HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$80+ Cheap flights from Oregon 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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — CHI
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Oregon 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.

Cheap flight deals from Oregon to Chicago

Keep the following information in mind while searching for Oregon to Chicago flight deals. Data was last updated July 31, 2025.

Round-trip from

$198
(Alaska Airlines)

One-way from

$80
(Booking.com)

Popular in

March

Cheapest in

January

Average price

$317

Good round-trip deal

$250 or less

Good one-way deal

$171 or less
From Oregon to Chicago (CHI)
Search Deals
One-way flight from Oregon to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals
Price to beat on a round-trip flight from Oregon to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Oregon to Chicago (CHI).
Search Deals

Find flight deals from Oregon to Chicago

Cheapest flights from Oregon to Chicago
Explore the most affordable flight options available from Oregon to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

This Hawaiian Airlines deal was found by Cheapflights users on 7/30. 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.
Sat 8/305:50 pmPDX - ORD
Nonstop4h 09mHawaiian Airlines
Mon 9/17:00 amORD - PDX
Nonstop4h 25mHawaiian Airlines
Deal found 7/30$198
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/268:04 pmPDX - ORD
1 stop6h 45mSpirit Airlines
Wed 10/16:00 amORD - PDX
1 stop7h 12mSpirit Airlines
Deal found 7/29$201
This Alaska Airlines deal was found by Cheapflights users on 7/29. 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 9/65:50 pmPDX - ORD
Nonstop4h 14mAlaska Airlines
Tue 9/235:45 pmORD - PDX
1 stop7h 02mAlaska Airlines
Deal found 7/29$207
This Southwest deal was found by Cheapflights users on 7/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/46:10 amPDX - MDW
Nonstop4h 00mSouthwest
Wed 9/108:30 pmMDW - PDX
Nonstop4h 15mSouthwest
Deal found 7/30$207
This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/205:45 amBOI - ORD
2 stops11h 22mDelta
Sat 8/237:15 amORD - BOI
1 stop6h 51mDelta
Deal found 7/30$222
This CheapOair deal was found by Cheapflights users on 7/28. 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 8/127:01 pmPDX - ORD
1 stop27h 31mMultiple Airlines
Mon 8/186:00 amORD - PDX
1 stop14h 57mMultiple Airlines
Deal found 7/28$223
This Alaska Airlines deal was found by Cheapflights users on 7/30. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/117:13 amBOI - ORD
1 stop15h 46mAlaska Airlines
Thu 10/166:00 amORD - BOI
1 stop8h 10mAlaska Airlines
Deal found 7/30$224
This Delta deal was found by Cheapflights users on 7/28. 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 9/2611:35 pmBOI - MDW
1 stop9h 13mDelta
Tue 9/306:00 amMDW - BOI
1 stop7h 30mDelta
Deal found 7/28$225
This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/236:00 amPDX - MDW
1 stop7h 28mDelta
Sat 8/307:17 pmMDW - PDX
1 stop6h 14mDelta
Deal found 7/30$225
This Booking.com deal was found by Cheapflights users on 7/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/146:06 pmBOI - ORD
1 stop9h 44mSpirit Airlines
Mon 8/186:00 amORD - BOI
1 stop12h 11mSpirit Airlines
Deal found 7/30$227
This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2212:46 amPDX - ORD
1 stop5h 38mDelta
Sat 8/306:24 pmORD - PDX
1 stop6h 11mDelta
Deal found 7/30$232
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/116:07 amPDX - ORD
Nonstop4h 05mAmerican Airlines
Thu 9/189:40 pmORD - PDX
Nonstop4h 25mAmerican Airlines
Deal found 7/30$233

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oregon 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 31, 2025.
Use the filters below to find and compare flights from Oregon to Chicago that are best for you.

Fly from

Oregon

Fly to

Chicago

Route

Depart

Return

Price

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 8/30

5:50 pm-11:59 pm

Nonstop4h 09m

Chicago O'Hare Intl

Mon 9/1

7:00 am-9:25 am

Nonstop4h 25m

$198

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 9/26

8:04 pm-4:49 am

1 stop6h 45m

Chicago O'Hare Intl

Wed 10/1

6:00 am-11:12 am

1 stop7h 12m

$201

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 9/6

5:50 pm-12:04 am

Nonstop4h 14m

Chicago O'Hare Intl

Wed 9/24

6:20 am-1:47 pm

1 stop9h 27m

$207

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 9/4

6:10 am-12:10 pm

Nonstop4h 00m

Chicago Midway

Wed 9/10

8:30 pm-10:45 pm

Nonstop4h 15m

$207

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Wed 8/20

5:45 am-6:07 pm

2 stops11h 22m

Chicago O'Hare Intl

Sat 8/23

7:15 am-1:06 pm

1 stop6h 51m

$222

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 8/12

7:01 pm-12:32 am

1 stop27h 31m

Chicago O'Hare Intl

Mon 8/18

6:00 am-6:57 pm

1 stop14h 57m

$223

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Sat 10/11

7:13 am-11:59 pm

1 stop15h 46m

Chicago O'Hare Intl

Thu 10/16

6:00 am-1:10 pm

1 stop8h 10m

$224

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Fri 9/26

11:35 pm-9:48 am

1 stop9h 13m

Chicago Midway

Tue 9/30

6:00 am-12:30 pm

1 stop7h 30m

$225

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 8/23

6:00 am-3:28 pm

1 stop7h 28m

Chicago Midway

Sat 8/30

7:17 pm-11:31 pm

1 stop6h 14m

$225

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Thu 8/14

6:06 pm-4:50 am

1 stop9h 44m

Chicago O'Hare Intl

Mon 8/18

6:00 am-5:11 pm

1 stop12h 11m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Oregon to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Oregon 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 Oregon to Chicago

What is the cheapest month to book a flight from Oregon to Chicago?

Currently, August is the cheapest month in which you can book a flight from Oregon to Chicago (average of $245). Flying from Oregon 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 OR to CHI?

Find hourly flight availability from Oregon 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 31, 2025.

When flying from Oregon to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Oregon to Chicago

Explore weekly flight availability from Oregon 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 31, 2025.

The most flights from USOR to CHI are scheduled on a Wednesday (31 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 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 31, 2025.
Read through reviews of airlines operating flights from Oregon to Chicago, such as Alaska Airlines, Southwest, and Delta. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,241 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,980 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Hawaiian Airlines
7.8
Good
2,611 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,896 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Entertainment

7.1

Comfort

7.8

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

Related info for your journey

Find useful and relevant information for your journey from Oregon to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $80. Alaska Airlines flights start at $98 while deals on American Airlines start at $99 one-way.

  • What are the most popular routes from Oregon to Chicago?

    The most popular route from Oregon to Chicago is Portland - Chicago O'Hare Intl. You may also consider Boise Air Term. Gowen Fld - Chicago O'Hare Intl or Portland - Chicago Midway.

  • What are the most reliable airlines from Oregon to Chicago?

    The top 3 most reliable airlines when flying from Oregon to Chicago are Brussels Airlines (87%), SWISS (86%) and Finnair (82%).

  • What are the cheapest flights from Oregon to Chicago?

    Looking for the cheapest flight from Oregon to Chicago? While on average our users pay $904, our data indicates the cheapest price to be $98. The most popular route (Portland - Chicago O'Hare Intl), is priced around $168.

  • Can I find deals for flights from Oregon to Chicago that include hotel bookings?

    Yes. In addition to deals on Oregon to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oregon to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oregon to Chicago.

  • Can I find deals for business class flights from Oregon to Chicago?

    Yes. Cheapflights offers flight deals from Oregon 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 Oregon to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Oregon to Chicago (average of $245). Flying from Oregon 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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 Oregon to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to O'Hare Intl flights
Newark to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Seattle to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Newark to Midway flights
John F Kennedy Intl to Midway flights
Boston to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Philadelphia to O'Hare Intl flights
LaGuardia to Midway flights
Ontario to O'Hare Intl flights
Austin to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Dulles Intl to Midway flights
Atlanta to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Denver to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Baltimore to Midway flights
Hobby to Midway flights
Fort Lauderdale to O'Hare Intl flights
Love Field to O'Hare Intl flights
Burbank to O'Hare Intl flights
Miami to O'Hare Intl flights
Charlotte to O'Hare Intl flights
San Francisco to Midway flights
Orlando to O'Hare Intl flights
San Diego to O'Hare Intl flights
Hobby to O'Hare Intl flights
San Jose to O'Hare Intl flights
Portland to O'Hare Intl flights
Los Angeles to Midway flights
Reagan-National to Midway flights
Minneapolis to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Philadelphia to Midway flights
Tampa to O'Hare Intl flights
Nashville to O'Hare Intl flights
Boston to Midway flights
Oakland to O'Hare Intl flights
Newark to St. Louis flights
Cleveland to O'Hare Intl flights
Minneapolis to Midway flights

Top 8 airlines flying from Oregon to Chicago

Discover the top 8 airlines that operate flights from Oregon 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 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$96Average$176FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$219FlexibilityNo cancel feeOn-time62%
DeltaCheapest$123Average$360FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$178Average$333FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$187Average$441FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$218Average$328FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$224Average$472FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$249Average$443FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.