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Illinois

$78+ 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 8/14. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
May 5 — May 121
Mon 5/5
Mon 5/12
1 adult, Economy
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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 April 30, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$174
(Alaska Airlines)

One-way from

$78
(Southwest)

Popular in

March

Cheapest in

January

Average price

$342

Good round-trip deal

$358 or less

Good one-way deal

$170 or less
Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Portland-Chicago (CHI) flights.
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From Oregon to Illinois
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One-way flight from Oregon to Illinois
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Highest demand for flights based on searches. 10% potential increase in price ($38 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Oregon to Illinois.
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Price to beat on a one-way flight from Oregon to Illinois.
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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 April 30, 2025.

This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1011:40 pmBOI - MDW
1 stop9h 01mDelta
Tue 6/179:21 amMDW - BOI
1 stop5h 34mDelta
Deal found 4/29$175
This Delta deal was found by Cheapflights users on 4/28. 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.
Wed 5/211:50 pmBOI - ORD
1 stop9h 09mDelta
Wed 6/116:15 pmORD - BOI
1 stop6h 44mDelta
Deal found 4/28$175
This United Airlines deal was found by Cheapflights users on 4/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1712:27 pmBOI - ORD
Nonstop3h 33mUnited Airlines
Fri 9/198:45 amORD - BOI
Nonstop3h 46mUnited Airlines
Deal found 4/28$189
This CheapOair deal was found by Cheapflights users on 4/28. 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.
Sun 5/182:27 pmBOI - MDW
1 stop27h 41mFrontier
Sat 5/242:44 pmMDW - BOI
1 stop22h 07mFrontier
Deal found 4/28$207
This Alaska Airlines deal was found by Cheapflights users on 4/29. 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.
Fri 5/305:39 pmBOI - ORD
1 stop11h 01mAlaska Airlines
Mon 6/28:00 amORD - BOI
1 stop8h 06mAlaska Airlines
Deal found 4/29$210
This United Airlines deal was found by Cheapflights users on 4/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/112:12 pmPDX - STL
1 stop6h 33mUnited Airlines
Mon 6/164:32 pmSTL - PDX
1 stop8h 03mUnited Airlines
Deal found 4/29$227
This CheapOair deal was found by Cheapflights users on 4/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/306:35 amPDX - STL
1 stop25h 34mFrontier
Mon 6/27:24 pmSTL - PDX
1 stop6h 55mFrontier
Deal found 4/29$228
This American Airlines deal was found by Cheapflights users on 4/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/213:24 pmPDX - ORD
Nonstop4h 05mAmerican Airlines
Tue 5/278:00 amORD - PDX
Nonstop4h 24mAmerican Airlines
Deal found 4/28$231
This Gotogate deal was found by Cheapflights users on 4/29. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/111:37 pmPDX - ORD
1 stop13h 48mMultiple Airlines
Thu 5/158:14 pmORD - PDX
1 stop21h 28mMultiple Airlines
Deal found 4/29$232
This Alaska Airlines deal was found by Cheapflights users on 4/28. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/68:45 pmPDX - ORD
1 stop7h 20mAlaska Airlines
Wed 5/79:00 amORD - PDX
1 stop8h 15mAlaska Airlines
Deal found 4/28$233
This Delta deal was found by Cheapflights users on 4/28. 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.
Sat 5/311:21 pmPDX - ORD
1 stop8h 38mDelta
Fri 6/137:20 pmORD - PDX
1 stop6h 19mDelta
Deal found 4/28$234
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
Thu 5/85:40 pmPDX - ORD
1 stop9h 45mSpirit Airlines
Fri 5/1611:50 amORD - PDX
1 stop6h 55mSpirit Airlines
Deal found 4/28$235

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 April 30, 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 - MDW

BOIMDW

Boise Air Term. Gowen Fld

Tue 6/10

11:40 pm-9:41 am

1 stop9h 01m

Chicago Midway

Tue 6/17

9:21 am-1:55 pm

1 stop5h 34m

$175

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Wed 5/21

1:50 pm-11:59 pm

1 stop9h 09m

Chicago O'Hare Intl

Tue 5/27

5:40 pm-12:22 am

1 stop7h 42m

$175

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Wed 9/17

12:27 pm-5:00 pm

Nonstop3h 33m

Chicago O'Hare Intl

Fri 9/19

8:45 am-11:31 am

Nonstop3h 46m

$189

BoiseChicago

BOI - MDW

BOIMDW

Boise Air Term. Gowen Fld

Sun 5/18

2:27 pm-7:08 pm

1 stop27h 41m

Chicago Midway

Sat 5/24

2:44 pm-11:51 am

1 stop22h 07m

$207

BoiseChicago

BOI - ORD

BOIORD

Boise Air Term. Gowen Fld

Fri 5/30

5:39 pm-5:40 am

1 stop11h 01m

Chicago O'Hare Intl

Mon 6/2

8:00 am-3:06 pm

1 stop8h 06m

$210

PortlandSt. Louis

PDX - STL

PDXSTL

Portland

Tue 6/3

11:59 pm-8:59 am

1 stop7h 00m

Lambert-St Louis

Fri 6/6

5:29 pm-12:36 am

1 stop9h 07m

$227

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 5/21

3:24 pm-9:29 pm

Nonstop4h 05m

Chicago O'Hare Intl

Tue 5/27

8:00 am-10:24 am

Nonstop4h 24m

$231

PortlandSt. Louis

PDX - STL

PDXSTL

Portland

Fri 5/16

6:20 am-9:59 am

1 stop25h 39m

Lambert-St Louis

Sat 5/24

7:55 pm-12:17 am

1 stop6h 22m

$231

PortlandChicago

PDX - ORD

PDXORD

Portland

Sun 5/11

1:37 pm-5:25 am

1 stop13h 48m

Chicago O'Hare Intl

Thu 5/15

8:14 pm-3:42 pm

1 stop21h 28m

$232

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 7/2

6:39 pm-6:12 am

1 stop9h 33m

Chicago O'Hare Intl

Tue 7/8

11:50 am-5:44 pm

1 stop7h 54m

$233

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 $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 April 30, 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 April 30, 2025.

The most flights from USOR to USIL are scheduled on a Tuesday (24 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (6 on average).

Rainfall in Illinois by month

Plan your trip to Illinois by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Illinois ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Illinois when rainfall is around 1.7 in.

Temperature in Illinois by month

Plan your trip to Illinois by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Illinois, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 30, 2025.
See what other customers who have flown with Alaska Airlines, Southwest and Delta from Oregon to Illinois have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,961 reviews

Food

7.1

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,961 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Food

7.1

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,295 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Food

7.1

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,929 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Food

7.1

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,405 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Food

7.1

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Food

7.1

Overall

8.0

Comfort

7.9

Boarding

8.2

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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.

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

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $78. Users have also found prices from $78 and $87 on United Airlines and Alaska 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 $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

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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 April 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$82Average$131FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$260FlexibilityNo cancel feeOn-time62%
DeltaCheapest$123Average$394FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$185Average$475FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$201Average$488FlexibilityNo cancel feeOn-time71%
Hawaiian AirlinesCheapest$202Average$362FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$214Average$528FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$249Average$445FlexibilityNo cancel feeOn-time63%

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