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$85+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PDX
Feb 22 — Mar 11
Sun 2/22
Sun 3/1
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 January 23, 2026.

This Southwest deal was found by Cheapflights users on 1/22. 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.
Sat 2/148:30 pm
MDW
-
PDX
Nonstop4h 30m
Southwest
Mon 2/236:45 am
PDX
-
MDW
Nonstop3h 55m
Southwest
Deal found 1/22$207
This American Airlines deal was found by Cheapflights users on 1/22. 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 2/128:25 am
ORD
-
PDX
Nonstop4h 33m
American Airlines
Tue 2/1711:35 pm
PDX
-
ORD
Nonstop3h 57m
American Airlines
Deal found 1/22$207
This American Airlines deal was found by Cheapflights users on 1/21. 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 2/411:20 am
ORD
-
PDX
Nonstop4h 33m
American Airlines
Wed 2/112:43 pm
PDX
-
ORD
Nonstop4h 19m
American Airlines
Deal found 1/21$214
This Delta deal was found by Cheapflights users on 1/22. 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 2/251:49 pm
MDW
-
PDX
1 stop8h 41m
Delta
Tue 3/312:09 pm
PDX
-
MDW
1 stop8h 24m
Delta
Deal found 1/22$217
This United Airlines deal was found by Cheapflights users on 1/20. 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.
Sat 2/144:00 pm
ORD
-
PDX
1 stop8h 59m
United Airlines
Wed 2/1811:59 pm
PDX
-
ORD
Nonstop3h 54m
United Airlines
Deal found 1/20$217
This American Airlines deal was found by Cheapflights users on 1/21. 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 2/139:46 pm
ORD
-
PDX
Nonstop4h 31m
American Airlines
Sun 2/2211:35 pm
PDX
-
ORD
Nonstop3h 57m
American Airlines
Deal found 1/21$218
This eDestinos deal was found by Cheapflights users on 1/22. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/810:53 am
ORD
-
PDX
1 stop26h 16m
Multiple Airlines
Sun 3/157:00 am
PDX
-
ORD
Nonstop4h 11m
Multiple Airlines
Deal found 1/22$222
This Southwest deal was found by Cheapflights users on 1/20. 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 4/293:40 pm
MDW
-
PDX
1 stop7h 05m
Southwest
Fri 5/111:55 pm
PDX
-
MDW
Nonstop3h 55m
Southwest
Deal found 1/20$223
This American Airlines deal was found by Cheapflights users on 1/22. 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 2/139:46 pm
ORD
-
PDX
Nonstop4h 31m
American Airlines
Sun 2/1511:35 pm
PDX
-
ORD
Nonstop3h 57m
American Airlines
Deal found 1/22$223
This Alaska Airlines deal was found by Cheapflights users on 1/20. 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 2/36:06 pm
ORD
-
PDX
1 stop6h 40m
Alaska Airlines
Tue 2/107:05 am
PDX
-
ORD
Nonstop4h 05m
Alaska Airlines
Deal found 1/20$224
This Kiwi.com deal was found by Cheapflights users on 1/22. 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 2/142:07 pm
ORD
-
PDX
Nonstop4h 43m
Hawaiian Airlines
Sat 2/218:30 am
PDX
-
ORD
1 stop6h 03m
Hawaiian Airlines
Deal found 1/22$225
This Delta deal was found by Cheapflights users on 1/20. 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 3/112:05 pm
MDW
-
PDX
1 stop8h 20m
Delta
Wed 3/1112:30 am
PDX
-
MDW
1 stop6h 20m
Delta
Deal found 1/20$227

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 January 23, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$207
(American Airlines)

One-way from

$85
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$307

Good round-trip deal

$237 or less

Good one-way deal

$138 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. 6% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 23, 2026.
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

Wed 2/18

1:55 pm-10:35 pm

1 stop10h 40m

Portland

Wed 2/25

6:30 am-12:25 pm

Nonstop3h 55m

$217

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 2/25

1:49 pm-8:30 pm

1 stop8h 41m

Portland

Mon 3/2

12:40 am-9:06 am

1 stop6h 26m

$217

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 2/21

9:10 am-11:55 am

Nonstop4h 45m

Portland

Thu 2/26

12:57 pm-11:04 pm

1 stop8h 07m

$217

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 2/17

8:10 am-10:45 am

Nonstop4h 35m

Portland

Tue 2/24

6:30 am-12:25 pm

Nonstop3h 55m

$217

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Wed 2/18

1:49 pm-8:30 pm

1 stop8h 41m

Portland

Tue 2/24

12:40 am-9:06 am

1 stop6h 26m

$217

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 2/26

7:59 pm-10:40 pm

Nonstop4h 41m

Portland

Sun 3/1

11:59 pm-5:53 am

Nonstop3h 54m

$217

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Thu 2/19

8:10 am-10:45 am

Nonstop4h 35m

Portland

Mon 2/23

6:45 am-12:40 pm

Nonstop3h 55m

$217

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 2/28

6:15 am-12:44 pm

1 stop8h 29m

Portland

Sat 2/28

9:45 pm-8:38 am

1 stop8h 53m

$217

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 2/24

1:49 pm-8:30 pm

1 stop8h 41m

Portland

Thu 2/26

12:40 am-9:06 am

1 stop6h 26m

$227

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 2/27

5:20 pm-12:05 am

1 stop8h 45m

Portland

Wed 4/1

5:25 am-11:20 am

Nonstop3h 55m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

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 $124). 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 January 23, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 25% 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 January 17, 2026.

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 January 23, 2026.

The most flights from USIL to PDX are scheduled on a Thursday (17 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 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 45m. Southwest provides one of the quickest options available for as low as $217. 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, 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: Malaysia Airlines (80%), British Airways (75%), Air Canada( 74%).

  • What are the cheapest flights from Illinois to Portland?

    Looking for the cheapest flight from Illinois to Portland? While on average our users pay $521, our data indicates the cheapest price to be $108. The most popular route (Chicago O'Hare Intl - Portland), is priced around $197.

  • 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 $124). 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
Hillsboro
Troutdale
Cannon Beach
Long Beach
McMinnville
Tigard
The Dalles
Depoe Bay
Stevenson
Wilsonville
Tillamook
Pacific City
Gresham

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Illinois to Portland

See prices for flight routes from nearby airports that may be better suited for you.
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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 January 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$86Average$179FlexibilityNo cancel feeOn-time65%
Hawaiian AirlinesCheapest$128Average$272FlexibilityNo cancel feeOn-time85%
FrontierCheapest$150Average$227FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$197Average$309FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$205Average$405FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$211Average$449FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$247Average$419FlexibilityNo cancel feeOn-time63%

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