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Illinois

$68+ 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 1/16. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Cheap 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 December 15, 2025.

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.
Wed 12/243:59 pmPDX - ORD
2 stops20h 18mFrontier
Thu 1/152:30 pmORD - PDX
1 stop22h 34mFrontier
Deal found 12/14$246
This Frontier deal was found by Cheapflights users on 12/13. 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.
Sun 12/2112:38 pmBOI - ORD
1 stop10h 34mFrontier
Thu 1/17:00 amORD - BOI
1 stop5h 43mFrontier
Deal found 12/13$258
This Delta deal was found by Cheapflights users on 12/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/255:50 amBOI - ORD
1 stop6h 56mDelta
Mon 1/56:15 amORD - BOI
1 stop8h 47mDelta
Deal found 12/12$272
This United Airlines deal was found by Cheapflights users on 12/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:45 pmPDX - ORD
1 stop7h 14mUnited Airlines
Mon 1/59:08 amORD - PDX
Nonstop4h 50mUnited Airlines
Deal found 12/12$273
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.
Tue 12/2312:47 pmPDX - ORD
1 stop9h 25mFrontier
Thu 1/1510:41 pmORD - PDX
1 stop13h 52mFrontier
Deal found 12/14$274
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2511:55 pmPDX - ORD
Nonstop4h 01mUnited Airlines
Sun 1/48:02 pmORD - PDX
Nonstop4h 41mUnited Airlines
Deal found 12/14$276
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2511:00 pmPDX - ORD
Nonstop4h 02mMultiple Airlines
Sun 1/47:00 amORD - PDX
1 stop6h 43mMultiple Airlines
Deal found 12/14$285
This Frontier deal was found by Cheapflights users on 12/13. 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.
Sun 12/2112:38 pmBOI - ORD
1 stop10h 34mFrontier
Sun 1/47:00 amORD - BOI
1 stop5h 43mFrontier
Deal found 12/13$292
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.
Thu 12/2512:47 pmPDX - ORD
1 stop9h 25mFrontier
Sun 1/47:00 amORD - PDX
1 stop6h 43mFrontier
Deal found 12/14$292
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.
Wed 12/243:59 pmPDX - ORD
1 stop26h 24mFrontier
Sat 1/176:02 pmORD - PDX
1 stop15h 21mFrontier
Deal found 12/14$296
This Frontier deal was found by Cheapflights users on 12/12. 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 12/2512:38 pmBOI - ORD
1 stop10h 34mFrontier
Sat 1/37:00 amORD - BOI
1 stop5h 59mFrontier
Deal found 12/12$307
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.
Thu 12/2512:47 pmPDX - ORD
1 stop9h 25mFrontier
Fri 1/21:27 pmORD - PDX
1 stop8h 23mFrontier
Deal found 12/14$307

Find flight deals from Oregon to Illinois

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

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$179
(Kiwi.com)

One-way from

$68
(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 Illinois
Search Deals
One-way flight from Oregon to Illinois
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 Illinois.
Search Deals
Price to beat on a one-way flight from Oregon to Illinois.
Search Deals

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 December 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

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Tue 1/6

3:45 pm-11:59 pm

1 stop7h 14m

Chicago O'Hare Intl

Fri 1/9

3:44 pm-11:42 pm

1 stop8h 58m

$228

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Thu 1/22

7:45 am-11:37 pm

1 stop14h 52m

Chicago O'Hare Intl

Thu 2/5

2:06 pm-8:04 pm

1 stop6h 58m

$228

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Sun 1/25

6:23 am-2:38 pm

1 stop7h 15m

Chicago O'Hare Intl

Wed 1/28

6:06 pm-11:59 pm

1 stop6h 53m

$228

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Wed 2/11

9:02 am-5:10 pm

1 stop7h 08m

Chicago O'Hare Intl

Tue 2/17

3:54 pm-10:40 pm

1 stop7h 46m

$228

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Fri 2/13

6:28 am-4:33 pm

1 stop9h 05m

Chicago O'Hare Intl

Wed 2/18

3:54 pm-11:59 pm

1 stop9h 05m

$228

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Wed 2/11

6:23 am-5:10 pm

1 stop9h 47m

Chicago O'Hare Intl

Wed 2/18

5:29 pm-11:59 pm

1 stop7h 30m

$228

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Fri 1/23

7:45 am-11:37 pm

1 stop14h 52m

Chicago O'Hare Intl

Fri 1/30

8:00 am-3:10 pm

1 stop8h 10m

$228

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Thu 2/12

12:28 pm-11:14 pm

1 stop9h 46m

Chicago O'Hare Intl

Sat 2/14

8:05 am-11:03 am

2 stops27h 58m

$233

PortlandChicago

PDX - ORD

PDXORD

Portland

Sun 1/11

11:59 pm-6:00 am

Nonstop4h 01m

Chicago O'Hare Intl

Sun 1/18

11:05 am-6:55 pm

1 stop9h 50m

$237

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 2/13

12:40 am-11:03 am

1 stop8h 23m

Chicago Midway

Tue 2/17

1:49 pm-8:30 pm

1 stop8h 41m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/13

Showing 1-10 of 60 results
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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 $120). Flying from Oregon to Illinois 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 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 December 15, 2025.

It’s optimal to fly from Oregon to Illinois in the afternoon. By choosing this option you can save up to 28% on the cost of your flight, compared to a flight at noon.

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

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

Travelers seeking maximum savings on their Oregon to Illinois 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.

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 December 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
11,451 reviews

Crew

8.5

Overall

8.0

Comfort

7.8

Entertainment

7.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Alaska Airlines
8.0
Very good
11,451 reviews
Alaska Airlines
8.0
Very good
11,451 reviews

Crew

8.5

Overall

8.0

Comfort

7.8

Entertainment

7.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Southwest
7.9
Good
4,250 reviews
Alaska Airlines
8.0
Very good
11,451 reviews

Crew

8.5

Overall

8.0

Comfort

7.8

Entertainment

7.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Delta
7.9
Good
8,007 reviews
Alaska Airlines
8.0
Very good
11,451 reviews

Crew

8.5

Overall

8.0

Comfort

7.8

Entertainment

7.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
United Airlines
7.4
Good
9,092 reviews
Alaska Airlines
8.0
Very good
11,451 reviews

Crew

8.5

Overall

8.0

Comfort

7.8

Entertainment

7.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
American Airlines
7.2
Good
11,052 reviews
Alaska Airlines
8.0
Very good
11,451 reviews

Crew

8.5

Overall

8.0

Comfort

7.8

Entertainment

7.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.

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. Alaska Airlines provides one of the quickest options available for as low as $237. 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 Frontier. According to our data, you can fly for as low as $30. Users have also found prices from $52 and $52 on Spirit Airlines and Hawaiian Airlines, 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 $120). Flying from Oregon to Illinois 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

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Alternative routes for Oregon to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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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 December 15, 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$482FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$217Average$405FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$223Average$466FlexibilityNo cancel feeOn-time69%

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