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$93+ 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 7/9. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — CHI
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
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 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 junio 12, 2025.

Round-trip from

$210
(Cheapflightsfares)

One-way from

$93
(FlightHub)

Popular in

March

Cheapest in

January

Average price

$341

Good round-trip deal

$342 or less

Good one-way deal

$171 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 ($39 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 June 2025
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Price to beat on a round-trip flight from Portland to Chicago (CHI).
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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 junio 12, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 6/256:39 pmPDX - ORD
1 stop14h 11mSpirit Airlines
dom. 6/2910:15 pmORD - PDX
1 stop15h 02mSpirit Airlines
Deal found 6/12$210
This Southwest deal was found by Cheapflights users on 6/12. 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.
mié. 9/1011:45 amPDX - MDW
1 stop8h 05mSouthwest
dom. 9/1410:25 pmMDW - PDX
Nonstop4h 15mSouthwest
Deal found 6/12$211
This Southwest deal was found by Cheapflights users on 6/10. 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.
mar. 9/26:10 amPDX - ORD
1 stop6h 00mSouthwest
jue. 9/181:30 pmORD - PDX
1 stop8h 40mSouthwest
Deal found 6/10$213
This Hawaiian Airlines deal was found by Cheapflights users on 6/10. 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.
jue. 8/145:35 pmPDX - ORD
Nonstop4h 04mHawaiian Airlines
dom. 8/177:00 amORD - PDX
Nonstop4h 25mHawaiian Airlines
Deal found 6/10$214
This Alaska Airlines deal was found by Cheapflights users on 6/10. 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.
jue. 10/302:31 pmPDX - ORD
1 stop7h 28mAlaska Airlines
dom. 11/27:00 amORD - PDX
Nonstop4h 38mAlaska Airlines
Deal found 6/10$224
This United Airlines deal was found by Cheapflights users on 6/11. 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.
sáb. 7/1211:59 pmPDX - ORD
Nonstop4h 01mUnited Airlines
mar. 7/157:55 pmORD - PDX
Nonstop4h 34mUnited Airlines
Deal found 6/11$227
This Booking.com deal was found by Cheapflights users on 6/10. 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.
vie. 7/2511:59 pmPDX - ORD
1 stop15h 28mMultiple Airlines
sáb. 8/27:49 pmORD - PDX
1 stop15h 29mMultiple Airlines
Deal found 6/10$236
This Delta deal was found by Cheapflights users on 6/12. 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.
lun. 7/1412:40 amPDX - MDW
1 stop6h 05mDelta
mar. 7/229:24 amMDW - PDX
1 stop8h 31mDelta
Deal found 6/12$247
This Delta deal was found by Cheapflights users on 6/11. 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.
vie. 7/41:45 pmPDX - ORD
1 stop5h 52mDelta
sáb. 7/125:20 pmORD - PDX
1 stop6h 41mDelta
Deal found 6/11$254
This Mytrip deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/63:10 pmPDX - RFD
1 stop18h 44mMultiple Airlines
dom. 8/1012:44 pmRFD - PDX
1 stop22h 34mMultiple Airlines
Deal found 6/9$265
This FlightHub deal was found by Cheapflights users on 6/12. 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.
jue. 9/116:05 amPDX - MDW
1 stop14h 33mFrontier
lun. 9/154:29 pmMDW - PDX
1 stop9h 47mFrontier
Deal found 6/12$280
This American Airlines deal was found by Cheapflights users on 6/11. 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.
mié. 7/3012:40 pmPDX - ORD
Nonstop4h 03mAmerican Airlines
dom. 8/37:25 amORD - PDX
Nonstop4h 26mAmerican Airlines
Deal found 6/11$283

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 junio 12, 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

mié. 6/25

6:39 pm-10:50 am

1 stop14h 11m

Chicago O'Hare Intl

dom. 6/29

10:15 pm-11:17 am

1 stop15h 02m

$210

PortlandChicago

PDX - MDW

PDXMDW

Portland

mié. 9/10

11:45 am-9:50 pm

1 stop8h 05m

Chicago Midway

dom. 9/14

10:25 pm-12:40 am

Nonstop4h 15m

$211

PortlandChicago

PDX - ORD

PDXORD

Portland

mar. 9/2

6:10 am-2:10 pm

1 stop6h 00m

Chicago O'Hare Intl

jue. 9/18

1:30 pm-8:10 pm

1 stop8h 40m

$213

PortlandChicago

PDX - ORD

PDXORD

Portland

jue. 8/14

5:35 pm-11:39 pm

Nonstop4h 04m

Chicago O'Hare Intl

dom. 8/17

7:00 am-9:25 am

Nonstop4h 25m

$214

PortlandChicago

PDX - ORD

PDXORD

Portland

jue. 10/30

2:31 pm-11:59 pm

1 stop7h 28m

Chicago O'Hare Intl

dom. 11/2

7:00 am-9:38 am

Nonstop4h 38m

$224

PortlandChicago

PDX - ORD

PDXORD

Portland

mar. 7/1

11:59 pm-6:00 am

Nonstop4h 01m

Chicago O'Hare Intl

jue. 7/3

9:10 am-11:43 am

Nonstop4h 33m

$234

PortlandChicago

PDX - ORD

PDXORD

Portland

vie. 7/25

11:59 pm-5:27 pm

1 stop15h 28m

Chicago O'Hare Intl

sáb. 8/2

7:49 pm-9:18 am

1 stop15h 29m

$236

PortlandChicago

PDX - MDW

PDXMDW

Portland

mar. 7/15

11:11 pm-8:44 am

1 stop7h 33m

Chicago Midway

mar. 7/22

9:24 am-3:55 pm

1 stop8h 31m

$247

PortlandChicago

PDX - ORD

PDXORD

Portland

vie. 7/4

1:45 pm-9:37 pm

1 stop5h 52m

Chicago O'Hare Intl

sáb. 7/12

5:20 pm-10:01 pm

1 stop6h 41m

$254

PortlandChicago

PDX - RFD

PDXRFD

Portland

mié. 8/6

3:10 pm-11:54 am

1 stop18h 44m

Chicago Greater Rockford

dom. 8/10

12:44 pm-9:18 am

1 stop22h 34m

$265

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

Showing 1-10 of 31 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 9, 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 junio 12, 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 42% 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 8, 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 junio 12, 2025.

The most flights from PDX to CHI are scheduled on a Thursday (33 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (20 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 junio 12, 2025.
See what other customers who have flown with Alaska Airlines, Southwest 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Crew

8.5

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

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Crew

8.5

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
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Crew

8.5

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
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,494 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Crew

8.5

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
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Crew

8.5

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 26 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 $210, was found to be the cheapest airline from Portland to Chicago.Alternate airlines to your destination round-trip include Southwest and Hawaiian Airlines. You may be able to fly from Portland to Chicago for 38% less than the average price by searching for these airlines.

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

    $93 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 United Airlines and Southwest, with prices starting from $95 and $99, 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 SWISS (87%), Finnair (87%) or Brussels Airlines (84%) 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 $1,280, our data shows the cheapest flight currently is $113. 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 $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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$86Average$135FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$219FlexibilityNo cancel feeOn-time62%
DeltaCheapest$123Average$342FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$186Average$337FlexibilityNo cancel feeOn-time75%
Hawaiian AirlinesCheapest$202Average$294FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$217Average$399FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$226Average$342FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$253Average$437FlexibilityNo cancel feeOn-time63%

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