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$96+ 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 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
may. 4 — may. 111
dom. 5/4
dom. 5/11
1 adult, Economy
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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 abril 29, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$227
(American Airlines)

One-way from

$96
(Mytrip)

Popular in

March

Cheapest in

January

Average price

$342

Good round-trip deal

$358 or less

Good one-way deal

$170 or less
Provider with most accurate pricing for Portland-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Portland-Chicago (CHI) flights.
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From Portland to Illinois
Search Deals
One-way flight from Portland to Illinois
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($38 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Portland to Illinois.
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Price to beat on a one-way flight from Portland to Illinois.
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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 abril 29, 2025.

This United Airlines deal was found by Cheapflights users on 4/29. 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.
mié. 6/112:12 pmPDX - STL
1 stop6h 33mUnited Airlines
lun. 6/164:32 pmSTL - PDX
1 stop8h 03mUnited Airlines
Deal found 4/29$227
This CheapOair deal was found by Cheapflights users on 4/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/306:35 amPDX - STL
1 stop25h 34mFrontier
lun. 6/27:24 pmSTL - PDX
1 stop6h 55mFrontier
Deal found 4/29$228
This American Airlines deal was found by Cheapflights users on 4/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/213:24 pmPDX - ORD
Nonstop4h 05mAmerican Airlines
mar. 5/278:00 amORD - PDX
Nonstop4h 24mAmerican Airlines
Deal found 4/28$231
This Gotogate deal was found by Cheapflights users on 4/29. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 5/111:37 pmPDX - ORD
1 stop13h 48mMultiple Airlines
jue. 5/158:14 pmORD - PDX
1 stop21h 28mMultiple Airlines
Deal found 4/29$232
This Alaska Airlines deal was found by Cheapflights users on 4/28. 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.
mar. 5/68:45 pmPDX - ORD
1 stop7h 20mAlaska Airlines
mié. 5/79:00 amORD - PDX
1 stop8h 15mAlaska Airlines
Deal found 4/28$233
This Delta deal was found by Cheapflights users on 4/28. 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.
sáb. 5/311:21 pmPDX - ORD
1 stop8h 38mDelta
vie. 6/137:20 pmORD - PDX
1 stop6h 19mDelta
Deal found 4/28$234
This Kiwi.com deal was found by Cheapflights users on 4/28. 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.
jue. 5/85:40 pmPDX - ORD
1 stop9h 45mSpirit Airlines
vie. 5/1611:50 amORD - PDX
1 stop6h 55mSpirit Airlines
Deal found 4/28$235
This Hawaiian Airlines deal was found by Cheapflights users on 4/29. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 6/41:25 pmPDX - ORD
1 stop6h 58mHawaiian Airlines
sáb. 6/147:00 amORD - PDX
Nonstop4h 25mHawaiian Airlines
Deal found 4/29$237
This Frontier deal was found by Cheapflights users on 4/29. 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.
lun. 5/126:20 amPDX - MDW
1 stop10h 48mFrontier
jue. 5/158:03 pmMDW - PDX
1 stop6h 35mFrontier
Deal found 4/29$238
This United Airlines deal was found by Cheapflights users on 4/28. 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.
vie. 5/94:20 pmPDX - ORD
1 stop6h 09mUnited Airlines
mié. 5/145:05 amORD - PDX
1 stop6h 41mUnited Airlines
Deal found 4/28$239
This Southwest deal was found by Cheapflights users on 4/28. 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.
mar. 6/36:35 pmPDX - MDW
1 stop8h 45mSouthwest
mar. 6/105:25 pmMDW - PDX
1 stop8h 00mSouthwest
Deal found 4/28$246
This Delta deal was found by Cheapflights users on 4/28. 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.
sáb. 8/1610:55 pmPDX - MDW
1 stop7h 45mDelta
sáb. 8/235:50 pmMDW - PDX
1 stop7h 14mDelta
Deal found 4/28$247

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 abril 29, 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

PortlandSt. Louis

PDX - STL

PDXSTL

Portland

mar. 6/3

11:59 pm-8:59 am

1 stop7h 00m

Lambert-St Louis

vie. 6/6

5:29 pm-12:36 am

1 stop9h 07m

$227

PortlandSt. Louis

PDX - STL

PDXSTL

Portland

vie. 5/16

6:20 am-9:59 am

1 stop25h 39m

Lambert-St Louis

sáb. 5/24

7:55 pm-12:17 am

1 stop6h 22m

$231

PortlandChicago

PDX - ORD

PDXORD

Portland

mié. 5/21

3:24 pm-9:29 pm

Nonstop4h 05m

Chicago O'Hare Intl

mar. 5/27

8:00 am-10:24 am

Nonstop4h 24m

$231

PortlandChicago

PDX - ORD

PDXORD

Portland

dom. 5/11

1:37 pm-5:25 am

1 stop13h 48m

Chicago O'Hare Intl

jue. 5/15

8:14 pm-3:42 pm

1 stop21h 28m

$232

PortlandChicago

PDX - ORD

PDXORD

Portland

mié. 7/2

6:39 pm-6:12 am

1 stop9h 33m

Chicago O'Hare Intl

mar. 7/8

11:50 am-5:44 pm

1 stop7h 54m

$233

PortlandChicago

PDX - ORD

PDXORD

Portland

sáb. 5/31

5:30 am-2:10 pm

1 stop6h 40m

Chicago O'Hare Intl

jue. 6/12

7:09 am-12:48 pm

1 stop7h 39m

$234

PortlandChicago

PDX - ORD

PDXORD

Portland

mié. 6/4

1:25 pm-10:23 pm

1 stop6h 58m

Chicago O'Hare Intl

sáb. 6/14

7:00 am-9:25 am

Nonstop4h 25m

$237

PortlandChicago

PDX - MDW

PDXMDW

Portland

lun. 5/12

6:20 am-7:08 pm

1 stop10h 48m

Chicago Midway

jue. 5/15

8:03 pm-12:38 am

1 stop6h 35m

$238

PortlandChicago

PDX - ORD

PDXORD

Portland

vie. 5/9

4:20 pm-12:29 am

1 stop6h 09m

Chicago O'Hare Intl

mié. 5/14

5:05 am-9:46 am

1 stop6h 41m

$239

PortlandChicago

PDX - ORD

PDXORD

Portland

mié. 6/4

7:00 am-1:08 pm

Nonstop4h 08m

Chicago O'Hare Intl

vie. 6/13

7:00 am-9:25 am

Nonstop4h 25m

$242

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

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 $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 abril 29, 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 abril 29, 2025.

The most flights from PDX to USIL are scheduled on a Tuesday (24 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (6 on average).

Rainfall in Illinois by month

Plan your trip to Illinois by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Illinois ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Illinois when rainfall is around 1.7 in.

Temperature in Illinois by month

Plan your trip to Illinois by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Illinois, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 abril 29, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest and Delta from Portland to Illinois. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,961 reviews

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,961 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,295 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,929 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,405 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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.

  • 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 $96. Alaska Airlines flights start at $114 while deals on Southwest start at $114 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 (95%), Brussels Airlines (90%), Lufthansa (82%).

  • What are the cheapest flights from Portland to Illinois?

    On average you can expect to pay $871 for a flight from Portland to Illinois. The cheapest flight overall is $117 while the most popular route, (Portland - Chicago O'Hare Intl) is currently priced at $154.

  • 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.

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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 abril 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$82Average$131FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$260FlexibilityNo cancel feeOn-time62%
DeltaCheapest$123Average$344FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$185Average$340FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$201Average$484FlexibilityNo cancel feeOn-time71%
Hawaiian AirlinesCheapest$202Average$362FlexibilityNo cancel feeOn-time85%
United AirlinesCheapest$214Average$462FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$249Average$441FlexibilityNo cancel feeOn-time63%

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