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$67+ 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 4/3. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap 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 January 21, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/20. 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 2/2710:18 pm
PDX
-
STL
1 stop17h 28m
Frontier
Sun 3/110:11 pm
STL
-
PDX
1 stop22h 10m
Frontier
Deal found 1/20$197
This United Airlines deal was found by Cheapflights users on 1/21. 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.
Fri 2/201:40 pm
PDX
-
ORD
1 stop7h 46m
United Airlines
Tue 3/312:45 pm
ORD
-
PDX
Nonstop4h 42m
United Airlines
Deal found 1/21$217
This Delta deal was found by Cheapflights users on 1/20. 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.
Sat 2/146:00 am
PDX
-
MDW
1 stop8h 14m
Delta
Tue 2/171:49 pm
MDW
-
PDX
1 stop8h 41m
Delta
Deal found 1/20$217
This United Airlines deal was found by Cheapflights users on 1/19. 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.
Wed 2/41:24 pm
PDX
-
ORD
1 stop5h 51m
United Airlines
Wed 2/119:10 am
ORD
-
PDX
Nonstop4h 47m
United Airlines
Deal found 1/19$220
This United Airlines deal was found by Cheapflights users on 1/20. 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.
Sat 5/1611:55 pm
PDX
-
ORD
Nonstop4h 05m
United Airlines
Sat 5/307:35 pm
ORD
-
PDX
Nonstop4h 33m
United Airlines
Deal found 1/20$221
This United Airlines deal was found by Cheapflights users on 1/21. 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.
Wed 2/111:24 pm
PDX
-
ORD
1 stop5h 51m
United Airlines
Sun 2/157:10 am
ORD
-
PDX
1 stop8h 34m
United Airlines
Deal found 1/21$223
This Southwest deal was found by Cheapflights users on 1/21. 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.
Tue 4/1411:55 pm
PDX
-
MDW
Nonstop3h 55m
Southwest
Wed 4/223:40 pm
MDW
-
PDX
1 stop7h 05m
Southwest
Deal found 1/21$223
This United Airlines deal was found by Cheapflights users on 1/21. 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.
Sat 2/75:00 am
PDX
-
ORD
1 stop7h 55m
United Airlines
Wed 2/189:10 am
ORD
-
PDX
Nonstop4h 45m
United Airlines
Deal found 1/21$224
This Southwest deal was found by Cheapflights users on 1/20. 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.
Tue 2/36:20 am
PDX
-
MDW
1 stop8h 25m
Southwest
Tue 2/243:35 pm
MDW
-
PDX
Nonstop4h 25m
Southwest
Deal found 1/20$224
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 2/141:36 pm
PDX
-
ORD
1 stop8h 20m
Hawaiian Airlines
Sat 2/212:07 pm
ORD
-
PDX
Nonstop4h 43m
Hawaiian Airlines
Deal found 1/20$226
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 3/612:04 pm
PDX
-
STL
1 stop19h 45m
Frontier
Mon 3/98:12 pm
STL
-
PDX
2 stops38h 46m
Frontier
Deal found 1/20$226
This Delta deal was found by Cheapflights users on 1/21. 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 2/1912:40 am
PDX
-
ORD
1 stop9h 05m
Delta
Tue 3/38:50 am
ORD
-
PDX
1 stop5h 54m
Delta
Deal found 1/21$227

Find flight deals from Portland to Illinois

Keep the following information in mind while searching for Portland to Illinois flight deals. Data was last updated January 21, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$197
(Kiwi.com)

One-way from

$67
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$302

Good round-trip deal

$300 or less

Good one-way deal

$169 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. 5% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 21, 2026.
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 2/20

1:40 pm-11:26 pm

1 stop7h 46m

Chicago O'Hare Intl

Tue 3/3

12:45 pm-3:27 pm

Nonstop4h 42m

$217

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 2/14

1:27 pm-11:52 pm

1 stop8h 25m

Chicago O'Hare Intl

Sat 2/21

8:50 am-12:44 pm

1 stop5h 54m

$217

PortlandChicago

PDX - MDW

PDXMDW

Portland

Fri 3/13

11:55 pm-5:45 am

Nonstop3h 50m

Chicago Midway

Wed 3/18

8:45 pm-11:10 pm

Nonstop4h 25m

$217

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 2/18

5:30 am-1:22 pm

1 stop5h 52m

Chicago O'Hare Intl

Wed 2/25

6:45 pm-11:53 pm

1 stop7h 08m

$217

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 3/24

11:59 pm-5:53 am

Nonstop3h 54m

Chicago O'Hare Intl

Wed 4/1

6:25 am-12:26 pm

1 stop8h 01m

$217

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sat 2/14

6:00 am-4:14 pm

1 stop8h 14m

Chicago Midway

Tue 2/17

1:49 pm-8:30 pm

1 stop8h 41m

$217

PortlandChicago

PDX - MDW

PDXMDW

Portland

Tue 3/31

12:30 am-8:50 am

1 stop6h 20m

Chicago Midway

Wed 4/8

2:05 pm-8:25 pm

1 stop8h 20m

$217

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 4/21

1:35 pm-11:59 pm

1 stop8h 24m

Chicago O'Hare Intl

Thu 4/30

3:52 pm-11:59 pm

1 stop10h 07m

$227

PortlandChicago

PDX - MDW

PDXMDW

Portland

Sun 2/22

6:45 am-12:40 pm

Nonstop3h 55m

Chicago Midway

Wed 2/25

5:05 am-10:50 am

1 stop7h 45m

$227

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 2/20

11:59 pm-5:53 am

Nonstop3h 54m

Chicago O'Hare Intl

Sun 2/22

6:25 am-12:38 pm

1 stop8h 13m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

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 July is currently the most expensive (average of $237). 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 January 21, 2026.

It’s typically best to fly out from Portland to Illinois in the afternoon. Doing so could potentially save you 20% on the flight price compared to flying in the evening, 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 January 17, 2026.

Travelers seeking maximum savings on their Portland to Illinois flight should consider departing on Wednesday afternoons 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.

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 January 21, 2026.

The most flights from PDX to USIL are scheduled on a Monday (17 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (10 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 January 21, 2026.
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
11,775 reviews

Entertainment

7.0

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Alaska Airlines
8.0
Very good
11,775 reviews
Alaska Airlines
8.0
Very good
11,775 reviews

Entertainment

7.0

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Southwest
8.0
Very good
4,266 reviews
Alaska Airlines
8.0
Very good
11,775 reviews

Entertainment

7.0

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Hawaiian Airlines
7.8
Good
2,829 reviews
Alaska Airlines
8.0
Very good
11,775 reviews

Entertainment

7.0

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
United Airlines
7.4
Good
9,191 reviews
Alaska Airlines
8.0
Very good
11,775 reviews

Entertainment

7.0

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
American Airlines
7.2
Good
11,174 reviews
Alaska Airlines
8.0
Very good
11,775 reviews

Entertainment

7.0

Food

7.1

Crew

8.5

Comfort

7.8

Overall

8.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

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 United Airlines, Delta, and Southwest fly from Portland to Illinois in about 3h 50m. The time it takes to get you to your destination can typically vary by up to 4h 35m. Airlines will cover a distance of 1746 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 Frontier, which is currently one of the cheapest options available, starting at $30. Spirit Airlines flights start at $52 while deals on Hawaiian Airlines start at $52 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%), Qatar Airways (88%), United Airlines (86%).

  • What are the cheapest flights from Portland to Illinois?

    On average you can expect to pay $905 for a flight from Portland to Illinois. The cheapest flight overall is $108 while the most popular route, (Portland - Chicago O'Hare Intl) is currently priced at $193.

  • 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 July is currently the most expensive (average of $237). 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

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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 January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$86Average$243FlexibilityNo cancel feeOn-time62%
DeltaCheapest$99Average$327FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$119Average$184FlexibilityNo cancel feeOn-time65%
Hawaiian AirlinesCheapest$125Average$283FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$196Average$452FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$208Average$451FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$217Average$350FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$237Average$376FlexibilityNo cancel feeOn-time63%

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