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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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — CHI
Apr 26 — May 31
Sun 4/26
Sun 5/3
1 adult, Economy
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Find cheap flights from Portland to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

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Cheapflights Tip: The best prices from Portland to Chicago are usually found in January or August, booked 85 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 March 27, 2026.

This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/142:35 pm
PDX
-
ORD
1 stop7h 20m
Southwest
Tue 4/214:50 pm
ORD
-
PDX
1 stop8h 20m
Southwest
Deal found 3/22$222
This Booking.com deal was found by Cheapflights users on 3/22. 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.
Fri 4/179:54 am
PDX
-
ORD
1 stop17h 56m
Frontier
Wed 4/227:21 pm
ORD
-
PDX
1 stop18h 29m
Frontier
Deal found 3/22$223
This Southwest deal was found by Cheapflights users on 3/22. 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 5/55:40 am
PDX
-
MDW
Nonstop3h 55m
Southwest
Sat 5/96:05 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Deal found 3/22$223
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2811:55 pm
PDX
-
MDW
Nonstop3h 55m
Southwest
Sat 5/21:55 pm
MDW
-
PDX
1 stop6h 50m
Southwest
Deal found 3/22$226
This Southwest deal was found by Cheapflights users on 3/23. 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 4/157:55 pm
PDX
-
MDW
1 stop7h 05m
Southwest
Tue 4/214:00 pm
MDW
-
PDX
2 stops9h 10m
Southwest
Deal found 3/23$227
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2111:55 pm
PDX
-
MDW
Nonstop3h 55m
Southwest
Thu 4/239:50 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Deal found 3/23$231
This Kiwi.com deal was found by Cheapflights users on 3/26. 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.
Thu 6/45:31 pm
PDX
-
ORD
1 stop10h 36m
Frontier
Mon 6/89:42 pm
ORD
-
PDX
1 stop21h 15m
Frontier
Deal found 3/26$233
This Southwest deal was found by Cheapflights users on 3/22. 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 4/2311:55 pm
PDX
-
MDW
Nonstop3h 55m
Southwest
Wed 4/296:05 pm
MDW
-
PDX
1 stop7h 05m
Southwest
Deal found 3/22$234
This United Airlines deal was found by Cheapflights users on 3/26. 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.
Thu 4/2310:56 pm
PDX
-
ORD
Nonstop4h 04m
United Airlines
Thu 4/308:00 pm
ORD
-
PDX
Nonstop4h 35m
United Airlines
Deal found 3/26$235
This Southwest deal was found by Cheapflights users on 3/26. 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 4/2311:55 pm
PDX
-
MDW
Nonstop3h 55m
Southwest
Mon 4/279:50 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Deal found 3/26$235
This American Airlines deal was found by Cheapflights users on 3/24. 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.
Thu 6/41:45 pm
PDX
-
ORD
Nonstop4h 26m
American Airlines
Wed 6/107:29 am
ORD
-
PDX
Nonstop4h 30m
American Airlines
Deal found 3/24$236
This Kiwi.com deal was found by Cheapflights users on 3/26. 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.
Sat 4/1812:27 pm
PDX
-
ORD
1 stop19h 18m
Frontier
Mon 4/207:35 am
ORD
-
PDX
2 stops30h 17m
Frontier
Deal found 3/26$237

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 March 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$222
(Southwest)

One-way from

$109
(Super.com)

Popular in

November

Cheapest in

January

Average price

$389

Good round-trip deal

$347 or less

Good one-way deal

$173 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. 11% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 27, 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 - MDW

PDXMDW

Portland

Tue 4/14

7:55 pm-5:00 am

1 stop7h 05m

Chicago Midway

Mon 4/20

4:35 pm-12:55 am

2 stops10h 20m

$240

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 4/25

11:55 pm-5:50 am

Nonstop3h 55m

Chicago Midway

Sat 5/2

6:05 pm-8:25 pm

Nonstop4h 20m

$243

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 4/14

4:15 pm-12:30 am

1 stop6h 15m

Chicago O'Hare Intl

Mon 4/20

8:00 pm-10:34 pm

Nonstop4h 34m

$245

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 6/4

11:40 pm-5:45 am

Nonstop4h 05m

Chicago O'Hare Intl

Tue 6/9

5:00 am-9:47 am

1 stop6h 47m

$245

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 4/15

11:45 am-10:55 pm

2 stops9h 10m

Chicago O'Hare Intl

Wed 4/22

11:55 am-10:00 pm

2 stops12h 05m

$253

PortlandChicago

PDX - ORD

PDXORD

Portland

Mon 4/27

11:15 pm-10:19 am

1 stop9h 04m

Chicago O'Hare Intl

Sat 5/2

7:15 am-2:53 pm

1 stop9h 38m

$255

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 6/2

5:00 pm-11:13 pm

Nonstop4h 13m

Chicago O'Hare Intl

Sun 6/7

7:55 pm-10:30 pm

Nonstop4h 35m

$261

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 4/25

9:35 am-10:20 pm

1 stop10h 45m

Chicago O'Hare Intl

Sat 5/2

7:00 am-5:45 pm

1 stop12h 45m

$266

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 5/21

1:35 pm-9:20 pm

1 stop5h 45m

Chicago O'Hare Intl

Tue 5/26

5:19 pm-10:02 pm

1 stop6h 43m

$281

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 5/29

4:15 pm-12:44 am

1 stop6h 29m

Chicago O'Hare Intl

Mon 6/1

7:05 am-9:39 am

Nonstop4h 34m

$284

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

Showing 1-10 of 56 resultsSorted by cheapest first
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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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust Score*2 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice 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

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 March 13, 2026.

Booking 85 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 $125). Flying from Portland to Chicago in July is currently the most expensive (average of $238). 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 March 27, 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 18% 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 March 23, 2026.

Travelers seeking maximum savings on their Portland to Chicago flight should consider departing on Wednesday afternoons 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 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 March 27, 2026.

The most flights from PDX to CHI are scheduled on a Wednesday (21 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (6 on average).

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

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

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

Las Vegas (LAS) – chosen by Cheapflights users on 80% of 1-stop itineraries from Portland to Chicago on Cheapflights.

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

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

Las Vegas (LAS) is the most affordable 1-stop option, with an average round-trip price of $195.

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

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

Flights via Oakland (OAK) have the shortest average one-way travel time for 1-stop routes: 6h 30m.

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

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

Flights via Las Vegas (LAS) offer the fastest connection on this route, with an average layover time of 1h 41m.

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
Daniel Scheffler

Daniel Scheffler

Expert on Spirit Airlines

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

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 March 27, 2026.
Read reviews from past customers who have flown Southwest,Alaska Airlines, andHawaiian Airlines 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.
Southwest
8.0
Very good
4,334 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,334 reviews
Southwest
8.0
Very good
4,334 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Alaska Airlines
7.9
Good
12,126 reviews
Southwest
8.0
Very good
4,334 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Hawaiian Airlines
7.8
Good
2,839 reviews
Southwest
8.0
Very good
4,334 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,500 reviews
Southwest
8.0
Very good
4,334 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,514 reviews
Southwest
8.0
Very good
4,334 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 13 outbound flights to Chicago per day. 8 airlines have flights to Chicago from Portland on a regular basis.

  • How long is the flight from Portland to Chicago?

    For as low as $245, Southwest can have you in Chicago from Portland in 6h 15m. 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?

    Spirit 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 71% 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 Spirit Airlines and Southwest, with prices starting from $79 and $85, 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 Lufthansa (95%), Brussels Airlines (93%) or American Airlines (92%) 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 $903, our data shows the cheapest flight currently is $115. When looking at the most popular route, (Portland - Chicago O'Hare Intl), you can expect to pay $195 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 $125). Flying from Portland to Chicago in July is currently the most expensive (average of $238). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Top 8 airlines flying from Portland to Chicago

Discover the top 8 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 March 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$93Average$194FlexibilityNo cancel feeOn-time65%
FrontierCheapest$96Average$238FlexibilityNo cancel feeOn-time62%
DeltaCheapest$99Average$353FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$125Average$271FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$179Average$311FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$206Average$363FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$208Average$336FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$231Average$369FlexibilityNo cancel feeOn-time63%

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