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$109+ 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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — CHI
Jan 22 — Jan 291
Wed 1/22
Wed 1/29
1 adult, Economy
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1. Tell us where you want to go
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The best prices from Portland to Chicago are usually found in February or August, booked 79 days in advance, depart on a Tuesday or Wednesday 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 January 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$227
(American Airlines)

One-way from

$109
(Mytrip)

Popular in

March

Cheapest in

February

Average price

$316
Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Portland-Chicago (CHI) flights.
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From Portland to Chicago (CHI)
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One-way flight from Portland to Chicago (CHI)
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High demand for flights, 3% potential price rise
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Best time to find cheap flights, 2% potential price drop
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Average for round-trip flights in January 2025
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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 January 17, 2025.

This Alaska Airlines deal was found by Cheapflights users on 1/16. 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 9/1311:00 pmPDX - ORD
Nonstop4h 04mAlaska Airlines
Wed 9/177:00 amORD - PDX
Nonstop4h 34mAlaska Airlines
Deal found 1/16$227
This FlightHub deal was found by Cheapflights users on 1/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/3112:03 pmPDX - ORD
1 stop10h 29mMultiple Airlines
Mon 2/310:47 pmORD - PDX
1 stop19h 48mMultiple Airlines
Deal found 1/15$228
This Booking.com deal was found by Cheapflights users on 1/16. 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.
Sun 1/2612:03 pmPDX - ORD
1 stop24h 08mFrontier
Thu 1/306:36 pmORD - PDX
1 stop17h 09mFrontier
Deal found 1/16$230
This Booking.com deal was found by Cheapflights users on 1/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/2612:03 pmPDX - MDW
1 stop10h 14mFrontier
Sun 2/27:15 amMDW - PDX
1 stop29h 46mFrontier
Deal found 1/15$230
This Mytrip deal was found by Cheapflights users on 1/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/275:30 pmPDX - ORD
2 stops25h 30mSpirit Airlines
Thu 1/3010:47 pmORD - PDX
1 stop12h 34mSpirit Airlines
Deal found 1/15$231
This Kissandfly.com deal was found by Cheapflights users on 1/15. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/62:40 pmPDX - MDW
2 stops19h 04mMultiple Airlines
Wed 2/127:05 amMDW - PDX
2 stops19h 51mMultiple Airlines
Deal found 1/15$235
This Southwest deal was found by Cheapflights users on 1/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/208:00 amPDX - MDW
Nonstop3h 55mSouthwest
Tue 2/258:30 amMDW - PDX
Nonstop4h 25mSouthwest
Deal found 1/14$238
This United Airlines deal was found by Cheapflights users on 1/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/127:00 amPDX - ORD
Nonstop4h 01mUnited Airlines
Tue 2/184:15 pmORD - PDX
Nonstop4h 33mUnited Airlines
Deal found 1/16$239
This Delta deal was found by Cheapflights users on 1/16. 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 9/1011:20 amPDX - ORD
1 stop7h 14mDelta
Sat 9/201:55 pmORD - PDX
1 stop6h 13mDelta
Deal found 1/16$247
This Delta deal was found by Cheapflights users on 1/16. 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 2/2412:59 amPDX - MDW
1 stop6h 36mDelta
Fri 2/281:26 pmMDW - PDX
1 stop6h 06mDelta
Deal found 1/16$258
This American Airlines deal was found by Cheapflights users on 1/16. 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 4/2311:55 pmPDX - ORD
Nonstop4h 05mAmerican Airlines
Tue 4/293:18 pmORD - PDX
1 stop8h 16mAmerican Airlines
Deal found 1/16$292
This Sun Country Air deal was found by Cheapflights users on 1/16. 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 6/1211:59 pmPDX - ORD
1 stop17h 12mSun Country Air
Sun 6/158:10 pmORD - PDX
1 stop28h 36mSun Country Air
Deal found 1/16$325

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 January 17, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 4/23

11:55 pm-6:00 am

Nonstop4h 05m

Chicago O'Hare Intl

Tue 4/29

10:05 am-12:32 pm

Nonstop4h 27m

$227

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 1/31

12:03 pm-12:32 am

1 stop10h 29m

Chicago O'Hare Intl

Mon 2/3

10:47 pm-4:35 pm

1 stop19h 48m

$228

PortlandChicago

PDX - ORD

PDXORD

Portland

Sun 1/26

12:03 pm-2:11 pm

1 stop24h 08m

Chicago O'Hare Intl

Thu 1/30

6:36 pm-9:45 am

1 stop17h 09m

$230

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sun 1/26

12:03 pm-12:17 am

1 stop10h 14m

Chicago Midway

Sun 2/2

7:15 am-11:01 am

1 stop29h 46m

$230

PortlandChicago

PDX - ORD

PDXORD

Portland

Mon 1/27

5:30 pm-9:00 pm

2 stops25h 30m

Chicago O'Hare Intl

Thu 1/30

10:47 pm-9:21 am

1 stop12h 34m

$231

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 2/8

6:05 am-2:03 pm

1 stop5h 58m

Chicago O'Hare Intl

Sat 2/15

4:05 pm-6:44 pm

Nonstop4h 39m

$232

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 2/6

2:40 pm-11:44 am

2 stops19h 04m

Chicago Midway

Wed 2/12

7:05 am-12:56 am

2 stops19h 51m

$235

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 2/20

8:00 am-1:55 pm

Nonstop3h 55m

Chicago Midway

Tue 2/25

8:30 am-10:55 am

Nonstop4h 25m

$238

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 2/12

7:00 am-1:01 pm

Nonstop4h 01m

Chicago O'Hare Intl

Tue 2/18

4:15 pm-6:48 pm

Nonstop4h 33m

$239

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 2/8

5:15 am-1:30 pm

1 stop6h 15m

Chicago O'Hare Intl

Wed 2/19

2:10 pm-8:50 pm

1 stop8h 40m

$247

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/15

Showing 1-10 of 29 results
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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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy2 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*1 star
CheapfaremartPrice Accuracy-Trust Score*1 star
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy2 starsTrust Score*2 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars

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

  • Most accurate provider: When it comes to deals on 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 January 10, 2025.

Booking 79 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 $320). 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 January 17, 2025.

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 40% 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 December 16, 2024.

Travelers seeking maximum savings on their Portland to Chicago flight should consider departing on Sunday afternoons when fares are most often at their lowest. Monday mornings 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 January 17, 2025.

The most flights from PDX to CHI are scheduled on a Thursday (16 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (7 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 January 17, 2025.
See what other customers who have flown with Spirit Airlines, Alaska Airlines and Southwest 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
4,659 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,681 reviews
Southwest
8.1
Very good
4,659 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,511 reviews
Southwest
8.1
Very good
4,659 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,965 reviews
Southwest
8.1
Very good
4,659 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Allegiant Air
7.4
Good
801 reviews
Southwest
8.1
Very good
4,659 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 11 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?

    American Airlines, at $227, was found to be the cheapest airline from Portland to Chicago.Alternate airlines to your destination round-trip include Spirit Airlines and Frontier. You may be able to fly from Portland to Chicago for 33% less than the average price by searching for these airlines.

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

    $109 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 Alaska Airlines, with prices starting from $110 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 (95%), SWISS (95%) or Lufthansa (93%) 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 $1,179, our data shows the cheapest flight currently is $128. When looking at the most popular route, (Portland - Chicago O'Hare Intl), you can expect to pay $142 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 $320). 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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Portland to Evansville flights
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Portland to Bloomington flights
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Portland to Dubuque flights
Portland to Champaign flights
Yakima to O'Hare Intl flights
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Boise to Bloomington flights
Portland to Rockford flights
Portland to Springfield flights
Medford to Bloomington flights
Eugene to Springfield flights
Eugene to Peoria flights
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Portland to Paducah flights
Boise to Springfield flights
Boise to Quincy flights
Boise to Champaign flights
Boise to Paducah flights
Redmond to Evansville flights
Redmond to Bloomington flights
North Bend to O'Hare Intl flights
Eugene to Dubuque flights
Portland to Marion flights

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 January 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$82Average$135FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$237FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$179Average$344FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$188Average$339FlexibilityNo cancel feeOn-time71%
DeltaCheapest$207Average$384FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$218Average$414FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$233Average$506FlexibilityNo cancel feeOn-time63%
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