Basic Economy allows a personal item only; no carry-on bags unless exceptions apply.
Prepay checked bags 24 hours before to save on fees.
$114+ Cheap flights from Portland (PDX) to O'Hare Intl (ORD)
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 7/16. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Apr 27 — May 41
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Portland to O'Hare Intl 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”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Portland to Chicago O'Hare Intl are usually found in August or January, booked 73 days in advance, depart on a Wednesday or Thursday and return on a Wednesday
Cheap flight deals from Portland to O'Hare Intl
Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to O'Hare Intl (ORD). 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 April 22, 2025.
Most accurate provider | Mytrip 3 stars |
|---|---|
Most trusted provider | Mytrip 3 stars |
Round-trip from | $241 (FlightHub) |
One-way from | $114 (American Airlines) |
Popular in | December |
Cheapest in | August |
Average price | $348 |
Good round-trip deal | $358 or less |
Good one-way deal | $170 or less |
Find flight deals from Portland to O'Hare Intl
Cheapest flights from Portland to O'Hare IntlExplore the most affordable flight options available from Portland to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 22, 2025.
Explore the most affordable flight options available from Portland to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 22, 2025.
This Priceline deal was found by Cheapflights users on 4/22. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/115:40 pmPDX - ORD
2 stops13h 15mMultiple Airlines
Fri 5/165:21 pmORD - PDX
1 stop9h 17mMultiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$236
This Hawaiian Airlines deal was found by Cheapflights users on 4/22. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/55:51 pmPDX - ORD
Nonstop4h 05mHawaiian Airlines
Tue 6/107:00 amORD - PDX
Nonstop4h 23mHawaiian Airlines
Deal found 4/22![Hawaiian Airlines logo]()
$238
This Mytrip deal was found by Cheapflights users on 4/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/225:40 pmPDX - ORD
1 stop15h 15mSpirit Airlines
Tue 5/279:14 pmORD - PDX
2 stops17h 28mSpirit Airlines
Deal found 4/22![Spirit Airlines logo]()
$239
This United Airlines deal was found by Cheapflights users on 4/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/202:14 pmPDX - ORD
Nonstop4h 03mUnited Airlines
Tue 5/275:02 amORD - PDX
1 stop6h 37mUnited Airlines
Deal found 4/22![United Airlines logo]()
$242
This Alaska Airlines deal was found by Cheapflights users on 4/22. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/301:25 pmPDX - ORD
1 stop6h 58mAlaska Airlines
Mon 6/27:00 amORD - PDX
Nonstop4h 23mAlaska Airlines
Deal found 4/22![Alaska Airlines logo]()
$244
This CheapOair deal was found by Cheapflights users on 4/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/259:38 pmPDX - ORD
1 stop12h 51mFrontier
Sun 4/278:07 pmORD - PDX
1 stop15h 05mFrontier
Deal found 4/22![Frontier logo]()
$260
This American Airlines deal was found by Cheapflights users on 4/21. 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.
Sat 5/246:00 amPDX - ORD
1 stop7h 55mAmerican Airlines
Fri 5/308:25 pmORD - PDX
Nonstop4h 34mAmerican Airlines
Deal found 4/21![American Airlines logo]()
$270
This Sun Country Air deal was found by Cheapflights users on 4/22. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/1511:59 pmPDX - ORD
1 stop15h 22mSun Country Air
Thu 6/196:17 pmORD - PDX
1 stop6h 29mSun Country Air
Deal found 4/22![Sun Country Air logo]()
$285
This Delta deal was found by Cheapflights users on 4/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/123:15 pmPDX - ORD
1 stop6h 29mDelta
Sun 7/137:05 amORD - PDX
1 stop9h 32mDelta
Deal found 4/22![Delta logo]()
$289
This Southwest deal was found by Cheapflights users on 4/20. 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 6/35:20 amPDX - ORD
1 stop6h 40mSouthwest
Sat 6/147:00 amORD - PDX
2 stops9h 45mSouthwest
Deal found 4/20![Southwest logo]()
$342
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to O'Hare Intl 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 April 22, 2025.
Use the filters below to find and compare flights from Portland to Chicago O'Hare Intl Airport that are best for you.
Fly from
Portland
Fly to
O'Hare Intl
Route
Depart
Return
Price
PortlandChicago
PDX - ORD
PDXORD
Portland
Sun 5/11
5:40 pm-8:55 am
2 stops13h 15m
Chicago O'Hare Intl
Fri 5/16
5:21 pm-12:38 am
1 stop9h 17m
$236
PortlandChicago
PDX - ORD
PDXORD
Portland
Thu 6/5
5:51 pm-11:56 pm
Nonstop4h 05m
Chicago O'Hare Intl
Tue 6/10
7:00 am-9:23 am
Nonstop4h 23m
$238
PortlandChicago
PDX - ORD
PDXORD
Portland
Thu 5/22
5:40 pm-10:55 am
1 stop15h 15m
Chicago O'Hare Intl
Tue 5/27
9:14 pm-12:42 pm
2 stops17h 28m
$239
PortlandChicago
PDX - ORD
PDXORD
Portland
Tue 5/20
2:14 pm-8:17 pm
Nonstop4h 03m
Chicago O'Hare Intl
Tue 5/27
5:02 am-9:39 am
1 stop6h 37m
$242
PortlandChicago
PDX - ORD
PDXORD
Portland
Fri 5/30
1:25 pm-10:23 pm
1 stop6h 58m
Chicago O'Hare Intl
Mon 6/2
7:00 am-9:23 am
Nonstop4h 23m
$244
PortlandChicago
PDX - ORD
PDXORD
Portland
Fri 4/25
9:38 pm-12:29 pm
1 stop12h 51m
Chicago O'Hare Intl
Sun 4/27
8:07 pm-9:12 am
1 stop15h 05m
$260
PortlandChicago
PDX - ORD
PDXORD
Portland
Sat 5/24
6:00 am-3:55 pm
1 stop7h 55m
Chicago O'Hare Intl
Fri 5/30
8:25 pm-10:59 pm
Nonstop4h 34m
$270
PortlandChicago
PDX - ORD
PDXORD
Portland
Sun 6/15
11:59 pm-5:21 pm
1 stop15h 22m
Chicago O'Hare Intl
Thu 6/19
6:17 pm-10:46 pm
1 stop6h 29m
$285
PortlandChicago
PDX - ORD
PDXORD
Portland
Fri 5/23
12:40 am-8:24 am
1 stop5h 44m
Chicago O'Hare Intl
Wed 5/28
6:20 pm-12:10 am
1 stop7h 50m
$286
PortlandChicago
PDX - ORD
PDXORD
Portland
Tue 6/3
5:20 am-2:00 pm
1 stop6h 40m
Chicago O'Hare Intl
Sat 6/14
7:00 am-2:45 pm
2 stops9h 45m
$342
Showing 1-10 of 20 results
Compare providers for flights from Portland to O'Hare Intl
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 O'Hare Intl in April.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Portland-Chicago O'Hare Intl Airport flights, users find the pricing of Mytrip to be most consistent on Cheapflights vs. Mytrip Users can find the same prices on Portland-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. Mytrip >95% of the time. Price accuracy is based on data collected from Portland-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Portland-Chicago O'Hare Intl Airport flights, Cheapflights users trust Mytrip the most. Mytrip 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 O'Hare Intl Airport 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 O'Hare Intl Airport 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 O'Hare Intl Airport trip
Airlines
![United Airlines]()
United Airlines
![Alaska Airlines]()
Alaska Airlines
Saver Fare allows a carry-on; seat selection is restricted.
Alaska offers Wi-Fi for a flat fee, ideal for business travelers.
![Spirit Airlines]()
Spirit Airlines
Spirit's Big Front Seats offer 11 inches more legroom.
Add bags during purchase for best prices; use Spirit's Bag-O-Tron tool.
Airports
Our travel experts
Best time to book a flight from Portland to O'Hare Intl
Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl 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 O'Hare Intl Airport
How far ahead should I book a flight from Portland to Chicago O'Hare Intl Airport?
Use this chart to determine the optimal time to book a round-trip flight from Portland to O'Hare Intl. Price data was last updated on April 18, 2025.
Booking 73 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland to Chicago O'Hare Intl Airport. 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 O'Hare Intl Airport?
Currently, August is the cheapest month in which you can book a flight from Portland to Chicago O'Hare Intl Airport (average of $245). Flying from Portland to Chicago O'Hare Intl Airport 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 ORD?
Find hourly flight availability from Portland to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 22, 2025.
When flying from Portland to Chicago O'Hare Intl Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 38% versus a flight in the morning.
What is the cheapest day to fly from Portland to Chicago O'Hare Intl Airport?
Use this chart to determine the cheapest time to fly round-trip from Portland to O'Hare Intl. Price data was last updated on March 30, 2025.
Travelers seeking maximum savings on their Portland to Chicago O'Hare Intl Airport 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.
Weekly flight availability from Portland to Chicago O'Hare Intl Airport
Explore weekly flight availability from Portland to O'Hare Intl. 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 April 22, 2025.
The most flights from PDX to ORD are scheduled on a Monday (20 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 on average).
Rainfall in O'Hare Intl by month
Plan your trip to O'Hare Intl by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago O'Hare Intl Airport 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 O'Hare Intl Airport when rainfall is around 1.7 in.
Temperature in O'Hare Intl by month
Plan your trip to O'Hare Intl by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago O'Hare Intl Airport, 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 O'Hare Intl
Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated April 22, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest and Delta from Portland to Chicago to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
7.1
Boarding
8.2
Entertainment
7.1
Overall
8.0
Comfort
7.9
Crew
8.5
Reviews
1 / 20
4.0
OkayAnonymous,Apr 2025
LAS - STS
Food
7.1
Boarding
8.2
Entertainment
7.1
Overall
8.0
Comfort
7.9
Crew
8.5
Reviews
1 / 20
4.0
OkayAnonymous,Apr 2025
LAS - STS
Food
7.1
Boarding
8.2
Entertainment
7.1
Overall
8.0
Comfort
7.9
Crew
8.5
Reviews
1 / 20
4.0
OkayAnonymous,Apr 2025
LAS - STS
Food
7.1
Boarding
8.2
Entertainment
7.1
Overall
8.0
Comfort
7.9
Crew
8.5
Reviews
1 / 20
4.0
OkayAnonymous,Apr 2025
LAS - STS
Food
7.1
Boarding
8.2
Entertainment
7.1
Overall
8.0
Comfort
7.9
Crew
8.5
Reviews
1 / 20
4.0
OkayAnonymous,Apr 2025
LAS - STS
Food
7.1
Boarding
8.2
Entertainment
7.1
Overall
8.0
Comfort
7.9
Crew
8.5
Reviews
1 / 20
4.0
OkayAnonymous,Apr 2025
LAS - STS
Related info for your journey
Find useful and relevant information for your journey from Portland to O'Hare Intl. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Portland?
Book flights to Portland if you plan to visit one of these locationsSchaumburg
Hoffman Estates
Rosemont
Beloit
Racine
Skokie
Naperville
Tinley Park
Kenosha
Rockford
Arlington Heights
Elgin
Joliet
Orland Park
Merrillville
Northbrook
Des Plaines
Lake Geneva
Waukegan
Glenview
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes for Portland to O'Hare Intl
See prices for flight routes from nearby airports that may be better suited for you.
Top 7 airlines flying from Portland to O'Hare Intl
Discover the top 7 airlines that operate flights from Portland to O'Hare Intl. 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 April 22, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$82 | Average$132 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$108 | Average$178 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$123 | Average$287 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$185 | Average$341 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$193 | Average$337 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$202 | Average$362 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$214 | Average$397 | FlexibilityNo cancel fee | On-time69% |