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$90+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — CHI
Mar 31 — Apr 71
Mon 3/31
Mon 4/7
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 79 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 March 26, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$244
(United Airlines)

One-way from

$90
(Alaska Airlines)

Popular in

March

Cheapest in

January

Average price

$464

Good round-trip deal

$365 or less

Good one-way deal

$190 or less
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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Highest demand for flights based on searches. 7% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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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).
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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 March 26, 2025.

This United Airlines deal was found by Cheapflights users on 3/25. 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.
Fri 5/2310:59 pmPDX - ORD
Nonstop4h 01mUnited Airlines
Thu 5/296:30 amORD - PDX
1 stop8h 03mUnited Airlines
Deal found 3/25$244
This Booking.com deal was found by Cheapflights users on 3/25. 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 4/189:27 pmPDX - ORD
1 stop29h 34mMultiple Airlines
Sun 4/207:12 pmORD - PDX
1 stop16h 00mMultiple Airlines
Deal found 3/25$245
This Mytrip deal was found by Cheapflights users on 3/25. 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.
Thu 4/247:01 pmPDX - ORD
1 stop9h 32mSpirit Airlines
Thu 5/15:55 amORD - PDX
3 stops30h 02mSpirit Airlines
Deal found 3/25$246
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/3010:59 pmPDX - ORD
1 stop6h 56mDelta
Tue 5/66:25 pmORD - PDX
1 stop7h 31mDelta
Deal found 3/24$247
This Southwest deal was found by Cheapflights users on 3/25. 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 4/156:15 amPDX - MDW
Nonstop4h 00mSouthwest
Tue 4/224:30 pmMDW - PDX
Nonstop4h 20mSouthwest
Deal found 3/25$247
This Hawaiian 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/188:00 amPDX - ORD
1 stop8h 16mHawaiian Airlines
Sat 4/192:04 pmORD - PDX
Nonstop4h 32mHawaiian Airlines
Deal found 3/24$248
This American Airlines deal was found by Cheapflights users on 3/25. 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.
Fri 4/182:58 pmPDX - ORD
Nonstop4h 06mAmerican Airlines
Fri 4/258:20 pmORD - PDX
Nonstop4h 42mAmerican Airlines
Deal found 3/25$253
This Southwest deal was found by Cheapflights users on 3/25. 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 4/158:55 amPDX - ORD
1 stop5h 50mSouthwest
Tue 4/227:00 amORD - PDX
1 stop9h 10mSouthwest
Deal found 3/25$256
This Delta deal was found by Cheapflights users on 3/25. 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 4/1412:59 amPDX - MDW
1 stop6h 41mDelta
Tue 4/223:02 pmMDW - PDX
1 stop9h 07mDelta
Deal found 3/25$257
This Alaska Airlines deal was found by Cheapflights users on 3/25. 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 6/145:35 pmPDX - ORD
Nonstop4h 04mAlaska Airlines
Sun 6/227:00 amORD - PDX
Nonstop4h 25mAlaska Airlines
Deal found 3/25$258
This Frontier deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/19:59 amPDX - MDW
1 stop12h 22mFrontier
Fri 4/48:50 pmMDW - PDX
1 stop13h 57mFrontier
Deal found 3/25$278
This CheapOair deal was found by Cheapflights users on 3/25. 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.
Wed 4/29:54 amPDX - ORD
1 stop12h 48mFrontier
Sun 4/67:39 pmORD - PDX
1 stop15h 08mFrontier
Deal found 3/25$281

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 26, 2025.
Use the filters below to find and compare flights from Portland to Chicago that are best for you.

Fly from

Portland

Fly to

Chicago

Route

Depart

Return

Price

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 5/23

11:59 pm-6:04 am

Nonstop4h 05m

Chicago O'Hare Intl

Wed 5/28

2:33 pm-8:47 pm

1 stop8h 14m

$244

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 4/18

9:27 pm-5:01 am

1 stop29h 34m

Chicago O'Hare Intl

Sun 4/20

7:12 pm-9:12 am

1 stop16h 00m

$245

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 4/24

7:01 pm-6:33 am

1 stop9h 32m

Chicago O'Hare Intl

Thu 5/1

5:55 am-9:57 am

3 stops30h 02m

$246

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 4/30

10:59 pm-7:55 am

1 stop6h 56m

Chicago O'Hare Intl

Tue 5/6

6:25 pm-11:56 pm

1 stop7h 31m

$247

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 4/15

6:15 am-12:15 pm

Nonstop4h 00m

Chicago Midway

Tue 4/22

4:30 pm-6:50 pm

Nonstop4h 20m

$247

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 4/18

8:00 am-6:16 pm

1 stop8h 16m

Chicago O'Hare Intl

Sat 4/19

2:04 pm-4:36 pm

Nonstop4h 32m

$248

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 4/18

2:58 pm-9:04 pm

Nonstop4h 06m

Chicago O'Hare Intl

Fri 4/25

8:20 pm-11:02 pm

Nonstop4h 42m

$253

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 4/15

5:20 pm-5:40 am

1 stop10h 20m

Chicago O'Hare Intl

Tue 4/22

6:58 pm-9:48 am

1 stop16h 50m

$256

PortlandChicago

PDX - MDW

PDXMDW

Portland

Mon 4/14

12:59 am-9:40 am

1 stop6h 41m

Chicago Midway

Tue 4/22

3:02 pm-10:09 pm

1 stop9h 07m

$257

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 4/1

9:59 am-12:21 am

1 stop12h 22m

Chicago Midway

Sat 4/12

8:59 pm-8:47 am

1 stop13h 48m

$278

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

Showing 1-10 of 31 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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
Kiwi.comPrice Accuracy3 starsTrust Score*2 stars
CheapfaremartPrice Accuracy-Trust Score*3 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.

The best insider tips for Portland to Chicago flights

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

Basic Economy allows a personal item only; no carry-on bags unless exceptions apply.


Economy Plus offers extra legroom and is free for MileagePlus Premier members.

Read more about United Airlinesby Harriet Baskas
Alaska Airlines

Alaska's Premium Class offers extra legroom and free cocktails.


Alaska's Wi-Fi is available for a flat fee, ideal for business travelers.

Read more about Alaska Airlinesby Robert Schrader
Spirit Airlines

Spirit's Big Front Seats provide 11 inches more legroom, ideal for comfort.


Use Spirit's Bag-O-Tron tool to compare baggage fees and save money.

Read more about Spirit Airlinesby Daniel Scheffler
Airports
PDX

For expedited security, PDX offers Express Lanes for first and business class tickets, elite status, and uniformed military personnel.

Read more about PDXby Brandon Schultz
ORD

For a quick city transfer, take the “L” train from ORD to downtown Chicago, avoiding potential traffic delays with taxis or rideshares.

Read more about ORDby Ramsey Qubein
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet Baskas

Harriet Baskas

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

Robert Schrader

Robert Schrader

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

Read more
Daniel Scheffler

Daniel Scheffler

Expert on Spirit Airlines

Daniel Scheffler

Daniel Scheffler

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

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD

Ramsey Qubein

Ramsey Qubein

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

Read more
Brandon Schultz

Brandon Schultz

Expert on PDX

Brandon Schultz

Brandon Schultz

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

Read more

Best time to book a flight from 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 21, 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 $323). 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 26, 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 35% 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, 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.

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 March 26, 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
4,273 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Crew

8.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.1
Very good
4,273 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Crew

8.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Alaska Airlines
8.0
Very good
9,789 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Crew

8.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,891 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Crew

8.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Hawaiian Airlines
7.9
Good
2,331 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Crew

8.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,608 reviews
Southwest
8.1
Very good
4,273 reviews

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Crew

8.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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

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

    United Airlines, at $244, 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 28% less than the average price by searching for these airlines.

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

    $90 is the cheapest one-way deal found within the past few days, from Alaska Airlines. You may also be able to find cheap deals on Spirit Airlines and Hawaiian Airlines, with prices starting from $91 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 Lufthansa (96%), United Airlines (94%) or Air Canada (94%) 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 $1,439, our data shows the cheapest flight currently is $124. When looking at the most popular route, (Portland - Chicago O'Hare Intl), you can expect to pay $176 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 $323). 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
Boise to O'Hare Intl flights
Portland to St. Louis flights
Eugene to O'Hare Intl flights
Redmond to O'Hare Intl flights
Boise to Midway flights
Eugene to Midway flights
Redmond to Midway flights
Portland to Peoria flights
Eugene to St. Louis flights
Boise to St. Louis flights
Medford to O'Hare Intl flights
Portland to Rockford flights
Portland to Decatur flights
Medford to St. Louis flights
Medford to Midway flights
Portland to Moline flights
Portland to Bloomington flights
Boise to Moline flights
Redmond to St. Louis flights
Boise to Peoria flights
Portland to Champaign flights
Portland to Springfield flights
Yakima to O'Hare Intl flights
Portland to Evansville flights
Medford to Bloomington flights
Boise to Springfield flights
Eugene to Moline flights
Boise to Bloomington flights
Portland to Dubuque flights
Boise to Champaign flights
Boise to Paducah flights
Redmond to Evansville flights
Redmond to Bloomington flights
Boise to Quincy flights
Eugene to Dubuque flights
Eugene to Peoria flights
Portland to Paducah flights
Eugene to Springfield flights
Portland to Marion flights
North Bend to O'Hare Intl flights

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 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$82Average$135FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$241FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$185Average$340FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$189Average$334FlexibilityNo cancel feeOn-time71%
Hawaiian AirlinesCheapest$202Average$383FlexibilityNo cancel feeOn-time85%
DeltaCheapest$207Average$377FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$215Average$404FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$249Average$414FlexibilityNo cancel feeOn-time63%
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