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$63+ 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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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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 October 29, 2025.

This Frontier deal was found by Cheapflights users on 10/27. 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 12/412:44 pmBOI - STL
1 stop20h 30mFrontier
Wed 12/107:43 pmSTL - BOI
1 stop17h 06mFrontier
Deal found 10/27$131
This Frontier deal was found by Cheapflights users on 10/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/612:52 pmPDX - ORD
1 stop9h 23mFrontier
Thu 12/47:00 amORD - PDX
1 stop6h 56mFrontier
Deal found 10/28$226
This American Airlines deal was found by Cheapflights users on 10/27. 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.
Fri 12/51:28 pmPDX - ORD
Nonstop4h 18mAmerican Airlines
Sat 12/69:57 amORD - PDX
Nonstop4h 41mAmerican Airlines
Deal found 10/27$227
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Tue 11/41:26 pmPDX - ORD
1 stop24h 13mFrontier
Thu 12/47:00 amORD - PDX
1 stop30h 56mFrontier
Deal found 10/28$228
This Mytrip deal was found by Cheapflights users on 10/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/23:26 pmPDX - MDW
1 stop18h 04mFrontier
Thu 11/612:30 pmMDW - PDX
1 stop25h 26mFrontier
Deal found 10/26$228
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Tue 11/111:26 pmPDX - ORD
1 stop24h 13mFrontier
Fri 11/1410:43 pmORD - PDX
2 stops39h 13mFrontier
Deal found 10/28$229
This Booking.com deal was found by Cheapflights users on 10/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/73:26 pmPDX - ORD
1 stop6h 49mFrontier
Wed 11/126:05 pmORD - PDX
1 stop19h 51mFrontier
Deal found 10/28$230
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 12/1112:51 pmPDX - ORD
1 stop9h 21mFrontier
Mon 12/156:50 amORD - PDX
1 stop11h 47mFrontier
Deal found 10/27$231
This United Airlines deal was found by Cheapflights users on 10/27. 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.
Sun 12/711:59 pmPDX - ORD
Nonstop3h 53mUnited Airlines
Tue 12/96:00 amORD - PDX
1 stop8h 12mUnited Airlines
Deal found 10/27$233
This Priceline deal was found by Cheapflights users on 10/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/143:26 pmPDX - ORD
1 stop6h 49mFrontier
Sun 11/166:00 amORD - PDX
1 stop7h 56mFrontier
Deal found 10/28$234
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Sat 12/139:48 amPDX - ORD
1 stop12h 25mFrontier
Sun 12/145:13 pmORD - PDX
2 stops17h 23mFrontier
Deal found 10/28$235
This Alaska Airlines deal was found by Cheapflights users on 10/28. 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 11/181:38 pmPDX - ORD
1 stop8h 46mAlaska Airlines
Wed 11/198:00 amORD - PDX
1 stop6h 38mAlaska Airlines
Deal found 10/28$236

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 October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$131
(Frontier)

One-way from

$63
(Trip.com)

Popular in

March

Cheapest in

August

Average price

$339

Good round-trip deal

$334 or less

Good one-way deal

$177 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. 9% potential increase in price ($34 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 October 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 October 29, 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

Sun 12/7

11:59 pm-5:52 am

Nonstop3h 53m

Chicago O'Hare Intl

Tue 12/9

4:10 pm-6:45 pm

Nonstop4h 35m

$227

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 12/10

11:59 pm-5:52 am

Nonstop3h 53m

Chicago O'Hare Intl

Mon 12/15

7:37 pm-10:15 pm

Nonstop4h 38m

$227

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 12/10

7:04 am-1:09 pm

Nonstop4h 05m

Chicago O'Hare Intl

Mon 12/15

8:00 am-1:50 pm

1 stop7h 50m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

Mon 12/8

12:32 am-8:40 am

1 stop6h 08m

Chicago O'Hare Intl

Tue 12/16

7:20 am-12:40 pm

1 stop7h 20m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 12/9

12:32 am-8:40 am

1 stop6h 08m

Chicago O'Hare Intl

Tue 12/16

6:00 am-12:54 pm

1 stop8h 54m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 12/12

12:32 am-10:33 am

1 stop8h 01m

Chicago O'Hare Intl

Tue 12/16

7:20 am-12:40 pm

1 stop7h 20m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 1/16

11:59 pm-6:00 am

Nonstop4h 01m

Chicago O'Hare Intl

Tue 1/20

8:45 am-1:45 pm

1 stop7h 00m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 2/27

8:40 am-5:50 pm

1 stop7h 10m

Chicago O'Hare Intl

Mon 3/2

2:05 pm-4:39 pm

Nonstop4h 34m

$247

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 3/10

7:00 am-1:04 pm

Nonstop4h 04m

Chicago O'Hare Intl

Wed 3/11

2:05 pm-4:39 pm

Nonstop4h 34m

$247

PortlandChicago

PDX - ORD

PDXORD

Portland

Sun 1/11

1:30 pm-11:53 pm

1 stop8h 23m

Chicago O'Hare Intl

Wed 1/14

7:30 am-12:44 pm

1 stop7h 14m

$247

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

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 $256). 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 October 29, 2025.

It’s optimal to fly from Oregon to Illinois in the afternoon. By choosing this option you can save up to 29% on the cost of your flight, compared to a flight in the morning.

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 November 10, 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.

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

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 October 29, 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
11,210 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.0

Crew

8.5

Food

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Alaska Airlines
8.0
Very good
11,210 reviews
Alaska Airlines
8.0
Very good
11,210 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.0

Crew

8.5

Food

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Southwest
8.0
Very good
4,241 reviews
Alaska Airlines
8.0
Very good
11,210 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.0

Crew

8.5

Food

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Delta
7.9
Good
7,992 reviews
Alaska Airlines
8.0
Very good
11,210 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.0

Crew

8.5

Food

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
United Airlines
7.4
Good
8,999 reviews
Alaska Airlines
8.0
Very good
11,210 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.0

Crew

8.5

Food

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
American Airlines
7.2
Good
11,032 reviews
Alaska Airlines
8.0
Very good
11,210 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.0

Crew

8.5

Food

7.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

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 3h 53m. United Airlines provides one of the quickest options available for as low as $227. 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 $109. Users have also found prices from $114 and $114 on Alaska Airlines and United 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 $256). 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

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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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$94Average$280FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$119Average$194FlexibilityNo cancel feeOn-time65%
DeltaCheapest$123Average$361FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$125Average$324FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$194Average$464FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$197Average$383FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$224Average$472FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$246Average$427FlexibilityNo cancel feeOn-time63%

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