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$102+ Cheap flights from Illinois to Portland (PDX)

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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PDX
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
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Cheap flight deals from Illinois to Portland

Cheapest flights from Illinois to Portland
Explore the most affordable flight options available from Illinois to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 28, 2025.

This American Airlines deal was found by Cheapflights users on 12/25. 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 12/263:30 pmSTL - PDX
1 stop9h 36mAmerican Airlines
Thu 1/13:02 pmPDX - STL
1 stop6h 42mAmerican Airlines
Deal found 12/25$421
This Expedia deal was found by Cheapflights users on 12/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/307:00 amORD - PDX
1 stop6h 43mFrontier
Thu 1/112:47 pmPDX - ORD
1 stop9h 25mFrontier
Deal found 12/26$512
This Expedia deal was found by Cheapflights users on 12/25. 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.
Tue 12/307:00 amORD - PDX
1 stop6h 43mMultiple Airlines
Sat 1/311:00 pmPDX - ORD
Nonstop4h 02mMultiple Airlines
Deal found 12/25$525
This Frontier deal was found by Cheapflights users on 12/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/287:00 amORD - PDX
1 stop6h 43mFrontier
Tue 12/3012:47 pmPDX - ORD
1 stop9h 25mFrontier
Deal found 12/26$532
This American Airlines deal was found by Cheapflights users on 12/27. 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.
Tue 12/303:30 pmBMI - PDX
1 stop9h 36mAmerican Airlines
Mon 1/53:02 pmPDX - BMI
1 stop6h 40mAmerican Airlines
Deal found 12/27$536
This American Airlines deal was found by Cheapflights users on 12/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/266:52 pmORD - PDX
1 stop8h 02mAmerican Airlines
Sat 1/106:00 amPDX - ORD
Nonstop4h 15mAmerican Airlines
Deal found 12/26$547
This Delta deal was found by Cheapflights users on 12/25. 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.
Mon 12/292:18 pmSTL - PDX
1 stop5h 56mDelta
Sat 1/31:45 pmPDX - STL
1 stop5h 49mDelta
Deal found 12/25$548
This Delta deal was found by Cheapflights users on 12/25. 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 12/316:00 amORD - PDX
1 stop7h 38mDelta
Sun 1/115:30 amPDX - ORD
1 stop5h 52mDelta
Deal found 12/25$557
This United Airlines deal was found by Cheapflights users on 12/27. 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.
Wed 12/318:35 amPIA - PDX
2 stops12h 13mUnited Airlines
Fri 1/211:02 amPDX - PIA
1 stop8h 37mUnited Airlines
Deal found 12/27$558
This American Airlines deal was found by Cheapflights users on 12/27. 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.
Mon 12/298:00 amSTL - PDX
1 stop7h 49mAmerican Airlines
Wed 1/76:00 amPDX - STL
1 stop8h 14mAmerican Airlines
Deal found 12/27$567
This Kiwi.com deal was found by Cheapflights users on 12/25. 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 12/317:44 pmORD - PDX
1 stop17h 53mMultiple Airlines
Sat 1/105:26 pmPDX - ORD
2 stops15h 56mMultiple Airlines
Deal found 12/25$568
This United Airlines deal was found by Cheapflights users on 12/27. 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.
Tue 12/301:20 pmPIA - PDX
1 stop7h 41mUnited Airlines
Mon 1/511:55 pmPDX - PIA
1 stop8h 15mUnited Airlines
Deal found 12/27$574

Find flight deals from Illinois to Portland

Keep the following information in mind while searching for Illinois to Portland flight deals. Data was last updated December 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$203
(Expedia)

One-way from

$102
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$427

Good round-trip deal

$261 or less

Good one-way deal

$215 or less
Provider with most accurate pricing for Chicago (CHI)-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Portland flights.
Search Deals
From Illinois to Portland
Search Deals
One-way flight from Illinois to Portland
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 ($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 Illinois to Portland.
Search Deals
Price to beat on a one-way flight from Illinois to Portland.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois to Portland 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 28, 2025.
Use the filters below to find and compare flights from Illinois to Portland that are best for you.

Fly from

Illinois

Fly to

Portland

Route

Depart

Return

Price

St. LouisPortland

STL - PDX

STLPDX

Lambert-St Louis

Wed 3/11

8:12 pm-11:09 am

1 stop16h 57m

Portland

Mon 3/16

9:53 am-12:15 pm

2 stops24h 22m

$227

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Mon 3/2

2:07 pm-4:50 pm

Nonstop4h 43m

Portland

Wed 3/4

7:00 am-1:11 pm

Nonstop4h 11m

$227

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 2/5

9:10 am-11:57 am

Nonstop4h 47m

Portland

Wed 2/11

7:00 am-1:05 pm

Nonstop4h 05m

$227

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Fri 3/13

2:07 pm-4:50 pm

Nonstop4h 43m

Portland

Tue 3/17

7:00 am-1:11 pm

Nonstop4h 11m

$227

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 2/19

9:10 am-11:55 am

Nonstop4h 45m

Portland

Wed 2/25

10:56 am-4:54 pm

Nonstop3h 58m

$227

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Mon 3/9

2:07 pm-4:50 pm

Nonstop4h 43m

Portland

Wed 3/11

7:00 am-1:11 pm

Nonstop4h 11m

$227

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 2/25

6:25 am-12:38 pm

1 stop8h 13m

Portland

Wed 2/25

11:59 pm-5:53 am

Nonstop3h 54m

$227

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 3/5

2:07 pm-4:50 pm

Nonstop4h 43m

Portland

Sat 3/7

7:00 am-1:11 pm

Nonstop4h 11m

$227

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 2/24

2:07 pm-4:50 pm

Nonstop4h 43m

Portland

Thu 2/26

7:00 am-1:11 pm

Nonstop4h 11m

$227

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Sat 3/21

10:30 pm-12:55 am

Nonstop4h 25m

Portland

Fri 3/27

11:55 pm-5:45 am

Nonstop3h 50m

$232

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/27

Showing 1-10 of 60 results
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Best time to book a flight from Illinois to Portland

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

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

Currently, January is the cheapest month in which you can book a flight from Illinois to Portland (average of $123). Flying from Illinois to Portland in December is currently the most expensive (average of $207). 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 IL to PDX?

Find hourly flight availability from Illinois to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 28, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 35% on flights from Illinois to Portland by exploring options for tickets in the evening.

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

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

Travelers seeking maximum savings on their Illinois to Portland flight should consider departing on Thursday evenings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Illinois to Portland

Explore weekly flight availability from Illinois to Portland. 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 December 28, 2025.

The most flights from USIL to PDX are scheduled on a Friday (17 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (9 on average).

Related info for your journey

Find useful and relevant information for your journey from Illinois to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Portland from Illinois?

    For a flight from Illinois to Portland, you will be flying into Portland. Portland (PDX) is just 6.0 mi from the center of the city.

  • How long is the flight from Illinois to Portland?

    A quick flight from Illinois to Portland can take about 4h 43m. Frontier provides one of the quickest options available for as low as $227. There are 1733 mi between Illinois and Portland. Both multi-stop and nonstop flights can be found to your destination and back.

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $55. Spirit Airlines flights start at $70 while deals on Hawaiian Airlines start at $73 one-way.

  • What are the most popular routes from Illinois to Portland?

    When deciding which route to take from Illinois to Portland consider Chicago O'Hare Intl - Portland, Lambert-St Louis - Portland or Chicago Midway - Portland as they are the most popular.

  • What are the most reliable airlines from Illinois to Portland?

    Before booking your flight to Portland from Illinois, check out the most reliable airlines to get you to your destination on time: Air Canada (66%), United Airlines (65%), Alaska Airlines( 62%).

  • What are the cheapest flights from Illinois to Portland?

    Looking for the cheapest flight from Illinois to Portland? While on average our users pay $560, our data indicates the cheapest price to be $118. The most popular route (Chicago O'Hare Intl - Portland), is priced around $217.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Illinois to Portland (average of $123). Flying from Illinois to Portland in December is currently the most expensive (average of $207). 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 Portland?

Book flights to Portland if you plan to visit one of these locations
Vancouver
Seaside
Clackamas
Lincoln City
Longview
Lake Oswego
Beaverton
McMinnville
Hillsboro
Troutdale
Cannon Beach
Long Beach
Tigard
The Dalles
Depoe Bay
Stevenson
Wilsonville
Tillamook
Pacific City
Gresham

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Alternative routes for Illinois to Portland

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Top 7 airlines flying from Illinois to Portland

Discover the top 7 airlines that operate flights from Illinois to Portland. 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 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$93Average$182FlexibilityNo cancel feeOn-time65%
Hawaiian AirlinesCheapest$134Average$284FlexibilityNo cancel feeOn-time85%
FrontierCheapest$138Average$220FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$199Average$309FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$211Average$408FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$213Average$454FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$238Average$441FlexibilityNo cancel feeOn-time63%

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