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$100+ 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 11/4. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — CHI
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Chicago are usually found in January or August, booked 84 days in advance, depart on a Friday 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 July 3, 2025.

Round-trip from

$216
(CheapOair)

One-way from

$101
(FlightHub)

Popular in

March

Cheapest in

January

Average price

$317

Good round-trip deal

$320 or less

Good one-way deal

$182 or less
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. 10% potential increase in price ($38 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This CheapOair deal was found by Cheapflights users on 7/1. 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.
Tue 7/153:10 pmPDX - ORD
1 stop12h 53mSpirit Airlines
Sat 7/197:49 pmORD - PDX
1 stop15h 29mSpirit Airlines
Deal found 7/1$216
This Travelocity deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/207:15 amPDX - ORD
1 stop12h 13mMultiple Airlines
Wed 9/242:07 pmORD - PDX
Nonstop4h 30mMultiple Airlines
Deal found 7/2$217
This Priceline deal was found by Cheapflights users on 7/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1811:00 amPDX - ORD
1 stop8h 06mFrontier
Mon 7/215:40 amORD - PDX
1 stop6h 31mFrontier
Deal found 7/3$218
This Southwest deal was found by Cheapflights users on 7/2. 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.
Sat 8/236:50 amPDX - MDW
2 stops7h 45mSouthwest
Sat 8/308:20 amMDW - PDX
Nonstop4h 15mSouthwest
Deal found 7/2$218
This Delta deal was found by Cheapflights users on 7/2. 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.
Fri 8/2212:46 amPDX - MDW
1 stop6h 05mDelta
Sat 8/307:17 pmMDW - PDX
1 stop6h 14mDelta
Deal found 7/2$223
This United Airlines deal was found by Cheapflights users on 7/1. 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 8/287:35 pmPDX - ORD
1 stop7h 48mUnited Airlines
Sun 8/311:05 pmORD - PDX
Nonstop4h 20mUnited Airlines
Deal found 7/1$224
This Southwest deal was found by Cheapflights users on 7/2. 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.
Sat 8/239:55 amPDX - ORD
2 stops10h 05mSouthwest
Sat 8/307:00 amORD - PDX
1 stop8h 10mSouthwest
Deal found 7/2$228
This Mytrip deal was found by Cheapflights users on 7/2. 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.
Fri 8/15:50 pmPDX - MDW
1 stop25h 04mFrontier
Mon 8/1112:35 pmMDW - PDX
1 stop24h 55mFrontier
Deal found 7/2$229
This Alaska Airlines deal was found by Cheapflights users on 7/2. 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.
Fri 10/3110:00 pmPDX - ORD
1 stop6h 22mAlaska Airlines
Mon 11/36:00 amORD - PDX
1 stop8h 29mAlaska Airlines
Deal found 7/2$234
This Hawaiian Airlines deal was found by Cheapflights users on 6/30. 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.
Wed 9/172:32 pmPDX - ORD
1 stop7h 31mHawaiian Airlines
Wed 9/242:07 pmORD - PDX
Nonstop4h 30mHawaiian Airlines
Deal found 6/30$235
This American Airlines deal was found by Cheapflights users on 7/1. 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 7/3011:54 pmPDX - ORD
Nonstop3h 56mAmerican Airlines
Mon 8/47:25 amORD - PDX
Nonstop4h 26mAmerican Airlines
Deal found 7/1$240
This Delta deal was found by Cheapflights users on 7/1. 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.
Tue 12/21:37 pmPDX - ORD
1 stop8h 10mDelta
Tue 12/96:59 pmORD - PDX
1 stop6h 49mDelta
Deal found 7/1$247

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 July 3, 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

Tue 7/15

3:10 pm-6:03 am

1 stop12h 53m

Chicago O'Hare Intl

Sat 7/19

7:49 pm-9:18 am

1 stop15h 29m

$216

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 9/20

7:15 am-9:28 pm

1 stop12h 13m

Chicago O'Hare Intl

Sat 9/27

2:07 pm-4:37 pm

Nonstop4h 30m

$217

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 7/18

11:00 am-9:06 pm

1 stop8h 06m

Chicago O'Hare Intl

Mon 7/21

5:40 am-10:11 am

1 stop6h 31m

$218

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 8/23

6:50 am-4:35 pm

2 stops7h 45m

Chicago Midway

Sat 8/30

8:20 am-10:35 am

Nonstop4h 15m

$218

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 8/22

12:46 am-8:51 am

1 stop6h 05m

Chicago Midway

Sat 8/30

7:17 pm-11:31 pm

1 stop6h 14m

$223

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 8/28

7:35 pm-5:23 am

1 stop7h 48m

Chicago O'Hare Intl

Sun 8/31

1:05 pm-3:25 pm

Nonstop4h 20m

$224

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 8/23

9:55 am-10:00 pm

2 stops10h 05m

Chicago O'Hare Intl

Sat 8/30

7:00 am-1:10 pm

1 stop8h 10m

$228

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 8/1

5:50 pm-8:54 pm

1 stop25h 04m

Chicago Midway

Mon 8/11

12:35 pm-11:30 am

1 stop24h 55m

$229

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 10/31

10:15 am-8:58 pm

1 stop8h 43m

Chicago O'Hare Intl

Mon 11/3

7:30 am-2:39 pm

1 stop9h 09m

$234

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 9/17

2:32 pm-12:03 am

1 stop7h 31m

Chicago O'Hare Intl

Wed 9/24

2:07 pm-4:37 pm

Nonstop4h 30m

$235

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Showing 1-10 of 26 results
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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

Expect security wait times up to 15 minutes off-peak, and over 30 minutes during rush hours. Use Express Lanes if eligible for faster processing.

Read more about PDXby Brandon Schultz
ORD

Take the “L” train from ORD to downtown Chicago for a reliable and cost-effective option. Avoid traffic delays common with taxis or rideshares.

Read more about ORDby Ramsey Qubein
MDW

Use the Orange Line train from MDW to reach downtown Chicago in under 30 minutes, offering a cheap and convenient travel option.

Read more about MDWby 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 and MDW

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 June 27, 2025.

Booking 84 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 July 3, 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 41% 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 June 29, 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 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 July 3, 2025.

The most flights from PDX to CHI are scheduled on a Thursday (32 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (7 on average).

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 July 3, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest, and Delta from Portland to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.1

Food

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.1

Food

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,266 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.1

Food

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,982 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.1

Food

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.8
Good
2,545 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.1

Food

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,861 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Crew

8.5

Entertainment

7.1

Boarding

8.1

Food

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 18 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?

    Spirit Airlines, at $216, was found to be the cheapest airline from Portland to Chicago.Alternate airlines to your destination round-trip include Frontier and Southwest. You may be able to fly from Portland to Chicago for 36% less than the average price by searching for these airlines.

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

    $101 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 $102 and $112, 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 United Airlines (83%), SWISS (83%) or Brussels Airlines (82%) 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 $1,168, 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 $156 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
Lansing
Benton Harbor
Porter
Hammond
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.
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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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$87Average$146FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$233FlexibilityNo cancel feeOn-time62%
DeltaCheapest$123Average$288FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$187Average$334FlexibilityNo cancel feeOn-time75%
Hawaiian AirlinesCheapest$202Average$293FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$217Average$398FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$227Average$333FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$249Average$434FlexibilityNo cancel feeOn-time63%

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