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$63+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PDX
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
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 October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$123
(Kiwi.com)

One-way from

$63
(Trip.com)

Popular in

December

Cheapest in

January

Average price

$314

Good round-trip deal

$263 or less

Good one-way deal

$118 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. 4% potential increase in price ($14 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 October 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/37:43 pmSTL - PDX
1 stop18h 13mFrontier
Fri 12/512:55 pmPDX - STL
1 stop19h 19mFrontier
Deal found 10/28$124
This Frontier deal was found by Cheapflights users on 10/28. 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 12/41:16 pmSTL - PDX
1 stop22h 18mFrontier
Thu 12/1112:51 pmPDX - STL
1 stop19h 23mFrontier
Deal found 10/28$151
This Frontier deal was found by Cheapflights users on 10/28. 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.
Sat 11/87:45 pmSTL - PDX
1 stop18h 11mFrontier
Sat 11/1512:52 pmPDX - STL
1 stop18h 15mFrontier
Deal found 10/28$177
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 12/207:43 pmSTL - PDX
1 stop18h 00mFrontier
Sun 1/412:47 pmPDX - STL
1 stop19h 15mFrontier
Deal found 10/27$179
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 12/207:43 pmSTL - PDX
1 stop18h 00mFrontier
Thu 1/112:47 pmPDX - STL
1 stop19h 15mFrontier
Deal found 10/27$185
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 12/227:43 pmSTL - PDX
1 stop18h 00mFrontier
Thu 1/112:47 pmPDX - STL
1 stop19h 15mFrontier
Deal found 10/27$190
This Booking.com deal was found by Cheapflights users on 10/28. 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 11/147:45 pmSTL - PDX
1 stop18h 11mFrontier
Mon 11/173:26 pmPDX - STL
1 stop15h 41mFrontier
Deal found 10/28$194
This Mytrip deal was found by Cheapflights users on 10/27. 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.
Sat 11/87:45 pmSTL - PDX
1 stop18h 11mFrontier
Tue 11/111:26 pmPDX - STL
1 stop17h 41mFrontier
Deal found 10/27$205
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 12/227:43 pmSTL - PDX
1 stop18h 00mFrontier
Sun 1/410:24 pmPDX - STL
2 stops19h 43mFrontier
Deal found 10/27$209
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 12/69:06 pmORD - PDX
1 stop21h 31mMultiple Airlines
Sat 12/139:48 amPDX - ORD
1 stop12h 25mMultiple Airlines
Deal found 10/29$209
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/117:00 amORD - PDX
1 stop30h 56mFrontier
Sun 1/1811:29 amPDX - ORD
1 stop21h 09mFrontier
Deal found 10/28$210
This CheapOair deal was found by Cheapflights users on 10/27. 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.
Fri 11/77:45 pmSTL - PDX
1 stop18h 11mFrontier
Tue 11/111:26 pmPDX - STL
1 stop17h 41mFrontier
Deal found 10/27$212

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 October 29, 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

Mon 11/17

1:47 pm-8:47 pm

1 stop9h 00m

Portland

Wed 11/19

11:15 pm-8:54 am

1 stop7h 39m

$247

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 12/4

9:05 am-11:48 am

Nonstop4h 43m

Portland

Mon 12/8

10:10 am-9:07 pm

1 stop8h 57m

$247

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Wed 12/17

2:05 pm-4:48 pm

Nonstop4h 43m

Portland

Tue 12/30

11:00 pm-5:02 am

Nonstop4h 02m

$247

ChicagoPortland

ORD - PDX

ORDPDX

Chicago O'Hare Intl

Thu 12/4

2:05 pm-4:48 pm

Nonstop4h 43m

Portland

Sun 12/7

4:38 pm-6:21 am

1 stop11h 43m

$247

St. LouisPortland

STL - PDX

STLPDX

Lambert-St Louis

Mon 1/12

6:45 am-12:33 pm

1 stop7h 48m

Portland

Thu 1/15

12:59 pm-10:00 pm

1 stop7h 01m

$249

St. LouisPortland

STL - PDX

STLPDX

Lambert-St Louis

Thu 11/20

6:34 am-12:34 pm

1 stop8h 00m

Portland

Thu 11/27

5:30 am-3:05 pm

1 stop7h 35m

$249

St. LouisPortland

STL - PDX

STLPDX

Lambert-St Louis

Sat 4/11

6:30 pm-12:19 am

1 stop7h 49m

Portland

Sat 4/18

5:15 am-12:43 pm

1 stop5h 28m

$249

St. LouisPortland

STL - PDX

STLPDX

Lambert-St Louis

Tue 12/9

2:20 pm-6:14 pm

1 stop5h 54m

Portland

Wed 12/10

12:32 am-9:10 am

1 stop6h 38m

$249

St. LouisPortland

STL - PDX

STLPDX

Lambert-St Louis

Thu 4/23

7:00 am-1:46 pm

1 stop8h 46m

Portland

Sun 4/26

10:40 am-11:55 pm

1 stop11h 15m

$249

St. LouisPortland

STL - PDX

STLPDX

Lambert-St Louis

Mon 1/19

3:31 pm-8:32 pm

1 stop7h 01m

Portland

Wed 1/21

6:00 am-2:48 pm

1 stop6h 48m

$249

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

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 $143). 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 October 29, 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.

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 43m. Delta provides one of the quickest options available for as low as $247. 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 $118. Alaska Airlines flights start at $118 while deals on Delta start at $119 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 $1,348, our data indicates the cheapest price to be $115. The most popular route (Chicago O'Hare Intl - Portland), is priced around $182.

  • 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 $143). 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
Gresham
Tillamook
Troutdale

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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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$86Average$184FlexibilityNo cancel feeOn-time65%
DeltaCheapest$88Average$372FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$110Average$220FlexibilityNo cancel feeOn-time62%
Hawaiian AirlinesCheapest$134Average$284FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$198Average$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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