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$61+ 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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PDX
nov. 19 — nov. 261
mié. 11/19
mié. 11/26
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 octubre 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$210
(Kiwi.com)

One-way from

$61
(Trip.com)

Popular in

December

Cheapest in

January

Average price

$313

Good round-trip deal

$268 or less

Good one-way deal

$128 or less
Provider with most accurate pricing for Chicago (CHI)-Portland flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Portland flights.
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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. 3% potential increase in price ($11 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 October 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 octubre 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/89:22 pmORD - PDX
1 stop17h 01mMultiple Airlines
sáb. 11/1512:52 pmPDX - ORD
1 stop8h 37mMultiple Airlines
Deal found 10/18$210
This Kiwi.com deal was found by Cheapflights users on 10/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/254:58 pmORD - PDX
1 stop22h 10mMultiple Airlines
sáb. 12/69:48 amPDX - ORD
1 stop12h 25mMultiple Airlines
Deal found 10/18$211
This Kiwi.com deal was found by Cheapflights users on 10/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/81:37 pmMDW - PDX
2 stops24h 19mFrontier
sáb. 11/1512:52 pmPDX - MDW
1 stop20h 38mFrontier
Deal found 10/18$212
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/136:00 amORD - PDX
1 stop7h 56mMultiple Airlines
dom. 11/167:57 pmPDX - ORD
1 stop7h 35mMultiple Airlines
Deal found 10/19$212
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/139:39 pmMDW - PDX
2 stops18h 52mFrontier
dom. 11/163:26 pmPDX - MDW
1 stop18h 04mFrontier
Deal found 10/19$214
This Mytrip deal was found by Cheapflights users on 10/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/316:00 amORD - PDX
1 stop7h 56mFrontier
dom. 11/23:26 pmPDX - ORD
1 stop7h 23mFrontier
Deal found 10/17$214
This Kiwi.com deal was found by Cheapflights users on 10/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/3112:30 pmMDW - PDX
1 stop25h 26mFrontier
dom. 11/27:57 pmPDX - MDW
2 stops37h 41mFrontier
Deal found 10/17$215
This Booking.com deal was found by Cheapflights users on 10/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/712:30 pmMDW - PDX
1 stop25h 26mFrontier
dom. 11/93:26 pmPDX - MDW
1 stop18h 04mFrontier
Deal found 10/19$216
This Expedia deal was found by Cheapflights users on 10/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/25:00 amORD - PDX
1 stop7h 56mMultiple Airlines
mar. 12/167:04 amPDX - ORD
Nonstop4h 05mMultiple Airlines
Deal found 10/18$216
This American Airlines deal was found by Cheapflights users on 10/19. 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.
mié. 11/128:14 amORD - PDX
Nonstop4h 34mAmerican Airlines
sáb. 11/151:26 pmPDX - ORD
Nonstop4h 15mAmerican Airlines
Deal found 10/19$217
This Kiwi.com deal was found by Cheapflights users on 10/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/3111:53 amORD - PDX
2 stops26h 03mFrontier
lun. 11/33:26 pmPDX - ORD
1 stop22h 13mFrontier
Deal found 10/18$218
This Southwest deal was found by Cheapflights users on 10/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/114:50 pmMDW - PDX
Nonstop4h 30mSouthwest
lun. 12/1510:05 amPDX - MDW
1 stop10h 05mSouthwest
Deal found 10/19$219

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 octubre 20, 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

ORD - PDX

ORDPDX

Chicago O'Hare Intl

mié. 11/12

2:54 pm-8:46 pm

1 stop7h 52m

Portland

sáb. 11/15

11:00 pm-5:01 am

Nonstop4h 01m

$227

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

jue. 12/11

5:25 am-10:50 am

1 stop7h 25m

Portland

lun. 12/15

2:05 pm-5:05 am

1 stop13h 00m

$228

St. LouisPortland

STL - PDX

STLPDX

Lambert-St Louis

lun. 11/10

7:47 pm-8:31 am

2 stops14h 44m

Portland

sáb. 11/15

5:26 pm-8:55 am

2 stops13h 29m

$236

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

mié. 12/3

8:59 pm-9:47 am

1 stop14h 48m

Portland

mié. 12/10

9:37 am-10:30 pm

1 stop10h 53m

$236

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

mié. 12/3

8:59 pm-9:47 am

1 stop14h 48m

Portland

mar. 12/9

10:40 am-10:30 pm

1 stop9h 50m

$236

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

jue. 11/13

9:50 pm-12:20 am

Nonstop4h 30m

Portland

dom. 11/16

6:30 am-12:25 pm

Nonstop3h 55m

$237

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

sáb. 11/15

1:47 pm-8:47 pm

1 stop9h 00m

Portland

mar. 11/18

11:53 am-11:40 pm

1 stop9h 47m

$237

ChicagoPortland

MDW - PDX

MDWPDX

Chicago Midway

mié. 12/3

1:50 pm-8:52 pm

1 stop9h 02m

Portland

lun. 12/8

12:32 am-9:19 am

1 stop6h 47m

$237

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

mié. 11/12

7:40 pm-11:58 pm

1 stop6h 18m

Portland

vie. 11/14

12:35 am-10:24 am

1 stop7h 49m

$237

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

sáb. 12/13

8:55 am-4:43 pm

1 stop9h 48m

Portland

lun. 12/15

7:04 am-1:09 pm

Nonstop4h 05m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/19

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 $142). Flying from Illinois to Portland in May is currently the most expensive (average of $199). 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 octubre 20, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 32% 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. Sunday 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 octubre 20, 2025.

The most flights from USIL to PDX are scheduled on a Friday (24 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (18 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 7h 25m. Alaska Airlines provides one of the quickest options available for as low as $228. There are 1746 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 $112. Hawaiian Airlines flights start at $115 while deals on Frontier start at $115 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: Alaska Airlines (84%), Hawaiian Airlines (84%), Air Canada( 81%).

  • What are the cheapest flights from Illinois to Portland?

    Looking for the cheapest flight from Illinois to Portland? While on average our users pay $1,268, our data indicates the cheapest price to be $115. The most popular route (Chicago O'Hare Intl - Portland), is priced around $163.

  • 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 $142). Flying from Illinois to Portland in May is currently the most expensive (average of $199). 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
Lake Oswego
Beaverton
McMinnville
Hillsboro
Cannon Beach
Long Beach
Longview
Tigard
The Dalles
Depoe Bay
Stevenson
Wilsonville
Pacific City
Tillamook
Gresham
Troutdale

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 octubre 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$86Average$184FlexibilityNo cancel feeOn-time65%
FrontierCheapest$110Average$220FlexibilityNo cancel feeOn-time62%
DeltaCheapest$123Average$328FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$134Average$284FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$196Average$298FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$213Average$460FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$226Average$420FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$238Average$432FlexibilityNo cancel feeOn-time63%

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