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$60+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
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 November 26, 2025.

This Frontier deal was found by Cheapflights users on 11/26. 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.
Sun 12/710:29 amPDX - STL
1 stop7h 47mFrontier
Sun 12/1410:44 pmSTL - PDX
1 stop11h 52mFrontier
Deal found 11/26$232
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 12/1212:55 pmPDX - STL
1 stop19h 19mFrontier
Wed 12/177:43 pmSTL - PDX
1 stop18h 00mFrontier
Deal found 11/24$236
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 12/1112:51 pmPDX - STL
1 stop19h 23mFrontier
Wed 12/177:43 pmSTL - PDX
1 stop18h 00mFrontier
Deal found 11/24$240
This Alaska Airlines deal was found by Cheapflights users on 11/25. 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.
Sat 12/139:44 pmPDX - ORD
1 stop6h 37mAlaska Airlines
Wed 12/178:00 amORD - PDX
1 stop7h 50mAlaska Airlines
Deal found 11/25$243
This Alaska Airlines deal was found by Cheapflights users on 11/25. 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 12/107:04 amPDX - ORD
Nonstop4h 05mAlaska Airlines
Mon 12/158:59 pmORD - PDX
1 stop14h 48mAlaska Airlines
Deal found 11/25$244
This Southwest deal was found by Cheapflights users on 11/25. 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.
Wed 12/106:15 amPDX - MDW
Nonstop3h 55mSouthwest
Thu 12/255:15 amMDW - PDX
1 stop8h 10mSouthwest
Deal found 11/25$244
This Expedia deal was found by Cheapflights users on 11/25. 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 12/1212:55 pmPDX - ORD
1 stop9h 17mMultiple Airlines
Thu 12/187:00 amORD - PDX
Nonstop4h 50mMultiple Airlines
Deal found 11/25$245
This Expedia deal was found by Cheapflights users on 11/25. 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 12/107:44 pmPDX - ORD
1 stop8h 37mMultiple Airlines
Sun 12/147:00 amORD - PDX
1 stop6h 56mMultiple Airlines
Deal found 11/25$246
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 12/139:48 amPDX - ORD
1 stop12h 25mFrontier
Tue 12/164:22 pmORD - PDX
2 stops45h 21mFrontier
Deal found 11/24$247
This Southwest deal was found by Cheapflights users on 11/24. 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 12/136:00 amPDX - MDW
1 stop12h 10mSouthwest
Tue 1/65:05 amMDW - PDX
1 stop7h 45mSouthwest
Deal found 11/24$249
This Delta deal was found by Cheapflights users on 11/25. 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.
Mon 12/1512:32 amPDX - STL
1 stop6h 38mDelta
Wed 12/176:00 amSTL - PDX
1 stop8h 54mDelta
Deal found 11/25$249
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 12/139:48 amPDX - ORD
1 stop12h 25mFrontier
Thu 12/189:33 pmORD - PDX
1 stop24h 17mFrontier
Deal found 11/24$250

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 November 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$232
(Frontier)

One-way from

$60
(Trip.com)

Popular in

March

Cheapest in

August

Average price

$391

Good round-trip deal

$301 or less

Good one-way deal

$197 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. 7% potential increase in price ($27 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 November 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 November 26, 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 - MDW

PDXMDW

Portland

Wed 2/4

12:40 am-9:08 am

1 stop6h 28m

Chicago Midway

Wed 2/11

1:51 pm-8:32 pm

1 stop8h 41m

$247

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 2/7

9:55 am-8:30 pm

2 stops8h 35m

Chicago Midway

Sat 2/14

2:05 pm-10:30 pm

2 stops10h 25m

$247

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 2/4

12:40 am-9:08 am

1 stop6h 28m

Chicago Midway

Tue 2/17

1:49 pm-8:30 pm

1 stop8h 41m

$247

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sun 2/1

6:45 am-12:40 pm

Nonstop3h 55m

Chicago Midway

Thu 2/5

5:00 pm-11:00 pm

1 stop8h 00m

$247

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 12/13

6:00 am-8:10 pm

1 stop12h 10m

Chicago Midway

Tue 1/6

5:05 am-10:50 am

1 stop7h 45m

$249

PortlandSt. Louis

PDX - STL

PDXSTL

Portland

Tue 12/9

8:30 am-4:28 pm

1 stop5h 58m

Lambert-St Louis

Sat 12/13

4:37 pm-9:15 pm

1 stop6h 38m

$251

PortlandSt. Louis

PDX - STL

PDXSTL

Portland

Wed 12/10

5:30 am-1:30 pm

1 stop6h 00m

Lambert-St Louis

Sat 12/13

5:00 pm-10:10 pm

1 stop7h 10m

$251

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 12/10

8:00 am-5:10 pm

1 stop7h 10m

Chicago Midway

Thu 12/25

5:15 am-11:25 am

1 stop8h 10m

$253

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 1/8

1:38 pm-11:50 pm

1 stop8h 12m

Chicago O'Hare Intl

Sun 1/11

6:06 pm-10:46 pm

1 stop6h 40m

$256

PortlandChicago

PDX - MDW

PDXMDW

Portland

Wed 1/21

12:40 am-9:08 am

1 stop6h 28m

Chicago Midway

Sun 1/25

1:49 pm-8:32 pm

1 stop8h 43m

$278

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/23

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 $242). 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 November 26, 2025.

It’s typically best to fly out from Portland to Illinois in the afternoon. Doing so could potentially save you 34% on the flight price compared to flying in the morning, 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 Tuesday at noon 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 November 26, 2025.

The most flights from PDX to USIL are scheduled on a Wednesday (20 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (6 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 November 26, 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
11,354 reviews

Crew

8.5

Entertainment

7.0

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

LAX - LIH

The staff were exceptional! They all were kind, accommodating, and professional.
Alaska Airlines
8.0
Very good
11,354 reviews
Alaska Airlines
8.0
Very good
11,354 reviews

Crew

8.5

Entertainment

7.0

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

LAX - LIH

The staff were exceptional! They all were kind, accommodating, and professional.
Southwest
8.0
Very good
4,254 reviews
Alaska Airlines
8.0
Very good
11,354 reviews

Crew

8.5

Entertainment

7.0

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

LAX - LIH

The staff were exceptional! They all were kind, accommodating, and professional.
Hawaiian Airlines
7.8
Good
2,814 reviews
Alaska Airlines
8.0
Very good
11,354 reviews

Crew

8.5

Entertainment

7.0

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

LAX - LIH

The staff were exceptional! They all were kind, accommodating, and professional.
United Airlines
7.4
Good
9,046 reviews
Alaska Airlines
8.0
Very good
11,354 reviews

Crew

8.5

Entertainment

7.0

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

LAX - LIH

The staff were exceptional! They all were kind, accommodating, and professional.
American Airlines
7.2
Good
11,038 reviews
Alaska Airlines
8.0
Very good
11,354 reviews

Crew

8.5

Entertainment

7.0

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Nov 2025

LAX - LIH

The staff were exceptional! They all were kind, accommodating, and professional.

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 Delta, Southwest, and United Airlines fly from Portland to Illinois in about 5h 58m. The time it takes to get you to your destination can typically vary by up to 2h 37m. Airlines will cover a distance of 1702 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 (90%), SWISS (86%), American Airlines (83%).

  • What are the cheapest flights from Portland to Illinois?

    On average you can expect to pay $933 for a flight from Portland to Illinois. The cheapest flight overall is $118 while the most popular route, (Portland - Chicago O'Hare Intl) is currently priced at $224.

  • 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 $242). 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 November 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$94Average$248FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$119Average$184FlexibilityNo cancel feeOn-time65%
DeltaCheapest$123Average$333FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$125Average$284FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$194Average$452FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$217Average$346FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$219Average$457FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$238Average$386FlexibilityNo cancel feeOn-time63%

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