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$120+ 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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PDX
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
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 July 27, 2026.

This American Airlines deal was found by Cheapflights users on 7/22. 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.
Sat 9/126:00 am
MLI
-
PDX
1 stop6h 55m
American Airlines
Sat 9/197:00 am
PDX
-
MLI
1 stop7h 03m
American Airlines
Deal found 7/22$291
This Alaska Airlines deal was found by Cheapflights users on 7/22. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:08 pm
STL
-
PDX
Nonstop4h 12m
Alaska Airlines
Sat 9/1911:16 am
PDX
-
STL
Nonstop3h 54m
Alaska Airlines
Deal found 7/22$297
This CheapOair deal was found by Cheapflights users on 7/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/97:10 pm
STL
-
PDX
1 stop23h 44m
Frontier
Mon 8/175:49 pm
PDX
-
STL
1 stop22h 01m
Frontier
Deal found 7/22$298
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/247:58 pm
STL
-
PDX
1 stop23h 13m
Frontier
Sun 8/3012:20 pm
PDX
-
STL
1 stop28h 53m
Frontier
Deal found 7/26$300
This Frontier deal was found by Cheapflights users on 7/23. 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.
Mon 8/107:29 am
ORD
-
PDX
1 stop11h 25m
Frontier
Fri 8/145:49 pm
PDX
-
ORD
1 stop9h 48m
Frontier
Deal found 7/23$301
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 8/129:57 pm
ORD
-
PDX
1 stop20h 54m
Frontier
Fri 8/145:49 pm
PDX
-
ORD
1 stop9h 48m
Frontier
Deal found 7/23$302
This Priceline deal was found by Cheapflights users on 7/23. 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.
Sat 8/157:20 am
ORD
-
PDX
Nonstop4h 25m
Multiple Airlines
Sat 8/295:56 pm
PDX
-
ORD
1 stop10h 03m
Multiple Airlines
Deal found 7/23$303
This CheapOair deal was found by Cheapflights users on 7/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/192:41 pm
ORD
-
PDX
1 stop28h 30m
Frontier
Sat 8/225:56 pm
PDX
-
ORD
1 stop10h 03m
Frontier
Deal found 7/22$304
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:58 pm
STL
-
PDX
1 stop23h 13m
Frontier
Thu 9/312:20 pm
PDX
-
STL
2 stops27h 02m
Frontier
Deal found 7/26$304
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Fri 8/149:57 pm
ORD
-
PDX
1 stop20h 54m
Frontier
Tue 9/15:56 pm
PDX
-
ORD
1 stop17h 40m
Frontier
Deal found 7/22$305
This Kiwi.com deal was found by Cheapflights users on 7/24. 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 9/102:46 pm
ORD
-
PDX
2 stops22h 57m
Frontier
Sun 9/1312:38 pm
PDX
-
ORD
1 stop20h 43m
Frontier
Deal found 7/24$306
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/287:58 pm
STL
-
PDX
1 stop23h 13m
Frontier
Sat 9/512:20 pm
PDX
-
STL
1 stop28h 53m
Frontier
Deal found 7/26$306

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 July 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$291
(American Airlines)

One-way from

$120
(Frontier)

Popular in

March

Cheapest in

January

Average price

$382

Good round-trip deal

$325 or less

Good one-way deal

$200 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
High demand for flights, 2% potential price rise
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 July 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 July 27, 2026.
Use the filters below to find and compare flights from Illinois to Portland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

St. LouisPortland

STL - PDX

STLPDX

Lambert-St Louis

Sat 9/12

6:08 pm-8:20 pm

Nonstop4h 12m

Portland

Sat 9/19

11:16 am-5:10 pm

Nonstop3h 54m

$297

MolinePortland

MLI - PDX

MLIPDX

Moline Quad-City

Wed 9/9

5:08 pm-10:52 pm

1 stop7h 44m

Portland

Tue 9/15

8:05 am-5:26 pm

1 stop7h 21m

$301

MolinePortland

MLI - PDX

MLIPDX

Moline Quad-City

Fri 9/11

2:08 pm-7:18 pm

1 stop7h 10m

Portland

Tue 9/15

11:02 pm-10:07 am

1 stop9h 05m

$301

St. LouisPortland

STL - PDX

STLPDX

Lambert-St Louis

Fri 10/23

5:05 am-9:50 am

1 stop6h 45m

Portland

Tue 10/27

1:10 pm-10:05 pm

1 stop6h 55m

$318

St. LouisPortland

STL - PDX

STLPDX

Lambert-St Louis

Thu 10/22

5:05 am-9:50 am

1 stop6h 45m

Portland

Sun 10/25

11:35 pm-9:00 am

1 stop7h 25m

$324

St. LouisPortland

STL - PDX

STLPDX

Lambert-St Louis

Thu 9/3

7:45 pm-11:39 pm

1 stop5h 54m

Portland

Sun 9/6

5:45 am-1:38 pm

1 stop5h 53m

$329

St. LouisPortland

STL - PDX

STLPDX

Lambert-St Louis

Mon 8/17

11:50 am-7:20 pm

2 stops9h 30m

Portland

Sat 8/22

10:45 pm-9:20 am

1 stop8h 35m

$334

St. LouisPortland

STL - PDX

STLPDX

Lambert-St Louis

Sun 11/1

7:15 pm-11:55 pm

1 stop6h 40m

Portland

Mon 11/9

8:00 am-7:10 pm

2 stops9h 10m

$334

St. LouisPortland

STL - PDX

STLPDX

Lambert-St Louis

Sun 8/16

6:15 am-11:20 am

1 stop7h 05m

Portland

Fri 8/21

10:45 pm-1:25 pm

2 stops12h 40m

$340

St. LouisPortland

STL - PDX

STLPDX

Lambert-St Louis

Sat 8/22

6:08 pm-8:20 pm

Nonstop4h 12m

Portland

Sat 8/29

11:16 am-5:10 pm

Nonstop3h 54m

$342

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/24

Showing 1-10 of 60 resultsSorted by cheapest first
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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, February is the cheapest month in which you can book a flight from Illinois to Portland (average of $294). Flying from Illinois to Portland in March is currently the most expensive (average of $399). 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 July 27, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 34% on flights from Illinois to Portland by exploring options for tickets in the evening.

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 July 27, 2026.

The most flights from USIL to PDX are scheduled on a Saturday (28 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (24 on average).

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

Airfare is typical for this route at the moment.
Illinois to Portland flights typically cost between $271 and $448 in August.
The cheapest round-trip price found within the last 5 days was $301 on Frontier (Aug 10-Aug 14).

How far ahead should I book a flight from Illinois to Portland?

To ensure you get the cheapest price possible for a flight from Illinois to Portland, you should look to book at least 63 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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 July 25, 2026.

Travelers seeking maximum savings on their Illinois to Portland flight should consider departing on Saturday afternoons 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.

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 12m. Alaska Airlines provides one of the quickest options available for as low as $297. There are 1702 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 $89. Frontier flights start at $98 while deals on American Airlines start at $98 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: Alaska Airlines (80%), Air Canada (74%), United Airlines( 69%).

  • What are the cheapest flights from Illinois to Portland?

    Looking for the cheapest flight from Illinois to Portland? While on average our users pay $710, our data indicates the cheapest price to be $158. The most popular route (Chicago O'Hare Intl - Portland), is priced around $267.

  • 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, February is the cheapest month in which you can book a flight from Illinois to Portland (average of $294). Flying from Illinois to Portland in March is currently the most expensive (average of $399). 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
Beaverton
Seaside
Lincoln City
Vancouver
Longview
Lake Oswego
Hillsboro
Kelso
Clackamas
Troutdale
Cannon Beach
Long Beach
McMinnville
The Dalles
Wilsonville
Depoe Bay
Stevenson
Tillamook
Astoria
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 6 airlines flying from Illinois to Portland

Discover the top 6 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 July 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$150Average$317FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$191Average$218FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$197Average$329FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$207Average$467FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$212Average$422FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$227Average$372FlexibilityNo cancel feeOn-time63%

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