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$79+ 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 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PDX
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Illinois to Portland

Keep the following information in mind while searching for Illinois to Portland flight deals. Data was last updated September 17, 2025.

Round-trip from

$202
(Vliegwinkel)

One-way from

$79
(Priceline)

Popular in

December

Cheapest in

January

Average price

$278

Good round-trip deal

$249 or less

Good one-way deal

$89 or less
From Illinois to Portland
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One-way flight from Illinois to Portland
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Highest demand for flights based on searches. 2% potential increase in price ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Illinois to Portland.
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Price to beat on a one-way flight from Illinois to Portland.
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Find 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 September 17, 2025.

This Vliegwinkel deal was found by Cheapflights users on 9/15. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/252:04 pmORD - PDX
Nonstop4h 33mHawaiian Airlines
Fri 10/3111:00 pmPDX - ORD
Nonstop4h 01mHawaiian Airlines
Deal found 9/15$202
This Frontier deal was found by Cheapflights users on 9/16. 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 11/79:47 pmORD - PDX
2 stops16h 09mFrontier
Mon 11/103:26 pmPDX - ORD
1 stop6h 49mFrontier
Deal found 9/16$203
This Booking.com deal was found by Cheapflights users on 9/15. 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 10/106:24 pmMDW - PDX
1 stop19h 24mFrontier
Sun 10/1212:43 pmPDX - MDW
1 stop9h 53mFrontier
Deal found 9/15$204
This Booking.com deal was found by Cheapflights users on 9/15. 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.
Sun 9/286:00 amORD - PDX
1 stop20h 12mFrontier
Wed 10/17:15 amPDX - ORD
1 stop12h 13mFrontier
Deal found 9/15$204
This Southwest deal was found by Cheapflights users on 9/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/128:45 amMDW - PDX
1 stop8h 35mSouthwest
Sun 11/165:30 amPDX - MDW
2 stops12h 15mSouthwest
Deal found 9/16$205
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Thu 10/167:09 amORD - PDX
Nonstop4h 22mAmerican Airlines
Tue 10/2111:58 pmPDX - ORD
Nonstop3h 55mAmerican Airlines
Deal found 9/17$205
This Expedia deal was found by Cheapflights users on 9/16. 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.
Wed 10/157:15 amORD - PDX
1 stop6h 33mMultiple Airlines
Wed 11/1911:00 pmPDX - ORD
Nonstop4h 01mMultiple Airlines
Deal found 9/16$207
This Southwest deal was found by Cheapflights users on 9/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:25 pmMDW - PDX
2 stops7h 50mSouthwest
Sun 11/165:30 amPDX - MDW
2 stops12h 15mSouthwest
Deal found 9/16$210
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 11/66:00 amORD - PDX
1 stop7h 56mMultiple Airlines
Tue 11/117:00 amPDX - ORD
Nonstop4h 09mMultiple Airlines
Deal found 9/15$210
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/187:00 amORD - PDX
Nonstop4h 32mMultiple Airlines
Tue 10/2112:43 pmPDX - ORD
1 stop9h 10mMultiple Airlines
Deal found 9/15$211
This Orbitz deal was found by Cheapflights users on 9/15. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/292:05 pmORD - PDX
Nonstop4h 36mMultiple Airlines
Tue 11/412:52 pmPDX - ORD
1 stop9h 20mMultiple Airlines
Deal found 9/15$212
This Southwest deal was found by Cheapflights users on 9/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/139:50 pmMDW - PDX
Nonstop4h 30mSouthwest
Sat 11/227:40 pmPDX - MDW
1 stop7h 25mSouthwest
Deal found 9/16$213

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 September 17, 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

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Thu 11/13

9:50 pm-12:20 am

Nonstop4h 30m

Portland

Sat 11/22

7:40 pm-5:05 am

1 stop7h 25m

$213

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 10/21

1:48 pm-8:26 pm

1 stop8h 38m

Portland

Wed 10/29

6:00 am-4:09 pm

1 stop8h 09m

$231

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 10/14

1:10 pm-3:30 pm

Nonstop4h 20m

Portland

Tue 10/21

2:15 pm-8:25 pm

Nonstop4h 10m

$231

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Tue 10/21

6:05 pm-10:40 pm

1 stop6h 35m

Portland

Wed 10/29

7:30 am-6:41 pm

2 stops9h 11m

$234

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 10/21

8:25 pm-10:50 pm

Nonstop4h 25m

Portland

Wed 10/29

5:10 am-2:05 pm

1 stop6h 55m

$241

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 10/8

5:01 am-9:29 am

1 stop6h 28m

Portland

Sat 10/11

2:15 pm-8:25 pm

Nonstop4h 10m

$241

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 10/29

9:05 am-11:48 am

Nonstop4h 43m

Portland

Sat 11/1

7:38 pm-6:02 am

1 stop8h 24m

$241

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Mon 11/24

2:12 pm-7:19 pm

1 stop7h 07m

Portland

Fri 11/28

5:30 am-1:44 pm

1 stop6h 14m

$242

St. LouisPortland

STL - PDX

STLPDX

Lambert-St Louis

Tue 10/7

6:33 am-12:25 pm

1 stop7h 52m

Portland

Tue 10/7

4:25 pm-12:03 am

1 stop5h 38m

$243

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Mon 10/27

7:00 am-9:39 am

Nonstop4h 39m

Portland

Tue 11/18

7:00 am-1:09 pm

Nonstop4h 09m

$244

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

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, November is the cheapest month in which you can book a flight from Illinois to Portland (average of $277). Flying from Illinois to Portland in March is currently the most expensive (average of $368). 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 September 17, 2025.

When flying from Illinois to Portland, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 September 17, 2025.

The most flights from USIL to PDX are scheduled on a Monday (27 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (14 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 20m. Southwest provides one of the quickest options available for as low as $231. 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 Southwest, which is currently one of the cheapest options available, starting at $103. Delta flights start at $104 while deals on Alaska Airlines start at $116 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, Chicago Midway - Portland or Lambert-St Louis - 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: United Airlines (79%), Alaska Airlines (78%), Hawaiian Airlines( 78%).

  • What are the cheapest flights from Illinois to Portland?

    Looking for the cheapest flight from Illinois to Portland? While on average our users pay $773, our data indicates the cheapest price to be $103. The most popular route (Chicago O'Hare Intl - Portland), is priced around $175.

  • 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, November is the cheapest month in which you can book a flight from Illinois to Portland (average of $277). Flying from Illinois to Portland in March is currently the most expensive (average of $368). 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
Beaverton
Clackamas
McMinnville
Lake Oswego
Hillsboro
Cannon Beach
Long Beach
Longview
Lincoln City
Tigard
Depoe Bay
Stevenson
Wilsonville
Pacific City
Tillamook
Troutdale
Gresham
Silverton

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Illinois to Portland

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Top 8 airlines flying from Illinois to Portland

Discover the top 8 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$86Average$184FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$179FlexibilityNo cancel feeOn-time62%
DeltaCheapest$123Average$328FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$134Average$284FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$183Average$289FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$213Average$456FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$227Average$431FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$238Average$453FlexibilityNo cancel feeOn-time63%

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