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.
$110+ 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — CHI
maj 11 — maj 181
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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”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 are usually found in January or August, booked 77 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 maj 6, 2025.
Most accurate provider | CheapOair 3 stars |
|---|---|
Most trusted provider | CheapOair 3 stars |
Round-trip from | $223 (Kiwi.com) |
One-way from | $110 (American Airlines) |
Popular in | March |
Cheapest in | January |
Average price | $328 |
Good round-trip deal | $357 or less |
Good one-way deal | $169 or less |
Find flight deals from Portland to Chicago
Cheapest flights from Portland to ChicagoExplore 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 maj 6, 2025.
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 maj 6, 2025.
This Cheapflightsfares deal was found by Cheapflights users on 5/6. 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.
tor. 7/312:35 pmPDX - ORD
1 stop7h 08mSpirit Airlines
man. 8/48:51 pmORD - PDX
1 stop15h 24mSpirit Airlines
Deal found 5/6![Spirit Airlines logo]()
$222
This Hawaiian Airlines deal was found by Cheapflights users on 5/6. 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.
ons. 7/25:35 pmPDX - ORD
Nonstop4h 04mHawaiian Airlines
lør. 7/127:00 amORD - PDX
Nonstop4h 25mHawaiian Airlines
Deal found 5/6![Hawaiian Airlines logo]()
$223
This Delta deal was found by Cheapflights users on 5/5. 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.
man. 6/2312:52 amPDX - MDW
1 stop5h 52mDelta
tir. 7/17:21 pmMDW - PDX
1 stop6h 11mDelta
Deal found 5/5![Delta logo]()
$223
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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.
fre. 5/235:51 pmPDX - ORD
Nonstop4h 05mAlaska Airlines
tir. 5/277:00 amORD - PDX
Nonstop4h 23mAlaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$224
This Southwest deal was found by Cheapflights users on 5/5. 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.
man. 5/125:30 amPDX - MDW
Nonstop4h 00mSouthwest
man. 5/124:15 pmMDW - PDX
Nonstop4h 20mSouthwest
Deal found 5/5![Southwest logo]()
$224
This Delta deal was found by Cheapflights users on 5/6. 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.
ons. 5/2812:40 amPDX - ORD
1 stop5h 44mDelta
tir. 6/32:25 pmORD - PDX
1 stop8h 27mDelta
Deal found 5/6![Delta logo]()
$225
This United Airlines deal was found by Cheapflights users on 5/5. 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.
tor. 5/222:12 pmPDX - ORD
Nonstop4h 13mUnited Airlines
søn. 5/257:10 amORD - PDX
Nonstop4h 32mUnited Airlines
Deal found 5/5![United Airlines logo]()
$231
This Booking.com deal was found by Cheapflights users on 5/4. 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.
ons. 5/145:40 pmPDX - ORD
1 stop9h 45mMultiple Airlines
søn. 5/188:14 pmORD - PDX
1 stop21h 28mMultiple Airlines
Deal found 5/4![Multiple Airlines logo]()
$232
This American Airlines deal was found by Cheapflights users on 5/6. 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.
tir. 6/2412:09 amPDX - ORD
Nonstop3h 56mAmerican Airlines
man. 6/308:22 pmORD - PDX
Nonstop4h 42mAmerican Airlines
Deal found 5/6![American Airlines logo]()
$236
This Cheapflightsfares deal was found by Cheapflights users on 5/5. 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.
lør. 5/3112:30 pmPDX - MDW
1 stop6h 23mFrontier
man. 6/26:25 amMDW - PDX
1 stop8h 30mFrontier
Deal found 5/5![Frontier logo]()
$238
This Southwest deal was found by Cheapflights users on 5/5. 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.
ons. 8/2010:40 amPDX - ORD
2 stops10h 25mSouthwest
tir. 8/267:00 amORD - PDX
1 stop11h 05mSouthwest
Deal found 5/5![Southwest logo]()
$245
This FlightHub deal was found by Cheapflights users on 5/6. 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.
tor. 9/116:05 amPDX - ORD
1 stop15h 48mFrontier
søn. 9/149:57 pmORD - PDX
1 stop21h 55mFrontier
Deal found 5/6![Frontier logo]()
$280
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 maj 6, 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
tor. 7/31
2:35 pm-11:43 pm
1 stop7h 08m
Chicago O'Hare Intl
man. 8/4
8:51 pm-10:15 am
1 stop15h 24m
$222
PortlandChicago
PDX - ORD
PDXORD
Portland
ons. 7/2
5:35 pm-11:39 pm
Nonstop4h 04m
Chicago O'Hare Intl
lør. 7/12
7:00 am-9:25 am
Nonstop4h 25m
$223
PortlandChicago
PDX - MDW
PDXMDW
Portland
tir. 6/10
12:52 am-8:44 am
1 stop5h 52m
Chicago Midway
fre. 6/13
7:21 pm-11:32 pm
1 stop6h 11m
$223
PortlandChicago
PDX - ORD
PDXORD
Portland
ons. 5/28
12:40 am-8:24 am
1 stop5h 44m
Chicago O'Hare Intl
tir. 6/3
2:25 pm-8:52 pm
1 stop8h 27m
$225
PortlandChicago
PDX - ORD
PDXORD
Portland
tor. 5/22
2:12 pm-8:25 pm
Nonstop4h 13m
Chicago O'Hare Intl
søn. 5/25
7:10 am-9:42 am
Nonstop4h 32m
$231
PortlandChicago
PDX - ORD
PDXORD
Portland
ons. 5/14
5:40 pm-5:25 am
1 stop9h 45m
Chicago O'Hare Intl
søn. 5/18
8:14 pm-3:42 pm
1 stop21h 28m
$232
PortlandChicago
PDX - MDW
PDXMDW
Portland
ons. 9/10
6:00 am-12:00 pm
Nonstop4h 00m
Chicago Midway
søn. 9/14
8:20 am-12:40 pm
1 stop6h 20m
$233
PortlandChicago
PDX - ORD
PDXORD
Portland
tor. 6/26
5:35 pm-11:39 pm
Nonstop4h 04m
Chicago O'Hare Intl
fre. 7/4
7:00 am-9:25 am
Nonstop4h 25m
$234
PortlandChicago
PDX - ORD
PDXORD
Portland
tir. 6/24
12:09 am-6:05 am
Nonstop3h 56m
Chicago O'Hare Intl
man. 6/30
8:22 pm-11:04 pm
Nonstop4h 42m
$236
PortlandChicago
PDX - MDW
PDXMDW
Portland
lør. 5/31
12:30 pm-8:53 pm
1 stop6h 23m
Chicago Midway
man. 6/2
6:25 am-12:55 pm
1 stop8h 30m
$238
Showing 1-10 of 29 results
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 May.
| 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 Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy- | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Portland-Chicago flights, users find the pricing of CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on Portland-Chicago flight deals on Cheapflights vs. CheapOair >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 CheapOair the most. CheapOair 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]()
United Airlines
![Alaska Airlines]()
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.
![Spirit Airlines]()
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.
Airports
Our travel experts
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 May 2, 2025.
Booking 77 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 maj 6, 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 39% 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 May 5, 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.
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 maj 6, 2025.
The most flights from PDX to CHI are scheduled on a Monday (27 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (23 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 maj 6, 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.
Comfort
7.9
Boarding
8.1
Crew
8.5
Entertainment
7.1
Overall
8.0
Food
7.1
Reviews
1 / 20
10.0
ExcellentJames,Apr 2025
LAX - SFO
Comfort
7.9
Boarding
8.1
Crew
8.5
Entertainment
7.1
Overall
8.0
Food
7.1
Reviews
1 / 20
10.0
ExcellentJames,Apr 2025
LAX - SFO
Comfort
7.9
Boarding
8.1
Crew
8.5
Entertainment
7.1
Overall
8.0
Food
7.1
Reviews
1 / 20
10.0
ExcellentJames,Apr 2025
LAX - SFO
Comfort
7.9
Boarding
8.1
Crew
8.5
Entertainment
7.1
Overall
8.0
Food
7.1
Reviews
1 / 20
10.0
ExcellentJames,Apr 2025
LAX - SFO
Comfort
7.9
Boarding
8.1
Crew
8.5
Entertainment
7.1
Overall
8.0
Food
7.1
Reviews
1 / 20
10.0
ExcellentJames,Apr 2025
LAX - SFO
Comfort
7.9
Boarding
8.1
Crew
8.5
Entertainment
7.1
Overall
8.0
Food
7.1
Reviews
1 / 20
10.0
ExcellentJames,Apr 2025
LAX - SFO
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.
Traveling to a place near Portland?
Book flights to Portland if you plan to visit one of these locationsMerrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton
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 Chicago
See prices for flight routes from nearby airports that may be better suited for you.
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 maj 6, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$82 | Average$133 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$108 | Average$233 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$123 | Average$343 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$185 | Average$340 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$202 | Average$298 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$211 | Average$339 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$211 | Average$395 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$249 | Average$432 | FlexibilityNo cancel fee | On-time63% |