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Illinois

$69+ Cheap flights from Portland (PDX) to Illinois

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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Jul 7 — Jul 141
Mon 7/7
Mon 7/14
1 adult, Economy
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Cheap flight deals from Portland to Illinois

Keep the following information in mind while searching for Portland to Illinois flight deals. Data was last updated July 2, 2025.

Round-trip from

$216
(CheapOair)

One-way from

$69
(Priceline)

Popular in

March

Cheapest in

January

Average price

$317

Good round-trip deal

$320 or less

Good one-way deal

$182 or less
From Portland to Illinois
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One-way flight from Portland to Illinois
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Highest demand for flights based on searches. 10% potential increase in price ($38 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Portland to Illinois.
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Price to beat on a one-way flight from Portland to Illinois.
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Find flight deals from Portland to Illinois

Cheapest flights from Portland to Illinois
Explore the most affordable flight options available from Portland to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 2, 2025.

This Priceline deal was found by Cheapflights users on 6/30. 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.
Mon 6/3011:00 amPDX - ORD
1 stop7h 56mFrontier
Thu 7/35:40 amORD - PDX
1 stop6h 38mFrontier
Deal found 6/30$215
This CheapOair deal was found by Cheapflights users on 7/1. 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.
Tue 7/153:10 pmPDX - ORD
1 stop12h 53mSpirit Airlines
Sat 7/197:49 pmORD - PDX
1 stop15h 29mSpirit Airlines
Deal found 7/1$216
This Expedia deal was found by Cheapflights users on 6/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/3012:25 pmPDX - ORD
1 stop9h 45mMultiple Airlines
Tue 8/57:00 amORD - PDX
Nonstop4h 25mMultiple Airlines
Deal found 6/29$217
This Southwest deal was found by Cheapflights users on 7/1. 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 8/235:10 amPDX - MDW
2 stops9h 25mSouthwest
Sun 8/318:20 pmMDW - PDX
Nonstop4h 15mSouthwest
Deal found 7/1$218
This FlightHub deal was found by Cheapflights users on 6/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/245:50 pmPDX - MDW
1 stop15h 51mFrontier
Fri 8/112:35 pmMDW - PDX
1 stop24h 55mFrontier
Deal found 6/30$219
This United Airlines deal was found by Cheapflights users on 7/1. 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.
Thu 8/287:35 pmPDX - ORD
1 stop7h 48mUnited Airlines
Sun 8/311:05 pmORD - PDX
Nonstop4h 20mUnited Airlines
Deal found 7/1$224
This American Airlines deal was found by Cheapflights users on 6/30. 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 8/271:20 pmPDX - ORD
Nonstop3h 58mAmerican Airlines
Tue 9/212:10 pmORD - PDX
Nonstop4h 19mAmerican Airlines
Deal found 6/30$225
This Alaska Airlines deal was found by Cheapflights users on 7/2. 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.
Fri 10/3110:00 pmPDX - ORD
1 stop6h 22mAlaska Airlines
Mon 11/36:00 amORD - PDX
1 stop8h 29mAlaska Airlines
Deal found 7/2$234
This Hawaiian Airlines deal was found by Cheapflights users on 6/30. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/55:35 pmPDX - ORD
Nonstop4h 04mHawaiian Airlines
Sun 8/107:00 amORD - PDX
Nonstop4h 25mHawaiian Airlines
Deal found 6/30$238
This Delta deal was found by Cheapflights users on 6/30. 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.
Fri 8/1512:46 amPDX - MDW
1 stop6h 04mDelta
Tue 8/261:43 pmMDW - PDX
1 stop9h 16mDelta
Deal found 6/30$245
This Gotogate deal was found by Cheapflights users on 6/30. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/256:35 amPDX - STL
1 stop24h 36mFrontier
Mon 7/287:29 pmSTL - PDX
1 stop6h 47mFrontier
Deal found 6/30$255
This Expedia deal was found by Cheapflights users on 7/1. 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.
Sat 10/41:25 pmPDX - STL
1 stop8h 34mMultiple Airlines
Sun 10/127:52 pmSTL - PDX
1 stop6h 24mMultiple Airlines
Deal found 7/1$276

Cheapflights Fare Finder

Customize your flight search to find flights from Portland to Illinois 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 2, 2025.
Use the filters below to find and compare flights from Portland to Illinois that are best for you.

Fly from

Portland

Fly to

Illinois

Route

Depart

Return

Price

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 7/15

3:10 pm-6:03 am

1 stop12h 53m

Chicago O'Hare Intl

Sat 7/19

7:49 pm-9:18 am

1 stop15h 29m

$216

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 7/30

12:25 pm-12:10 am

1 stop9h 45m

Chicago O'Hare Intl

Tue 8/5

7:00 am-9:25 am

Nonstop4h 25m

$217

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 8/2

6:35 am-12:32 am

1 stop15h 57m

Chicago O'Hare Intl

Sun 8/3

9:56 pm-12:51 pm

1 stop16h 55m

$218

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 8/23

5:10 am-4:35 pm

2 stops9h 25m

Chicago Midway

Sun 8/31

8:20 pm-10:35 pm

Nonstop4h 15m

$218

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 7/24

5:50 pm-11:41 am

1 stop15h 51m

Chicago Midway

Fri 8/1

12:35 pm-11:30 am

1 stop24h 55m

$219

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 8/28

7:35 pm-5:23 am

1 stop7h 48m

Chicago O'Hare Intl

Sun 8/31

1:05 pm-3:25 pm

Nonstop4h 20m

$224

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 8/27

1:20 pm-7:18 pm

Nonstop3h 58m

Chicago O'Hare Intl

Tue 9/2

12:10 pm-2:29 pm

Nonstop4h 19m

$225

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 10/31

10:15 am-8:58 pm

1 stop8h 43m

Chicago O'Hare Intl

Mon 11/3

7:30 am-2:39 pm

1 stop9h 09m

$234

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 8/13

5:35 pm-11:39 pm

Nonstop4h 04m

Chicago O'Hare Intl

Tue 8/26

6:20 am-12:24 pm

1 stop8h 04m

$235

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 8/5

5:35 pm-11:39 pm

Nonstop4h 04m

Chicago O'Hare Intl

Sun 8/10

7:00 am-9:25 am

Nonstop4h 25m

$238

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Showing 1-10 of 55 results
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Best time to book a flight from Portland to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Portland 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 Portland to Illinois

What is the cheapest month to book a flight from Portland to Illinois?

Currently, August is the cheapest month in which you can book a flight from Portland to Illinois (average of $245). Flying from Portland to Illinois in March is currently the most expensive (average of $321). 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 PDX to IL?

Find hourly flight availability from Portland to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 2, 2025.

When flying from Portland to Illinois, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Portland to Illinois

Explore weekly flight availability from Portland to Illinois. 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 2, 2025.

The most flights from PDX to USIL are scheduled on a Monday (28 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (9 on average).

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Illinois. Reviews last updated July 2, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest, and Delta from Portland to Illinois. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Entertainment

7.1

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Entertainment

7.1

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,272 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Entertainment

7.1

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,983 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Entertainment

7.1

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.8
Good
2,540 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Entertainment

7.1

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,861 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Crew

8.5

Comfort

7.8

Entertainment

7.1

Overall

8.0

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Related info for your journey

Find useful and relevant information for your journey from Portland to Illinois. 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 from for flights from Portland to Illinois?

    Located just 6.0 mi from the city center, Portland (PDX) is the airport most travelers will use when flying to Illinois from Portland.

  • What are the cheapest airlines to fly from Portland to Illinois one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $69. Spirit Airlines flights start at $91 while deals on Alaska Airlines start at $112 one-way.

  • What are the most popular routes from Portland to Illinois?

    When deciding which route to take from Portland to Illinois consider Portland - Chicago O'Hare Intl, Portland - Chicago Midway or Portland - Lambert-St Louis as they are the most popular.

  • What are the most reliable airlines from Portland to Illinois?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Portland to Illinois on time: United Airlines (83%), SWISS (83%), Brussels Airlines (82%).

  • What are the cheapest flights from Portland to Illinois?

    On average you can expect to pay $1,168 for a flight from Portland to Illinois. The cheapest flight overall is $124 while the most popular route, (Portland - Chicago O'Hare Intl) is currently priced at $162.

  • Can I find deals for flights from Portland to Illinois that include hotel bookings?

    Yes. In addition to deals on Portland to Illinois flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Illinois?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Illinois.

  • Can I find deals for business class flights from Portland to Illinois?

    Yes. Cheapflights offers flight deals from Portland to Illinois 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 Portland to Illinois?

    Currently, August is the cheapest month in which you can book a flight from Portland to Illinois (average of $245). Flying from Portland to Illinois in March is currently the most expensive (average of $321). 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.

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Alternative routes for Portland to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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Top 8 airlines flying from Portland to Illinois

Discover the top 8 airlines that operate flights from Portland to Illinois. 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 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$87Average$146FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$233FlexibilityNo cancel feeOn-time62%
DeltaCheapest$123Average$288FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$187Average$334FlexibilityNo cancel feeOn-time75%
Hawaiian AirlinesCheapest$202Average$293FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$217Average$470FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$227Average$497FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$249Average$434FlexibilityNo cancel feeOn-time63%

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