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$80+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — CHI
feb. 24 — mar. 31
lun. 2/24
lun. 3/3
1 adult, Economy
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Find cheap flights from Portland to Chicago with Cheapflights

1. Tell us where you want to go
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The best prices from Portland to Chicago are usually found in January or August, booked 48 days in advance, depart on a Wednesday or Thursday and return on a Wednesday

Cheap 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 febrero 19, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$230
(Frontier)

One-way from

$80
(Mytrip)

Popular in

March

Cheapest in

January

Average price

$346

Good round-trip deal

$394 or less

Good one-way deal

$201 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. 6% potential increase in price ($23 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 Portland to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Portland to Chicago (CHI).
Search Deals

Find 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 febrero 19, 2025.

This Expedia deal was found by Cheapflights users on 2/19. 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.
mié. 4/93:22 pmPDX - ORD
1 stop7h 41mMultiple Airlines
lun. 4/143:16 pmORD - PDX
Nonstop4h 34mMultiple Airlines
Deal found 2/19$234
This Mytrip deal was found by Cheapflights users on 2/18. 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.
mié. 3/57:32 pmPDX - ORD
1 stop9h 10mSpirit Airlines
dom. 3/233:16 pmORD - PDX
2 stops23h 09mSpirit Airlines
Deal found 2/18$235
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/2212:50 amPDX - ORD
1 stop5h 45mDelta
mar. 4/296:25 pmORD - PDX
1 stop7h 31mDelta
Deal found 2/19$237
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/2310:59 pmPDX - MDW
1 stop7h 41mDelta
mar. 4/291:16 pmMDW - PDX
1 stop9h 23mDelta
Deal found 2/19$237
This American Airlines deal was found by Cheapflights users on 2/18. 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.
vie. 6/611:55 pmPDX - ORD
Nonstop4h 05mAmerican Airlines
mié. 6/118:15 pmORD - PDX
Nonstop4h 28mAmerican Airlines
Deal found 2/18$238
This CheapOair deal was found by Cheapflights users on 2/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/36:32 amPDX - MDW
1 stop15h 45mFrontier
vie. 3/78:44 pmMDW - PDX
1 stop13h 56mFrontier
Deal found 2/19$240
This United Airlines deal was found by Cheapflights users on 2/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/1911:58 pmPDX - ORD
Nonstop3h 57mUnited Airlines
mié. 3/267:59 pmORD - PDX
Nonstop4h 40mUnited Airlines
Deal found 2/19$245
This Alaska Airlines deal was found by Cheapflights users on 2/19. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/19:30 pmPDX - ORD
1 stop12h 34mAlaska Airlines
mar. 9/307:00 amORD - PDX
Nonstop4h 34mAlaska Airlines
Deal found 2/19$248
This Hawaiian Airlines deal was found by Cheapflights users on 2/19. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/117:00 amPDX - ORD
Nonstop4h 04mHawaiian Airlines
dom. 10/127:00 amORD - PDX
Nonstop4h 34mHawaiian Airlines
Deal found 2/19$253
This Southwest deal was found by Cheapflights users on 2/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 4/126:45 amPDX - MDW
Nonstop4h 00mSouthwest
vie. 4/184:15 pmMDW - PDX
Nonstop4h 20mSouthwest
Deal found 2/19$272
This CheapOair deal was found by Cheapflights users on 2/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/276:32 amPDX - ORD
1 stop15h 51mFrontier
jue. 4/107:39 pmORD - PDX
1 stop15h 08mFrontier
Deal found 2/19$276
This Sun Country Air deal was found by Cheapflights users on 2/19. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 7/126:45 pmPDX - ORD
1 stop22h 26mSun Country Air
jue. 7/178:10 pmORD - PDX
1 stop28h 36mSun Country Air
Deal found 2/19$305

Find flights from Portland to Chicago within your budget

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 febrero 19, 2025.

Fly from

Portland

Fly to

Chicago

Route

Depart

Return

Price

PortlandChicago

PDX - ORD

PDXORD

Portland

mié. 4/9

3:22 pm-1:03 am

1 stop7h 41m

Chicago O'Hare Intl

lun. 4/14

3:16 pm-5:50 pm

Nonstop4h 34m

$234

PortlandChicago

PDX - ORD

PDXORD

Portland

mié. 3/5

7:32 pm-6:42 am

1 stop9h 10m

Chicago O'Hare Intl

dom. 3/23

3:16 pm-12:25 pm

2 stops23h 09m

$235

PortlandChicago

PDX - ORD

PDXORD

Portland

mar. 4/22

12:50 am-8:35 am

1 stop5h 45m

Chicago O'Hare Intl

mar. 4/29

6:25 pm-11:56 pm

1 stop7h 31m

$237

PortlandChicago

PDX - MDW

PDXMDW

Portland

mié. 4/23

10:59 pm-8:40 am

1 stop7h 41m

Chicago Midway

mar. 4/29

1:16 pm-8:39 pm

1 stop9h 23m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

vie. 6/6

11:55 pm-6:00 am

Nonstop4h 05m

Chicago O'Hare Intl

mié. 6/11

8:15 pm-10:43 pm

Nonstop4h 28m

$238

PortlandChicago

PDX - MDW

PDXMDW

Portland

lun. 3/3

6:32 am-12:17 am

1 stop15h 45m

Chicago Midway

vie. 3/7

8:44 pm-8:40 am

1 stop13h 56m

$240

PortlandChicago

PDX - ORD

PDXORD

Portland

mié. 3/19

11:58 pm-5:55 am

Nonstop3h 57m

Chicago O'Hare Intl

mié. 3/26

7:59 pm-10:39 pm

Nonstop4h 40m

$245

PortlandChicago

PDX - ORD

PDXORD

Portland

vie. 6/6

5:51 pm-11:56 pm

Nonstop4h 05m

Chicago O'Hare Intl

mié. 6/11

7:59 pm-9:47 am

1 stop15h 48m

$268

PortlandChicago

PDX - MDW

PDXMDW

Portland

sáb. 4/12

6:45 am-12:45 pm

Nonstop4h 00m

Chicago Midway

vie. 4/18

4:15 pm-6:35 pm

Nonstop4h 20m

$272

PortlandChicago

PDX - ORD

PDXORD

Portland

jue. 3/27

6:32 am-12:23 am

1 stop15h 51m

Chicago O'Hare Intl

jue. 4/10

7:39 pm-8:47 am

1 stop15h 08m

$276

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 30 results
1
2
3

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
CheapfaremartPrice Accuracy-Trust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*2 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy1 starTrust Score*3 stars
FlightnetworkPrice Accuracy-Trust Score*3 stars

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

  • Most accurate provider: When it comes to deals on 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.

Travel insights for flights from Portland to Chicago

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

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

Use this chart to determine the optimal time to book a round-trip flight from Portland to Chicago. Price data was last updated on February 14, 2025.

Booking 48 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 month to book a flight from Portland to Chicago?

Currently, August is the cheapest month in which you can book a flight from Portland to Chicago (average of $245). Flying from Portland to Chicago in March is currently the most expensive (average of $321). 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 febrero 19, 2025.

A simple way to save on the total cost of your ticket is to fly from Portland to Chicago in the evening. If you’re flexible enough to do this you can expect to save up to 28% on your trip compared to booking a flight in the morning.

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 February 16, 2025.

Travelers seeking maximum savings on their Portland to Chicago flight should consider departing on Saturday afternoons 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.

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 febrero 19, 2025.

The most flights from PDX to CHI are scheduled on a Monday (15 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 Chicago by month

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

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

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

If weather is an important factor for your trip to Chicago, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 febrero 19, 2025.
See what other customers who have flown with Southwest, Alaska Airlines and Delta from Portland to Chicago have to say. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,413 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

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
4,413 reviews
Southwest
8.1
Very good
4,413 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

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
9,691 reviews
Southwest
8.1
Very good
4,413 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

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
8,236 reviews
Southwest
8.1
Very good
4,413 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

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
4,413 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

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
8,771 reviews
Southwest
8.1
Very good
4,413 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.6

Overall

8.1

Boarding

8.2

Food

7.1

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 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 12 outbound flights to Chicago per day. 7 airlines have flights to Chicago from Portland on a regular basis.

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

    Frontier, at $230, was found to be the cheapest airline from Portland to Chicago.Alternate airlines to your destination round-trip include Spirit Airlines and Delta. You may be able to fly from Portland to Chicago for 32% less than the average price by searching for these airlines.

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

    $80 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Frontier and United Airlines, with prices starting from $81 and $114, 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 Brussels Airlines (97%), SWISS (97%) or Lufthansa (95%) 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 $1,013, our data shows the cheapest flight currently is $127. When looking at the most popular route, (Portland - Chicago O'Hare Intl), you can expect to pay $122 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, August is the cheapest month in which you can book a flight from Portland to Chicago (average of $245). Flying from Portland to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for Portland to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Portland to O'Hare Intl flights
Portland to Midway flights
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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 febrero 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$82Average$135FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$240FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$178Average$341FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$189Average$342FlexibilityNo cancel feeOn-time71%
DeltaCheapest$207Average$384FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$218Average$409FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$246Average$396FlexibilityNo cancel feeOn-time63%
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