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$128+ 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 6/12. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PDX
Jun 19 — Jun 261
Fri 6/19
Fri 6/26
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 May 20, 2026.

This American Airlines deal was found by Cheapflights users on 5/19. 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 9/126:38 pm
MLI
-
PDX
1 stop6h 12m
American Airlines
Sat 9/196:35 am
PDX
-
MLI
1 stop7h 26m
American Airlines
Deal found 5/19$291
This Alaska Airlines deal was found by Cheapflights users on 5/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/85:59 pm
STL
-
PDX
Nonstop4h 10m
Alaska Airlines
Tue 9/1511:15 am
PDX
-
STL
Nonstop3h 48m
Alaska Airlines
Deal found 5/15$299
This Southwest deal was found by Cheapflights users on 5/18. 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 5/278:50 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Fri 5/295:10 am
PDX
-
MDW
Nonstop3h 55m
Southwest
Deal found 5/18$305
This United Airlines deal was found by Cheapflights users on 5/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/248:57 am
ORD
-
PDX
Nonstop4h 41m
United Airlines
Wed 5/2711:40 pm
PDX
-
ORD
Nonstop4h 05m
United Airlines
Deal found 5/17$305
This Southwest deal was found by Cheapflights users on 5/16. 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.
Fri 5/294:35 pm
MDW
-
PDX
2 stops10h 20m
Southwest
Sat 6/611:30 pm
PDX
-
MDW
Nonstop3h 50m
Southwest
Deal found 5/16$306
This Travelocity deal was found by Cheapflights users on 5/18. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/87:20 am
ORD
-
PDX
Nonstop4h 25m
Multiple Airlines
Mon 8/106:59 pm
PDX
-
ORD
1 stop8h 29m
Multiple Airlines
Deal found 5/18$307
This Frontier deal was found by Cheapflights users on 5/18. 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 7/237:15 am
ORD
-
PDX
1 stop12h 49m
Frontier
Mon 7/276:59 pm
PDX
-
ORD
1 stop8h 29m
Frontier
Deal found 5/18$308
This Southwest deal was found by Cheapflights users on 5/16. 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.
Sat 8/228:30 am
STL
-
PDX
Nonstop4h 10m
Southwest
Sun 8/3011:30 pm
PDX
-
STL
1 stop9h 00m
Southwest
Deal found 5/16$309
This Travelocity deal was found by Cheapflights users on 5/18. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/27:20 am
ORD
-
PDX
1 stop12h 04m
Frontier
Sun 7/56:59 pm
PDX
-
ORD
1 stop8h 29m
Frontier
Deal found 5/18$309
This Southwest deal was found by Cheapflights users on 5/18. 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 7/46:05 pm
MDW
-
PDX
Nonstop4h 20m
Southwest
Tue 7/711:30 pm
PDX
-
MDW
Nonstop3h 50m
Southwest
Deal found 5/18$310
This American Airlines deal was found by Cheapflights users on 5/19. 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 7/37:20 pm
ORD
-
PDX
Nonstop4h 30m
American Airlines
Sat 7/1111:15 pm
PDX
-
ORD
Nonstop3h 59m
American Airlines
Deal found 5/19$310
This Booking.com deal was found by Cheapflights users on 5/15. 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.
Thu 8/208:08 pm
STL
-
PDX
1 stop22h 49m
Frontier
Mon 8/246:19 pm
PDX
-
STL
1 stop21h 49m
Frontier
Deal found 5/15$311

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 May 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$291
(American Airlines)

One-way from

$128
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$325

Good round-trip deal

$305 or less

Good one-way deal

$163 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. 3% potential increase in price ($10 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 20, 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

St. LouisPortland

STL - PDX

STLPDX

Lambert-St Louis

Fri 7/3

5:36 pm-11:18 pm

1 stop7h 42m

Portland

Thu 7/9

11:15 pm-9:31 am

1 stop8h 16m

$319

St. LouisPortland

STL - PDX

STLPDX

Lambert-St Louis

Tue 6/30

6:20 pm-12:05 am

1 stop7h 45m

Portland

Sat 7/11

4:25 pm-12:35 am

1 stop6h 10m

$319
Quickest round-trip

St. LouisPortland

STL - PDX

STLPDX

Lambert-St Louis

Tue 7/21

5:37 pm-7:47 pm

Nonstop4h 10m

Portland

Tue 8/25

11:16 am-5:10 pm

Nonstop3h 54m

$319

St. LouisPortland

STL - PDX

STLPDX

Lambert-St Louis

Fri 7/3

11:18 am-5:37 pm

1 stop8h 19m

Portland

Thu 7/9

12:33 am-10:28 am

1 stop7h 55m

$319

St. LouisPortland

STL - PDX

STLPDX

Lambert-St Louis

Mon 8/3

6:30 pm-11:55 pm

1 stop7h 25m

Portland

Thu 8/6

11:30 pm-10:30 am

1 stop9h 00m

$319

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 7/17

9:35 pm-11:55 pm

Nonstop4h 20m

Portland

Tue 7/21

11:30 pm-5:20 am

Nonstop3h 50m

$326

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Tue 6/16

9:10 pm-11:30 pm

Nonstop4h 20m

Portland

Thu 6/25

11:30 pm-5:20 am

Nonstop3h 50m

$326

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Sat 6/20

6:30 am-12:40 pm

1 stop8h 10m

Portland

Fri 6/26

12:33 am-8:35 am

1 stop6h 02m

$335

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 7/23

7:00 am-9:34 am

Nonstop4h 34m

Portland

Mon 7/27

11:40 pm-5:45 am

Nonstop4h 05m

$337

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

Fri 7/3

4:40 pm-7:00 pm

Nonstop4h 20m

Portland

Sun 7/5

11:30 pm-5:20 am

Nonstop3h 50m

$341

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/19

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, October is the cheapest month in which you can book a flight from Illinois to Portland (average of $99). Flying from Illinois to Portland in August is currently the most expensive (average of $755). 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 May 20, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 20% 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 May 20, 2026.

The most flights from USIL to PDX are scheduled on a Wednesday (24 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (1 on average).

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

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 77 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 May 16, 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. Sunday 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 10m. Delta provides one of the quickest options available for as low as $319. 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 Hawaiian Airlines, which is currently one of the cheapest options available, starting at $52. Frontier flights start at $82 while deals on Spirit Airlines start at $86 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 (76%), Hawaiian Airlines( 76%).

  • What are the cheapest flights from Illinois to Portland?

    Looking for the cheapest flight from Illinois to Portland? While on average our users pay $786, our data indicates the cheapest price to be $126. The most popular route (Chicago O'Hare Intl - Portland), is priced around $305.

  • 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, October is the cheapest month in which you can book a flight from Illinois to Portland (average of $99). Flying from Illinois to Portland in August is currently the most expensive (average of $755). 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
Vancouver
Lincoln City
Longview
Lake Oswego
Hillsboro
Clackamas
Troutdale
Cannon Beach
Long Beach
McMinnville
Tigard
The Dalles
Wilsonville
Depoe Bay
Stevenson
Tillamook
Astoria
Gresham

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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 May 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$86Average$178FlexibilityNo cancel feeOn-time65%
Hawaiian AirlinesCheapest$124Average$252FlexibilityNo cancel feeOn-time85%
FrontierCheapest$150Average$248FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$194Average$318FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$199Average$461FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$200Average$383FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$227Average$358FlexibilityNo cancel feeOn-time63%

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