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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — CHI
Mar 2 — Mar 91
Mon 3/2
Mon 3/9
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 January 31, 2026.

This Alaska Airlines deal was found by Cheapflights users on 1/30. 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.
Tue 4/77:03 am
PDX
-
ORD
Nonstop4h 10m
Alaska Airlines
Tue 4/143:22 pm
ORD
-
PDX
1 stop8h 16m
Alaska Airlines
Deal found 1/30$217
This Southwest deal was found by Cheapflights users on 1/30. 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.
Tue 2/247:25 am
PDX
-
MDW
1 stop7h 50m
Southwest
Tue 3/245:10 pm
MDW
-
PDX
1 stop9h 05m
Southwest
Deal found 1/30$217
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:14 pm
PDX
-
ORD
1 stop10h 25m
Frontier
Thu 4/2310:55 am
ORD
-
PDX
1 stop26h 08m
Frontier
Deal found 1/30$220
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/612:04 pm
PDX
-
ORD
1 stop10h 53m
Frontier
Mon 3/98:55 pm
ORD
-
PDX
2 stops38h 03m
Frontier
Deal found 1/28$221
This CheapOair deal was found by Cheapflights users on 1/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:48 am
PDX
-
ORD
1 stop20h 02m
Frontier
Mon 4/2710:55 am
ORD
-
PDX
1 stop28h 07m
Frontier
Deal found 1/30$222
This Southwest deal was found by Cheapflights users on 1/30. 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.
Tue 2/247:25 am
PDX
-
MDW
1 stop7h 50m
Southwest
Tue 3/175:45 am
MDW
-
PDX
2 stops10h 45m
Southwest
Deal found 1/30$222
This Southwest deal was found by Cheapflights users on 1/30. 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 2/266:10 am
PDX
-
MDW
1 stop10h 30m
Southwest
Sat 2/288:30 pm
MDW
-
PDX
Nonstop4h 30m
Southwest
Deal found 1/30$223
This United Airlines deal was found by Cheapflights users on 1/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1711:59 pm
PDX
-
ORD
Nonstop3h 54m
United Airlines
Fri 2/207:59 pm
ORD
-
PDX
Nonstop4h 41m
United Airlines
Deal found 1/30$224
This Southwest deal was found by Cheapflights users on 1/30. 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.
Wed 4/297:55 pm
PDX
-
MDW
1 stop7h 05m
Southwest
Sat 5/21:55 pm
MDW
-
PDX
1 stop6h 50m
Southwest
Deal found 1/30$224
This Frontier deal was found by Cheapflights users on 1/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:14 pm
PDX
-
ORD
1 stop10h 25m
Frontier
Wed 4/229:18 pm
ORD
-
PDX
1 stop13h 41m
Frontier
Deal found 1/30$225
This Kiwi.com deal was found by Cheapflights users on 1/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/912:52 pm
PDX
-
ORD
1 stop15h 16m
Multiple Airlines
Wed 3/188:58 pm
ORD
-
PDX
2 stops40h 11m
Multiple Airlines
Deal found 1/30$226
This Delta deal was found by Cheapflights users on 1/30. 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 2/211:53 pm
PDX
-
ORD
1 stop5h 37m
Delta
Thu 2/262:20 pm
ORD
-
PDX
1 stop8h 35m
Delta
Deal found 1/30$227

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 January 31, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$217
(Delta)

One-way from

$80
(Frontier)

Popular in

March

Cheapest in

August

Average price

$302

Good round-trip deal

$318 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. 5% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 31, 2026.
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

Wed 5/6

1:25 pm-9:18 pm

1 stop5h 53m

Chicago O'Hare Intl

Tue 5/12

6:59 pm-11:41 pm

1 stop6h 42m

$217

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 4/16

1:35 pm-11:59 pm

1 stop8h 24m

Chicago O'Hare Intl

Tue 4/21

2:09 pm-4:50 pm

Nonstop4h 41m

$217

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 2/26

11:59 pm-5:53 am

Nonstop3h 54m

Chicago O'Hare Intl

Thu 3/5

4:40 pm-7:14 pm

Nonstop4h 34m

$217

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 3/6

5:20 am-11:15 am

Nonstop3h 55m

Chicago Midway

Mon 3/9

10:20 pm-12:45 am

Nonstop4h 25m

$217

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 3/14

1:36 pm-11:56 pm

1 stop8h 20m

Chicago O'Hare Intl

Wed 3/18

2:09 pm-4:50 pm

Nonstop4h 41m

$217

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 4/14

10:55 pm-9:56 am

1 stop9h 01m

Chicago Midway

Sat 4/18

2:12 pm-8:05 pm

1 stop7h 53m

$217

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 3/5

11:55 pm-5:45 am

Nonstop3h 50m

Chicago Midway

Mon 3/9

10:20 pm-12:45 am

Nonstop4h 25m

$217

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 3/13

11:55 pm-5:45 am

Nonstop3h 50m

Chicago Midway

Sun 3/15

9:40 pm-12:05 am

Nonstop4h 25m

$217

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 4/29

7:55 pm-5:00 am

1 stop7h 05m

Chicago Midway

Sat 5/2

1:55 pm-6:45 pm

1 stop6h 50m

$224

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 4/16

4:15 pm-12:30 am

1 stop6h 15m

Chicago O'Hare Intl

Sun 4/19

9:25 pm-11:58 pm

Nonstop4h 33m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

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, December is the cheapest month in which you can book a flight from Oregon to Chicago (average of $120). Flying from Oregon to Chicago in November is currently the most expensive (average of $236). 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 January 31, 2026.

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 20% versus a flight in the evening.

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 January 24, 2026.

Travelers seeking maximum savings on their Oregon to Chicago flight should consider departing on Tuesday evenings 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 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 January 31, 2026.

The most flights from USOR to CHI are scheduled on a Friday (18 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (11 on average).

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 3h 54m. 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 $82 while deals on Southwest start at $85 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 Portland - Chicago Midway or Boise Air Term. Gowen Fld - Chicago O'Hare Intl.

  • 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 (92%), Qatar Airways (88%) and United Airlines (86%).

  • What are the cheapest flights from Oregon to Chicago?

    Looking for the cheapest flight from Oregon to Chicago? While on average our users pay $920, our data indicates the cheapest price to be $108. The most popular route (Portland - Chicago O'Hare Intl), is priced around $197.

  • 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, December is the cheapest month in which you can book a flight from Oregon to Chicago (average of $120). Flying from Oregon to Chicago in November is currently the most expensive (average of $236). 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.
Dallas/Fort Worth to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Newark to O'Hare Intl flights
Baltimore to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Boston to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Seattle to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Denver to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Dallas/Fort Worth to Midway flights
Minneapolis to O'Hare Intl flights
Ontario to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Newark to Midway flights
Austin to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Los Angeles to Midway flights
Dulles Intl to Midway flights
Orlando to O'Hare Intl flights
Love Field to O'Hare Intl flights
Atlanta to Midway flights
Minneapolis to Midway flights
Philadelphia to Midway flights
Charlotte to O'Hare Intl flights
Baltimore to Midway flights
Newark to St. Louis flights
LaGuardia to Midway flights
Tampa to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Raleigh to Midway flights
George Bush Intcntl to O'Hare Intl flights
San Jose to O'Hare Intl flights
Hartford to O'Hare Intl flights
Kansas City to O'Hare Intl flights
San Diego to O'Hare Intl flights
San Francisco to Midway flights
Nashville to O'Hare Intl flights
Greensboro to O'Hare Intl flights
Hobby to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Sacramento to O'Hare Intl flights
Dallas/Fort Worth to St. Louis flights
Portland 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 January 31, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$86Average$243FlexibilityNo cancel feeOn-time62%
DeltaCheapest$99Average$355FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$119Average$194FlexibilityNo cancel feeOn-time65%
Hawaiian AirlinesCheapest$125Average$323FlexibilityNo cancel feeOn-time85%
SouthwestCheapest$179Average$414FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$184Average$419FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$196Average$486FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$217Average$400FlexibilityNo cancel feeOn-time75%

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.