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$62+ 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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Nov 16 — Nov 231
Sun 11/16
Sun 11/23
1 adult, Economy
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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 October 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/612:52 pmPDX - ORD
1 stop9h 23mFrontier
Sun 11/910:43 pmORD - PDX
2 stops23h 16mFrontier
Deal found 10/15$224
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2512:47 pmPDX - ORD
1 stop9h 25mMultiple Airlines
Tue 12/306:44 pmORD - PDX
1 stop24h 18mMultiple Airlines
Deal found 10/15$225
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1312:52 pmPDX - ORD
1 stop9h 23mFrontier
Mon 11/176:00 amORD - PDX
1 stop7h 56mFrontier
Deal found 10/17$226
This Alaska Airlines deal was found by Cheapflights users on 10/15. 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.
Fri 11/1411:00 pmPDX - ORD
Nonstop4h 01mAlaska Airlines
Sat 11/152:05 pmORD - PDX
Nonstop4h 36mAlaska Airlines
Deal found 10/15$227
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/73:26 pmPDX - ORD
1 stop6h 49mFrontier
Mon 11/106:00 amORD - PDX
1 stop7h 56mFrontier
Deal found 10/17$228
This Kiwi.com deal was found by Cheapflights users on 10/14. 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.
Tue 10/213:28 pmPDX - ORD
2 stops23h 12mFrontier
Fri 11/146:00 amORD - PDX
1 stop7h 56mFrontier
Deal found 10/14$229
This Expedia deal was found by Cheapflights users on 10/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3111:00 pmPDX - ORD
Nonstop4h 01mMultiple Airlines
Sun 11/25:00 amORD - PDX
1 stop7h 56mMultiple Airlines
Deal found 10/15$231
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/143:26 pmPDX - ORD
1 stop30h 03mMultiple Airlines
Fri 11/2110:24 amORD - PDX
1 stop8h 54mMultiple Airlines
Deal found 10/15$232
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/192:31 pmPDX - ORD
1 stop7h 28mAlaska Airlines
Sun 11/237:00 amORD - PDX
Nonstop4h 39mAlaska Airlines
Deal found 10/15$233
This Orbitz deal was found by Cheapflights users on 10/16. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1312:52 pmPDX - ORD
1 stop9h 23mMultiple Airlines
Thu 11/207:00 amORD - PDX
Nonstop4h 39mMultiple Airlines
Deal found 10/16$234
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3012:52 pmPDX - ORD
1 stop9h 51mFrontier
Mon 11/36:40 amORD - PDX
2 stops31h 16mFrontier
Deal found 10/15$235
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/122:31 pmPDX - ORD
1 stop7h 28mAlaska Airlines
Wed 11/199:20 amORD - PDX
1 stop9h 38mAlaska Airlines
Deal found 10/17$236

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 October 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$224
(Kiwi.com)

One-way from

$62
(Trip.com)

Popular in

March

Cheapest in

August

Average price

$334

Good round-trip deal

$328 or less

Good one-way deal

$171 or less
Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Chicago (CHI) flights.
Search Deals
From Portland to Illinois
Search Deals
One-way flight from Portland to Illinois
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($35 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Portland to Illinois.
Search Deals
Price to beat on a one-way flight from Portland to Illinois.
Search Deals

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 October 17, 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

Thu 11/13

11:00 pm-5:01 am

Nonstop4h 01m

Chicago O'Hare Intl

Sun 11/16

7:00 am-9:39 am

Nonstop4h 39m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 12/5

10:50 am-4:52 pm

Nonstop4h 02m

Chicago O'Hare Intl

Sun 12/7

9:05 am-11:48 am

Nonstop4h 43m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 3/10

7:00 am-1:04 pm

Nonstop4h 04m

Chicago O'Hare Intl

Wed 3/11

7:45 am-12:36 pm

1 stop6h 51m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 11/8

11:39 am-8:23 pm

1 stop6h 44m

Chicago O'Hare Intl

Sat 11/15

5:29 pm-10:51 pm

1 stop7h 22m

$237

PortlandChicago

PDX - MDW

PDXMDW

Portland

Thu 12/11

6:15 am-12:10 pm

Nonstop3h 55m

Chicago Midway

Sun 12/14

9:50 pm-12:20 am

Nonstop4h 30m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 2/17

7:00 am-5:50 pm

1 stop8h 50m

Chicago O'Hare Intl

Fri 2/27

2:05 pm-4:39 pm

Nonstop4h 34m

$237

PortlandChicago

PDX - MDW

PDXMDW

Portland

Mon 3/9

12:55 am-8:54 am

1 stop5h 59m

Chicago Midway

Wed 3/11

9:20 am-4:51 pm

1 stop9h 31m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 12/5

1:34 pm-11:59 pm

1 stop8h 25m

Chicago O'Hare Intl

Tue 12/9

2:05 pm-4:48 pm

Nonstop4h 43m

$237

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 11/7

12:40 am-10:30 am

1 stop7h 50m

Chicago Midway

Sat 11/8

3:00 pm-8:26 pm

1 stop7h 26m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 2/18

8:40 am-5:50 pm

1 stop7h 10m

Chicago O'Hare Intl

Fri 2/27

2:05 pm-4:39 pm

Nonstop4h 34m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/15

Showing 1-10 of 60 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 $120). Flying from Portland to Illinois in March is currently the most expensive (average of $256). 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 October 17, 2025.

It’s typically best to fly out from Portland to Illinois in the afternoon. Doing so could potentially save you 36% on the flight price compared to flying at noon, which is usually more expensive.

What is the cheapest day to fly from Portland to Illinois?

Use this chart to determine the cheapest time to fly round-trip from Portland to Illinois. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Portland to Illinois flight should consider departing on Saturday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 October 17, 2025.

The most flights from PDX to USIL are scheduled on a Wednesday (28 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (19 on average).

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

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 October 17, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest, and Hawaiian Airlines 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
11,105 reviews

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Alaska Airlines
8.0
Very good
11,105 reviews
Alaska Airlines
8.0
Very good
11,105 reviews

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Southwest
8.0
Very good
4,242 reviews
Alaska Airlines
8.0
Very good
11,105 reviews

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Hawaiian Airlines
7.8
Good
2,781 reviews
Alaska Airlines
8.0
Very good
11,105 reviews

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
United Airlines
7.4
Good
8,983 reviews
Alaska Airlines
8.0
Very good
11,105 reviews

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
American Airlines
7.2
Good
11,039 reviews
Alaska Airlines
8.0
Very good
11,105 reviews

Comfort

7.8

Boarding

8.1

Crew

8.5

Entertainment

7.0

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

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.

  • How long is the flight from Portland to Illinois?

    Airlines like Alaska Airlines, United Airlines, and Delta fly from Portland to Illinois in about 4h 01m. The time it takes to get you to your destination can typically vary by up to 1h 58m. Airlines will cover a distance of 1733 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    To fly one-way, consider booking your trip with United Airlines, which is currently one of the cheapest options available, starting at $114. Alaska Airlines flights start at $118 while deals on Southwest start at $118 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: Brussels Airlines (92%), SWISS (82%), Alaska Airlines (82%).

  • What are the cheapest flights from Portland to Illinois?

    On average you can expect to pay $813 for a flight from Portland to Illinois. The cheapest flight overall is $115 while the most popular route, (Portland - Chicago O'Hare Intl) is currently priced at $152.

  • 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 $120). Flying from Portland to Illinois in March is currently the most expensive (average of $256). 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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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 October 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$94Average$274FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$119Average$194FlexibilityNo cancel feeOn-time65%
DeltaCheapest$123Average$333FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$125Average$284FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$192Average$456FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$197Average$322FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$224Average$463FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$246Average$400FlexibilityNo cancel feeOn-time63%

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