HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Illinois

$75+ 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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Portland to Illinois with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 September 15, 2025.

Round-trip from

$196
(Kiwi.com)

One-way from

$75
(Southwest)

Popular in

March

Cheapest in

January

Average price

$303

Good round-trip deal

$312 or less

Good one-way deal

$169 or less
From Portland to Illinois
Search Deals
One-way flight from Portland to Illinois
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($33 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 September 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

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 September 15, 2025.

This Frontier deal was found by Cheapflights users on 9/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/308:06 amPDX - ORD
1 stop11h 22mFrontier
Sat 10/412:22 pmORD - PDX
2 stops12h 12mFrontier
Deal found 9/15$195
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/212:07 pmPDX - ORD
1 stop7h 29mMultiple Airlines
Mon 10/610:32 amORD - PDX
1 stop27h 16mMultiple Airlines
Deal found 9/15$196
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1412:43 pmPDX - ORD
1 stop9h 10mFrontier
Tue 10/217:15 amORD - PDX
1 stop6h 33mFrontier
Deal found 9/14$199
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Sat 11/812:52 pmPDX - ORD
1 stop9h 20mFrontier
Wed 11/127:20 amORD - PDX
1 stop30h 36mFrontier
Deal found 9/14$200
This Booking.com deal was found by Cheapflights users on 9/15. 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.
Sun 10/2612:43 pmPDX - MDW
1 stop20h 33mFrontier
Fri 10/3112:30 pmMDW - PDX
1 stop25h 26mFrontier
Deal found 9/15$200
This Delta deal was found by Cheapflights users on 9/13. 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.
Thu 10/210:50 pmPDX - ORD
1 stop7h 15mDelta
Tue 10/76:05 pmORD - PDX
1 stop6h 35mDelta
Deal found 9/13$201
This Flightnetwork deal was found by Cheapflights users on 9/13. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2611:14 amPDX - ORD
1 stop9h 26mMultiple Airlines
Mon 9/296:15 amORD - PDX
1 stop6h 56mMultiple Airlines
Deal found 9/13$202
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/112:07 pmPDX - ORD
1 stop7h 25mSpirit Airlines
Fri 10/36:15 amORD - PDX
1 stop6h 56mSpirit Airlines
Deal found 9/14$203
This Frontier deal was found by Cheapflights users on 9/13. 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.
Fri 10/1712:43 pmPDX - ORD
1 stop10h 16mFrontier
Mon 10/206:50 amORD - PDX
1 stop6h 58mFrontier
Deal found 9/13$204
This Frontier deal was found by Cheapflights users on 9/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/17:15 amPDX - MDW
2 stops21h 56mFrontier
Fri 10/34:48 pmMDW - PDX
1 stop9h 24mFrontier
Deal found 9/14$204
This Frontier deal was found by Cheapflights users on 9/13. 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.
Mon 10/2012:43 pmPDX - ORD
1 stop10h 16mFrontier
Mon 10/276:50 amORD - PDX
1 stop6h 58mFrontier
Deal found 9/13$205
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Fri 10/3111:00 pmPDX - ORD
Nonstop4h 01mHawaiian Airlines
Sat 11/82:05 pmORD - PDX
Nonstop4h 36mHawaiian Airlines
Deal found 9/14$206

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 September 15, 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

Fri 1/16

7:00 am-1:04 pm

Nonstop4h 04m

Chicago O'Hare Intl

Mon 1/19

7:45 am-1:46 pm

1 stop8h 01m

$207

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 10/28

7:00 am-1:09 pm

Nonstop4h 09m

Chicago O'Hare Intl

Tue 11/4

2:05 pm-4:41 pm

Nonstop4h 36m

$231

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 10/28

7:00 am-1:09 pm

Nonstop4h 09m

Chicago O'Hare Intl

Tue 11/4

2:54 pm-8:46 pm

1 stop7h 52m

$241

PortlandSt. Louis

PDX - STL

PDXSTL

Portland

Sat 11/8

6:00 am-3:18 pm

1 stop7h 18m

Lambert-St Louis

Sat 11/15

7:00 am-12:38 pm

1 stop7h 38m

$248

PortlandSt. Louis

PDX - STL

PDXSTL

Portland

Fri 10/31

5:30 pm-3:18 pm

1 stop19h 48m

Lambert-St Louis

Mon 11/3

4:14 pm-8:37 pm

1 stop6h 23m

$248

PortlandSt. Louis

PDX - STL

PDXSTL

Portland

Tue 3/3

2:45 pm-11:56 pm

1 stop7h 11m

Lambert-St Louis

Wed 3/4

7:00 am-1:46 pm

1 stop8h 46m

$248

PortlandSt. Louis

PDX - STL

PDXSTL

Portland

Fri 10/24

1:25 pm-12:03 am

1 stop8h 38m

Lambert-St Louis

Tue 10/28

7:00 am-12:38 pm

1 stop7h 38m

$248

PortlandSt. Louis

PDX - STL

PDXSTL

Portland

Sat 11/8

6:00 am-3:18 pm

1 stop7h 18m

Lambert-St Louis

Sat 11/15

7:00 am-12:38 pm

1 stop7h 38m

$248

PortlandSt. Louis

PDX - STL

PDXSTL

Portland

Wed 11/26

4:05 pm-12:30 am

1 stop6h 25m

Lambert-St Louis

Tue 12/2

5:35 am-10:10 am

1 stop6h 35m

$249

PortlandSt. Louis

PDX - STL

PDXSTL

Portland

Mon 11/24

12:35 am-8:55 am

1 stop6h 20m

Lambert-St Louis

Tue 12/2

7:56 pm-12:05 am

1 stop6h 09m

$249

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 60 results
1
2
3
...
6

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 September 15, 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 September 15, 2025.

The most flights from PDX to USIL are scheduled on a Friday (32 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (23 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 September 15, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest, and United 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
10,000 reviews

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Southwest
8.0
Very good
4,242 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,929 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Frontier
5.8
Fair
3,172 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.0

Boarding

8.1

Crew

8.5

Food

7.1

Overall

8.0

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

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 Hawaiian Airlines, Southwest, and Alaska Airlines fly from Portland to Illinois in about 3h 55m. The time it takes to get you to your destination is usually consistent. Airlines will cover a distance of 1746 mi. Most flights are nonstop.

  • 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 $110. Southwest flights start at $114 while deals on Delta start at $115 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 (89%), Qatar Airways (87%), Air Canada (84%).

  • What are the cheapest flights from Portland to Illinois?

    On average you can expect to pay $814 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 $165.

  • 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Portland to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
Portland to Las Vegas flights
Portland to Los Angeles flights
Portland to Sky Harbor Intl flights
Portland to Denver flights
Portland to John F Kennedy Intl flights
Portland to Honolulu flights
Portland to O'Hare Intl flights
Portland to Ontario flights
Portland to Dallas/Fort Worth flights
Portland to Newark flights
Portland to San Diego flights
Portland to Orlando flights
Portland to Boston flights
Portland to Kahului flights
Portland to Santa Ana flights
Portland to LaGuardia flights
Portland to Kailua-Kona flights
Portland to Palm Springs flights
Portland to San Francisco flights
Portland to Hobby flights
Portland to Reagan-National flights
Boise to Seattle flights
Boise to Las Vegas flights
Portland to Salt Lake City flights
Boise to Sky Harbor Intl flights
Portland to Dulles Intl flights
Portland to Atlanta flights
Portland to Nashville flights
Portland to Miami flights
Portland to Austin flights
Portland to Oakland flights
Portland to New Orleans flights
Portland to Detroit flights
Portland to Lihue flights
Boise to Los Angeles flights
Portland to Burbank flights
Eugene to Los Angeles flights
Portland to San Jose flights
Portland to George Bush Intcntl flights
Boise to Dallas/Fort Worth flights
Boise to Denver flights
Portland to Midway flights
Portland to Minneapolis flights
Portland to Sacramento flights
Boise to O'Hare Intl flights
Portland to Tampa flights
Portland to Albuquerque flights
Portland to Philadelphia flights
Boise to San Diego flights
Boise to Portland flights

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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$93Average$200FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$268FlexibilityNo cancel feeOn-time62%
DeltaCheapest$123Average$333FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$125Average$286FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$195Average$452FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$200Average$348FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$226Average$471FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$233Average$413FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.