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Illinois

$68+ 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 1/16. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
ene. 26 — feb. 21
lun. 1/26
lun. 2/2
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 diciembre 27, 2025.

This Frontier deal was found by Cheapflights users on 12/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/3012:47 pmPDX - ORD
1 stop9h 25mFrontier
jue. 1/810:32 pmORD - PDX
1 stop13h 02mFrontier
Deal found 12/24$332
This Alaska Airlines deal was found by Cheapflights users on 12/24. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/311:51 pmPDX - ORD
1 stop8h 08mAlaska Airlines
vie. 1/92:06 pmORD - PDX
Nonstop4h 42mAlaska Airlines
Deal found 12/24$333
This Alaska Airlines deal was found by Cheapflights users on 12/24. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/317:00 amPDX - ORD
Nonstop4h 09mAlaska Airlines
mié. 1/78:00 amORD - PDX
1 stop7h 48mAlaska Airlines
Deal found 12/24$352
This Priceline deal was found by Cheapflights users on 12/25. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/3012:47 pmPDX - ORD
1 stop9h 25mFrontier
lun. 1/51:32 pmORD - PDX
1 stop8h 18mFrontier
Deal found 12/25$403
This Alaska Airlines deal was found by Cheapflights users on 12/24. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/313:59 pmPDX - ORD
1 stop6h 00mAlaska Airlines
sáb. 1/37:00 amORD - PDX
Nonstop4h 50mAlaska Airlines
Deal found 12/24$423
This Alaska Airlines deal was found by Cheapflights users on 12/24. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/317:00 amPDX - ORD
Nonstop4h 09mAlaska Airlines
lun. 1/57:00 amORD - PDX
Nonstop4h 50mAlaska Airlines
Deal found 12/24$432
This Kiwi.com deal was found by Cheapflights users on 12/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/313:59 pmPDX - ORD
1 stop26h 24mMultiple Airlines
mié. 1/74:38 pmORD - PDX
2 stops20h 37mMultiple Airlines
Deal found 12/25$449
This Delta deal was found by Cheapflights users on 12/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/315:30 amPDX - ORD
1 stop5h 50mDelta
dom. 1/47:25 amORD - PDX
1 stop7h 35mDelta
Deal found 12/24$473
This Frontier deal was found by Cheapflights users on 12/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/3012:47 pmPDX - ORD
1 stop9h 25mFrontier
dom. 1/47:00 amORD - PDX
1 stop6h 43mFrontier
Deal found 12/25$492
This Frontier deal was found by Cheapflights users on 12/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/2712:37 pmPDX - ORD
1 stop9h 35mFrontier
mar. 12/307:00 amORD - PDX
1 stop6h 43mFrontier
Deal found 12/25$502
This Delta deal was found by Cheapflights users on 12/25. 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.
lun. 12/295:30 amPDX - STL
1 stop5h 53mDelta
vie. 1/23:43 pmSTL - PDX
1 stop6h 51mDelta
Deal found 12/25$548
This United Airlines deal was found by Cheapflights users on 12/27. 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.
dom. 12/285:00 amPDX - STL
2 stops9h 27mUnited Airlines
dom. 1/410:30 amSTL - PDX
1 stop11h 13mUnited Airlines
Deal found 12/27$553

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 diciembre 27, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$193
(Kiwi.com)

One-way from

$68
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$420

Good round-trip deal

$325 or less

Good one-way deal

$148 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. 6% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 diciembre 27, 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

mar. 1/20

3:45 pm-11:59 pm

1 stop6h 14m

Chicago O'Hare Intl

mar. 1/27

9:10 am-11:57 am

Nonstop4h 47m

$227

PortlandChicago

PDX - ORD

PDXORD

Portland

sáb. 2/14

7:00 am-1:11 pm

Nonstop4h 11m

Chicago O'Hare Intl

mar. 2/17

5:29 pm-11:44 pm

1 stop8h 15m

$227

PortlandSt. Louis

PDX - STL

PDXSTL

Portland

jue. 5/28

11:18 am-5:06 pm

Nonstop3h 48m

Lambert-St Louis

lun. 6/1

6:20 pm-8:37 pm

Nonstop4h 17m

$229

PortlandChicago

PDX - MDW

PDXMDW

Portland

mié. 2/18

6:30 am-12:25 pm

Nonstop3h 55m

Chicago Midway

mié. 2/25

8:10 am-3:40 pm

2 stops9h 30m

$232

PortlandChicago

PDX - ORD

PDXORD

Portland

sáb. 2/14

1:18 pm-9:29 pm

1 stop6h 11m

Chicago O'Hare Intl

sáb. 2/21

6:25 am-12:38 pm

1 stop8h 13m

$232

PortlandChicago

PDX - ORD

PDXORD

Portland

sáb. 1/24

1:24 pm-9:15 pm

1 stop5h 51m

Chicago O'Hare Intl

sáb. 1/31

6:47 am-12:33 pm

1 stop7h 46m

$232

PortlandChicago

PDX - ORD

PDXORD

Portland

mar. 3/10

8:30 am-4:33 pm

1 stop6h 03m

Chicago O'Hare Intl

mar. 3/17

3:54 pm-10:41 pm

1 stop8h 47m

$236

PortlandChicago

PDX - ORD

PDXORD

Portland

sáb. 2/14

1:36 pm-11:56 pm

1 stop8h 20m

Chicago O'Hare Intl

mié. 2/18

5:29 pm-10:41 pm

1 stop7h 12m

$236

PortlandChicago

PDX - ORD

PDXORD

Portland

sáb. 1/17

1:53 pm-9:43 pm

1 stop5h 50m

Chicago O'Hare Intl

dom. 1/18

7:20 am-12:32 pm

1 stop7h 12m

$237

PortlandChicago

PDX - ORD

PDXORD

Portland

sáb. 1/17

11:44 am-11:59 pm

1 stop10h 15m

Chicago O'Hare Intl

mar. 1/20

8:50 am-12:46 pm

1 stop5h 56m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/25

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 $243). 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 diciembre 27, 2025.

It’s typically best to fly out from Portland to Illinois in the afternoon. Doing so could potentially save you 27% 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 December 27, 2025.

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 diciembre 27, 2025.

The most flights from PDX to USIL are scheduled on a Thursday (20 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (13 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 diciembre 27, 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
11,548 reviews

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.
Alaska Airlines
8.0
Very good
11,548 reviews
Alaska Airlines
8.0
Very good
11,548 reviews

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.
Southwest
8.0
Very good
4,256 reviews
Alaska Airlines
8.0
Very good
11,548 reviews

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.
Hawaiian Airlines
7.8
Good
2,819 reviews
Alaska Airlines
8.0
Very good
11,548 reviews

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.
United Airlines
7.4
Good
9,116 reviews
Alaska Airlines
8.0
Very good
11,548 reviews

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.
American Airlines
7.2
Good
11,069 reviews
Alaska Airlines
8.0
Very good
11,548 reviews

Crew

8.5

Food

7.1

Comfort

7.8

Entertainment

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Georgana,Dec 2025

ORD - PDX

Very cordial grew. Thank you. However, crying baby issues and no ear plugs available.

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 Frontier, United Airlines, and Southwest fly from Portland to Illinois in about 3h 55m. The time it takes to get you to your destination can typically vary by up to 3h 43m. 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: SWISS (89%), Air Canada (87%), Gulf Air (87%).

  • What are the cheapest flights from Portland to Illinois?

    On average you can expect to pay $956 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 $217.

  • 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 $243). 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 diciembre 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$96Average$243FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$119Average$184FlexibilityNo cancel feeOn-time65%
DeltaCheapest$123Average$333FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$125Average$286FlexibilityNo cancel feeOn-time85%
American AirlinesCheapest$196Average$456FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$217Average$351FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$222Average$458FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$238Average$377FlexibilityNo cancel feeOn-time63%

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