HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Illinois

$74+ Cheap flights from Oregon to Illinois

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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Oregon to Illinois 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 Illinois

Keep the following information in mind while searching for Oregon to Illinois flight deals. Data was last updated September 15, 2025.

Round-trip from

$196
(Kiwi.com)

One-way from

$74
(United Airlines)

Popular in

March

Cheapest in

January

Average price

$303

Good round-trip deal

$312 or less

Good one-way deal

$169 or less
From Oregon to Illinois
Search Deals
One-way flight from Oregon to Illinois
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($33 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 September 2025
Search Deals
Price to beat on a round-trip flight from Oregon to Illinois.
Search Deals
Price to beat on a one-way flight from Oregon to Illinois.
Search Deals

Find flight deals from Oregon to Illinois

Cheapest flights from Oregon to Illinois
Explore the most affordable flight options available from Oregon to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Frontier deal was found by Cheapflights users on 9/12. 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.
Thu 10/2312:43 pmPDX - MDW
1 stop9h 53mFrontier
Sun 10/269:26 pmMDW - PDX
2 stops16h 22mFrontier
Deal found 9/12$196
This Expedia deal was found by Cheapflights users on 9/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/210:55 pmPDX - ORD
Nonstop4h 05mAlaska Airlines
Mon 10/67:00 amORD - PDX
Nonstop4h 32mAlaska Airlines
Deal found 9/13$197
This Booking.com deal was found by Cheapflights users on 9/13. 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.
Mon 10/2012:43 pmPDX - MDW
1 stop9h 41mFrontier
Thu 10/236:24 pmMDW - PDX
1 stop19h 24mFrontier
Deal found 9/13$198
This Frontier deal was found by Cheapflights users on 9/14. 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.
Tue 10/1412:43 pmPDX - ORD
1 stop9h 10mFrontier
Tue 10/217:15 amORD - PDX
1 stop6h 33mFrontier
Deal found 9/14$199
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Sat 11/812:52 pmPDX - ORD
1 stop9h 20mFrontier
Wed 11/127:20 amORD - PDX
1 stop30h 36mFrontier
Deal found 9/14$200
This Delta deal was found by Cheapflights users on 9/13. 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.
Thu 10/210:50 pmPDX - ORD
1 stop7h 15mDelta
Tue 10/76:05 pmORD - PDX
1 stop6h 35mDelta
Deal found 9/13$201
This Flightnetwork deal was found by Cheapflights users on 9/13. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2611:14 amPDX - ORD
1 stop9h 26mMultiple Airlines
Mon 9/296:15 amORD - PDX
1 stop6h 56mMultiple Airlines
Deal found 9/13$202
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/112:07 pmPDX - ORD
1 stop7h 25mSpirit Airlines
Fri 10/36:15 amORD - PDX
1 stop6h 56mSpirit Airlines
Deal found 9/14$203
This Frontier deal was found by Cheapflights users on 9/13. 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.
Fri 10/1712:43 pmPDX - ORD
1 stop10h 16mFrontier
Mon 10/206:50 amORD - PDX
1 stop6h 58mFrontier
Deal found 9/13$204
This Frontier deal was found by Cheapflights users on 9/14. 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.
Wed 10/17:15 amPDX - MDW
2 stops21h 56mFrontier
Fri 10/34:48 pmMDW - PDX
1 stop9h 24mFrontier
Deal found 9/14$204
This Frontier deal was found by Cheapflights users on 9/13. 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.
Mon 10/2012:43 pmPDX - ORD
1 stop10h 16mFrontier
Mon 10/276:50 amORD - PDX
1 stop6h 58mFrontier
Deal found 9/13$205
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Fri 10/3111:00 pmPDX - ORD
Nonstop4h 01mHawaiian Airlines
Sat 11/82:05 pmORD - PDX
Nonstop4h 36mHawaiian Airlines
Deal found 9/14$206

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oregon to Illinois 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 September 15, 2025.
Use the filters below to find and compare flights from Oregon to Illinois that are best for you.

Fly from

Oregon

Fly to

Illinois

Route

Depart

Return

Price

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 1/16

7:00 am-1:04 pm

Nonstop4h 04m

Chicago O'Hare Intl

Mon 1/19

7:45 am-1:46 pm

1 stop8h 01m

$207

RedmondChicago

RDM - ORD

RDMORD

Bend/Redmond

Sat 11/8

7:00 am-5:18 pm

1 stop8h 18m

Chicago O'Hare Intl

Tue 11/11

6:13 pm-10:53 pm

1 stop6h 40m

$234

EugeneChicago

EUG - ORD

EUGORD

Eugene

Sat 12/6

7:00 am-5:18 pm

1 stop8h 18m

Chicago O'Hare Intl

Fri 12/12

6:13 pm-11:11 pm

1 stop6h 58m

$235

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 10/22

11:00 pm-5:01 am

Nonstop4h 01m

Chicago O'Hare Intl

Wed 10/29

2:54 pm-8:46 pm

1 stop7h 52m

$241

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 10/28

7:00 am-1:09 pm

Nonstop4h 09m

Chicago O'Hare Intl

Tue 11/4

2:54 pm-8:46 pm

1 stop7h 52m

$241

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 11/7

11:00 pm-5:01 am

Nonstop4h 01m

Chicago O'Hare Intl

Sun 11/9

6:00 am-10:32 am

1 stop6h 32m

$243

PortlandChicago

PDX - ORD

PDXORD

Portland

Mon 10/20

7:00 am-1:08 pm

Nonstop4h 08m

Chicago O'Hare Intl

Wed 10/22

7:50 pm-10:25 pm

Nonstop4h 35m

$244

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 10/15

11:00 pm-5:01 am

Nonstop4h 01m

Chicago O'Hare Intl

Thu 10/23

7:00 am-9:32 am

Nonstop4h 32m

$244

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Tue 10/28

10:40 am-9:02 pm

1 stop9h 22m

Chicago O'Hare Intl

Wed 10/29

8:45 am-11:39 am

Nonstop3h 54m

$245

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Tue 11/4

2:31 pm-8:58 pm

1 stop5h 27m

Chicago O'Hare Intl

Wed 11/12

8:45 am-11:39 am

Nonstop3h 54m

$245

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

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

Best time to book a flight from Oregon to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois 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 Illinois

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

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

Find hourly flight availability from Oregon to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Oregon to Illinois as you normally would.

Weekly flight availability from Oregon to Illinois

Explore weekly flight availability from Oregon to Illinois. 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 September 15, 2025.

The most flights from USOR to USIL are scheduled on a Friday (32 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (23 on average).

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated September 15, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest, and Delta from Oregon to Illinois to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Southwest
8.0
Very good
4,242 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Delta
8.0
Very good
7,954 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,929 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.0

Crew

8.5

Boarding

8.1

Comfort

7.8

Overall

8.0

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

Related info for your journey

Find useful and relevant information for your journey from Oregon to Illinois. 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 Illinois?

    A quick flight from Oregon to Illinois can take about 4h 01m. Hawaiian Airlines provides one of the quickest options available for as low as $243. Airlines will cover a distance of 1733 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $74. Users have also found prices from $93 and $100 on Southwest and Delta, respectively.

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

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

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

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

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

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

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

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 Illinois

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to John F Kennedy Intl flights
John F Kennedy Intl to Los Angeles flights
Dallas/Fort Worth to Las Vegas flights
LaGuardia to Dallas/Fort Worth flights
John F Kennedy Intl to Las Vegas flights
Dallas/Fort Worth to John F Kennedy Intl flights
John F Kennedy Intl to O'Hare Intl flights
John F Kennedy Intl to Miami flights
Dallas/Fort Worth to O'Hare Intl flights
Newark to Fort Lauderdale flights
San Francisco to John F Kennedy Intl flights
Dallas/Fort Worth to LaGuardia flights
LaGuardia to O'Hare Intl flights
Newark to Las Vegas flights
Seattle to Las Vegas flights
O'Hare Intl to LaGuardia flights
Newark to O'Hare Intl flights
LaGuardia to Fort Lauderdale flights
Newark to Miami flights
Los Angeles to Newark flights
LaGuardia to Miami flights
Seattle to Los Angeles flights
O'Hare Intl to Las Vegas flights
John F Kennedy Intl to Dallas/Fort Worth flights
Dallas/Fort Worth to Los Angeles flights
O'Hare Intl to John F Kennedy Intl flights
Los Angeles to Dallas/Fort Worth flights
Newark to Dallas/Fort Worth flights
John F Kennedy Intl to Atlanta flights
O'Hare Intl to Newark flights
John F Kennedy Intl to San Francisco flights
Los Angeles to Seattle flights
O'Hare Intl to Dallas/Fort Worth flights
Seattle to Dallas/Fort Worth flights
Dallas/Fort Worth to Denver flights
Dallas/Fort Worth to Newark flights
Dallas/Fort Worth to Seattle flights
San Francisco to Las Vegas flights
John F Kennedy Intl to Orlando flights
Los Angeles to San Francisco flights
Los Angeles to O'Hare Intl flights
Los Angeles to LaGuardia flights
San Francisco to Newark flights
Newark to Los Angeles flights
Atlanta to LaGuardia flights
Newark to San Francisco flights
Dulles Intl to Dallas/Fort Worth flights
John F Kennedy Intl to Fort Lauderdale flights
LaGuardia to Los Angeles flights
Newark to Orlando flights

Top 8 airlines flying from Oregon to Illinois

Discover the top 8 airlines that operate flights from Oregon to Illinois. 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$93Average$200FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$268FlexibilityNo cancel feeOn-time62%
DeltaCheapest$123Average$396FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$125Average$324FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$195Average$464FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$200Average$440FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$226Average$479FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$233Average$431FlexibilityNo 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.