability from Portland to Chicago

Explore weekly flight availability from Portland to Chicago. 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 June 11, 2026.

The most flights from PDX to CHI are scheduled on a Wednesday (34 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (21 on average).

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

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

Booking 89 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Use this chart to determine the cheapest time to fly round-trip from Portland to Chicago. Price data was last updated on June 8, 2026.

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

The best insider tips for Portland to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Portland to Chicago trip
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Robert Schrader

Robert Schrader

Expert on Alaska Airlines

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
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

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 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

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated June 11, 2026.
Read reviews from past customers who have flown Alaska Airlines,Southwest, andDelta from Portland to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
7.9
Good
12,481 reviews

Comfort

7.8

Food

7.0

Boarding

8.1

Entertainment

7.0

Overall

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Jun 2026

SEA - RNO

There was a delay and my husband needs a wheelchair and we were moved from 1 gate to another.
Alaska Airlines
7.9
Good
12,481 reviews
Alaska Airlines
7.9
Good
12,481 reviews

Comfort

7.8

Food

7.0

Boarding

8.1

Entertainment

7.0

Overall

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Jun 2026

SEA - RNO

There was a delay and my husband needs a wheelchair and we were moved from 1 gate to another.
Southwest
7.9
Good
4,235 reviews
Alaska Airlines
7.9
Good
12,481 reviews

Comfort

7.8

Food

7.0

Boarding

8.1

Entertainment

7.0

Overall

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Jun 2026

SEA - RNO

There was a delay and my husband needs a wheelchair and we were moved from 1 gate to another.
Delta
7.9
Good
8,399 reviews
Alaska Airlines
7.9
Good
12,481 reviews

Comfort

7.8

Food

7.0

Boarding

8.1

Entertainment

7.0

Overall

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Jun 2026

SEA - RNO

There was a delay and my husband needs a wheelchair and we were moved from 1 gate to another.
United Airlines
7.4
Good
9,804 reviews
Alaska Airlines
7.9
Good
12,481 reviews

Comfort

7.8

Food

7.0

Boarding

8.1

Entertainment

7.0

Overall

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Jun 2026

SEA - RNO

There was a delay and my husband needs a wheelchair and we were moved from 1 gate to another.
American Airlines
7.1
Good
11,640 reviews
Alaska Airlines
7.9
Good
12,481 reviews

Comfort

7.8

Food

7.0

Boarding

8.1

Entertainment

7.0

Overall

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Jun 2026

SEA - RNO

There was a delay and my husband needs a wheelchair and we were moved from 1 gate to another.

Related info for your journey

Find useful and relevant information for your journey from Portland to Chicago. 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 from for flights from Portland to Chicago?

    For a flight from Portland to Chicago, you will be flying from Portland. Portland (PDX) is just 6.0 mi from the center of the city. Portland is the only Portland airport and it handles 26 outbound flights to Chicago per day. 7 airlines have flights to Chicago from Portland on a regular basis.

  • How long is the flight from Portland to Chicago?

    For as low as $337, Southwest can have you in Chicago from Portland in 4h 01m. Airlines will cover a distance of 1733 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Portland to Chicago round-trip?

    Hawaiian Airlines, at $93, was found to be the cheapest airline from Portland to Chicago.Alternate airlines to your destination round-trip include Frontier and Delta. You may be able to fly from Portland to Chicago for 72% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Portland to Chicago one-way?

    $72 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Hawaiian Airlines and Alaska Airlines, with prices starting from $98 and $107, respectively.

  • What are the most popular routes from Portland to Chicago?

    When deciding which route to take from Portland to Chicago consider Portland - Chicago O'Hare Intl, Portland - Chicago Midway or Portland - Chicago Greater Rockford as they are the most popular.

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

    Consider Qatar Airways (91%), Alaska Airlines (90%) or Malaysia Airlines (85%) when booking your flight. These represent the most reliable airlines when flying from Portland to Chicago.

  • What are the cheapest flights from Portland to Chicago?

    While on average a flight from Portland to Chicago is generally $1,027, our data shows the cheapest flight currently is $152. When looking at the most popular route, (Portland - Chicago O'Hare Intl), you can expect to pay $201 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Portland to Chicago 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 Portland to Chicago?

    Currently, November is the cheapest month in which you can book a flight from Portland to Chicago (average of $103). Flying from Portland to Chicago in October is currently the most expensive (average of $783). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Top 7 airlines flying from Portland to Chicago

Discover the top 7 airlines that operate flights from Portland to Chicago. 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 June 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$93Average$249FlexibilityNo cancel feeOn-time85%
FrontierCheapest$96Average$238FlexibilityNo cancel feeOn-time62%
DeltaCheapest$125Average$303FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$171Average$326FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$208Average$348FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$216Average$377FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$217Average$357FlexibilityNo cancel feeOn-time63%

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