HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$87+ 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — CHI
ene. 16 — ene. 231
vie. 1/16
vie. 1/23
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

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 diciembre 17, 2025.

This Alaska Airlines deal was found by Cheapflights users on 12/15. 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. 12/2511:00 pmPDX - ORD
Nonstop4h 02mAlaska Airlines
lun. 1/263:35 pmORD - PDX
1 stop7h 12mAlaska Airlines
Deal found 12/15$237
This Kiwi.com deal was found by Cheapflights users on 12/14. 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.
mié. 12/243:59 pmPDX - ORD
2 stops20h 18mFrontier
jue. 1/152:30 pmORD - PDX
1 stop22h 34mFrontier
Deal found 12/14$246
This Delta deal was found by Cheapflights users on 12/15. 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.
jue. 12/251:45 pmPDX - ORD
1 stop5h 51mDelta
jue. 1/222:20 pmORD - PDX
1 stop6h 30mDelta
Deal found 12/15$247
This Kiwi.com deal was found by Cheapflights users on 12/15. 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.
mié. 12/243:59 pmPDX - ORD
2 stops20h 18mFrontier
dom. 1/259:38 pmORD - PDX
1 stop15h 40mFrontier
Deal found 12/15$249
This Alaska Airlines deal was found by Cheapflights users on 12/15. 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. 12/2511:00 pmPDX - ORD
Nonstop4h 02mAlaska Airlines
vie. 1/239:00 amORD - PDX
1 stop9h 44mAlaska Airlines
Deal found 12/15$253
This Frontier deal was found by Cheapflights users on 12/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/2312:47 pmPDX - ORD
1 stop9h 25mFrontier
jue. 1/1510:41 pmORD - PDX
1 stop13h 52mFrontier
Deal found 12/14$274
This United Airlines deal was found by Cheapflights users on 12/15. 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.
mar. 12/3012:20 pmBOI - ORD
Nonstop3h 44mUnited Airlines
mar. 1/69:15 amORD - BOI
Nonstop4h 24mUnited Airlines
Deal found 12/15$279
This Priceline deal was found by Cheapflights users on 12/15. 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.
mar. 12/2312:47 pmPDX - ORD
1 stop9h 25mFrontier
jue. 12/257:00 amORD - PDX
1 stop6h 43mFrontier
Deal found 12/15$284
This Kiwi.com deal was found by Cheapflights users on 12/15. 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.
jue. 12/2512:39 pmPDX - ORD
1 stop15h 26mMultiple Airlines
mié. 1/212:18 pmORD - PDX
2 stops22h 15mMultiple Airlines
Deal found 12/15$289
This Kiwi.com deal was found by Cheapflights users on 12/14. 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.
mié. 12/243:59 pmPDX - ORD
1 stop26h 24mFrontier
sáb. 1/176:02 pmORD - PDX
1 stop15h 21mFrontier
Deal found 12/14$296
This United Airlines deal was found by Cheapflights users on 12/15. 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.
jue. 12/2511:55 pmPDX - ORD
Nonstop4h 01mUnited Airlines
mié. 1/219:10 amORD - PDX
Nonstop4h 47mUnited Airlines
Deal found 12/15$307
This United Airlines deal was found by Cheapflights users on 12/15. 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.
mar. 12/3012:20 pmBOI - ORD
Nonstop3h 44mUnited Airlines
sáb. 1/37:42 pmORD - BOI
Nonstop4h 17mUnited Airlines
Deal found 12/15$309

Find flight deals from Oregon to Chicago

Keep the following information in mind while searching for Oregon to Chicago flight deals. Data was last updated diciembre 17, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$164
(Kiwi.com)

One-way from

$87
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$415

Good round-trip deal

$316 or less

Good one-way deal

$166 or less
Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Chicago (CHI) flights.
Search Deals
From Oregon to Chicago (CHI)
Search Deals
One-way flight from Oregon to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($25 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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

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 diciembre 17, 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

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

lun. 1/12

1:55 pm-11:50 pm

1 stop8h 55m

Chicago O'Hare Intl

jue. 1/15

9:00 am-11:42 pm

1 stop15h 42m

$228

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

mar. 1/20

7:55 pm-2:29 pm

1 stop17h 34m

Chicago O'Hare Intl

sáb. 1/24

3:44 pm-11:42 pm

1 stop8h 58m

$228

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

dom. 1/11

7:45 am-11:37 pm

1 stop14h 52m

Chicago O'Hare Intl

mié. 1/14

6:06 pm-11:59 pm

1 stop6h 53m

$228

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

mié. 1/14

1:55 pm-11:50 pm

1 stop8h 55m

Chicago O'Hare Intl

mié. 1/21

9:00 am-11:42 pm

1 stop15h 42m

$228

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

dom. 1/11

7:45 am-11:37 pm

1 stop14h 52m

Chicago O'Hare Intl

jue. 1/15

8:00 am-3:10 pm

1 stop8h 10m

$228

PortlandChicago

PDX - ORD

PDXORD

Portland

mié. 1/28

1:24 pm-9:15 pm

1 stop5h 51m

Chicago O'Hare Intl

sáb. 1/31

12:45 pm-6:55 pm

1 stop8h 10m

$232

PortlandChicago

PDX - ORD

PDXORD

Portland

sáb. 2/14

1:18 pm-9:29 pm

1 stop6h 11m

Chicago O'Hare Intl

vie. 2/20

7:59 pm-10:40 pm

Nonstop4h 41m

$233

PortlandChicago

PDX - ORD

PDXORD

Portland

sáb. 1/24

1:24 pm-9:15 pm

1 stop5h 51m

Chicago O'Hare Intl

dom. 1/25

7:50 pm-10:32 pm

Nonstop4h 42m

$233

PortlandChicago

PDX - MDW

PDXMDW

Portland

sáb. 1/10

12:30 pm-9:10 pm

1 stop6h 40m

Chicago Midway

sáb. 1/17

4:05 pm-8:30 pm

1 stop6h 25m

$236

PortlandChicago

PDX - ORD

PDXORD

Portland

jue. 1/1

5:30 am-1:20 pm

1 stop5h 50m

Chicago O'Hare Intl

sáb. 1/10

6:15 am-12:46 pm

1 stop8h 31m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

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 $120). Flying from Oregon to Chicago in March is currently the most expensive (average of $242). 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 diciembre 17, 2025.

When flying from Oregon to Chicago, 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 18% versus a flight in the morning.

What is the cheapest day to fly from Oregon to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Oregon to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Oregon to Chicago flight should consider departing on Wednesday 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.

How much does it cost to fly round-trip from Oregon to Chicago?

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.

  • How long is the flight from Oregon to Chicago?

    Departing from Oregon to Chicago will take you 5h 51m. Airlines will cover a distance of 1733 mi. This flight may include one or multiple stops.

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $72. Spirit Airlines flights start at $80 while deals on Delta start at $97 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 SWISS (89%), Air Canada (87%) and Gulf Air (87%).

  • What are the cheapest flights from Oregon to Chicago?

    Looking for the cheapest flight from Oregon to Chicago? While on average our users pay $966, our data indicates the cheapest price to be $108. The most popular route (Portland - Chicago O'Hare Intl), is priced around $200.

  • 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 $120). Flying from Oregon to Chicago in March is currently the most expensive (average of $242). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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.
John F Kennedy Intl to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Newark to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Atlanta to O'Hare Intl flights
Boston to O'Hare Intl flights
Seattle to O'Hare Intl flights
Denver to O'Hare Intl flights
Baltimore to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Los Angeles to Midway flights
Philadelphia to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Atlanta to Midway flights
Love Field to O'Hare Intl flights
LaGuardia to Midway flights
Dulles Intl to O'Hare Intl flights
Tampa to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Ontario to O'Hare Intl flights
Austin to O'Hare Intl flights
Hobby to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Minneapolis to Midway flights
Hobby to Midway flights
Denver to Midway flights
Santa Ana to O'Hare Intl flights
San Diego to O'Hare Intl flights
Orlando to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Love Field to Midway flights
Boston to Midway flights
Philadelphia to Midway flights
Miami to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Dulles Intl to Midway flights
Newark to St. Louis flights
George Bush Intcntl to Midway flights
Baltimore to Midway flights
Denver to St. Louis flights
Fort Lauderdale to Midway flights
Las Vegas to O'Hare Intl flights
Hartford to O'Hare Intl flights
Detroit to O'Hare Intl 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 diciembre 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$96Average$243FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$119Average$184FlexibilityNo cancel feeOn-time65%
DeltaCheapest$123Average$364FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$125Average$324FlexibilityNo cancel feeOn-time85%
SouthwestCheapest$179Average$415FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$194Average$489FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$217Average$405FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$223Average$408FlexibilityNo cancel feeOn-time69%

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.