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$61+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
feb. 11 — feb. 181
mar. 2/11
mar. 2/18
1 adult, Economy
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Cheap flight deals from Portland to Illinois

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to Illinois (USIL). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated febrero 6, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$120
(CheapOair)

One-way from

$65
(Trip.com)

Popular in

March

Cheapest in

February

Average price

$297

Good round-trip deal

$365 or less

Good one-way deal

$209 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
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One-way flight from Portland to Illinois
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($9 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in February 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 febrero 6, 2025.

This CheapOair deal was found by Cheapflights users on 2/5. 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.
lun. 2/249:18 pmPDX - STL
1 stop18h 18mFrontier
mié. 2/266:43 pmSTL - PDX
1 stop15h 57mFrontier
Deal found 2/5$120
This Expedia deal was found by Cheapflights users on 2/5. 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.
mié. 4/302:30 pmPDX - STL
1 stop7h 29mMultiple Airlines
lun. 5/56:53 pmSTL - PDX
1 stop7h 45mMultiple Airlines
Deal found 2/5$214
This Expedia deal was found by Cheapflights users on 2/5. 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.
mié. 4/23:13 pmPDX - ORD
1 stop7h 50mMultiple Airlines
vie. 4/43:16 pmORD - PDX
Nonstop4h 34mMultiple Airlines
Deal found 2/5$225
This CheapOair deal was found by Cheapflights users on 2/5. 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.
mar. 2/115:30 pmPDX - ORD
1 stop10h 37mSpirit Airlines
mar. 2/181:32 pmORD - PDX
1 stop21h 49mSpirit Airlines
Deal found 2/5$226
This Alaska Airlines deal was found by Cheapflights users on 2/5. 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. 10/2111:00 pmPDX - ORD
Nonstop4h 04mAlaska Airlines
mar. 10/282:05 pmORD - PDX
Nonstop4h 34mAlaska Airlines
Deal found 2/5$227
This American Airlines deal was found by Cheapflights users on 2/6. 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. 4/211:59 pmPDX - STL
1 stop6h 49mAmerican Airlines
mar. 4/83:47 pmSTL - PDX
1 stop9h 15mAmerican Airlines
Deal found 2/6$227
This Mytrip deal was found by Cheapflights users on 2/5. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/612:03 pmPDX - MDW
1 stop10h 14mFrontier
lun. 3/106:40 amMDW - PDX
1 stop19h 57mFrontier
Deal found 2/5$229
This Frontier deal was found by Cheapflights users on 2/5. 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. 2/249:00 amPDX - ORD
1 stop14h 01mFrontier
sáb. 3/157:59 pmORD - PDX
1 stop14h 41mFrontier
Deal found 2/5$235
This Delta deal was found by Cheapflights users on 2/5. 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.
mar. 10/211:38 pmPDX - ORD
1 stop8h 06mDelta
sáb. 10/251:55 pmORD - PDX
1 stop6h 13mDelta
Deal found 2/5$247
This Southwest deal was found by Cheapflights users on 2/5. 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.
jue. 2/276:35 amPDX - MDW
Nonstop3h 55mSouthwest
mar. 3/48:30 amMDW - PDX
Nonstop4h 25mSouthwest
Deal found 2/5$247
This Delta deal was found by Cheapflights users on 2/5. 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.
mar. 3/412:59 amPDX - MDW
1 stop6h 36mDelta
mié. 3/1210:25 amMDW - PDX
1 stop9h 07mDelta
Deal found 2/5$252
This Delta deal was found by Cheapflights users on 2/5. 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.
vie. 9/2610:55 pmPDX - STL
1 stop8h 34mDelta
mar. 9/302:15 pmSTL - PDX
1 stop5h 53mDelta
Deal found 2/5$253

Find flights from Portland to Illinois within your budget

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 febrero 6, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PortlandSt. Louis

PDX - STL

PDXSTL

Portland

lun. 2/24

9:18 pm-5:36 pm

1 stop18h 18m

Lambert-St Louis

mié. 2/26

6:43 pm-8:40 am

1 stop15h 57m

$120

PortlandSt. Louis

PDX - STL

PDXSTL

Portland

mié. 4/30

2:30 pm-11:59 pm

1 stop7h 29m

Lambert-St Louis

lun. 5/5

6:53 pm-12:38 am

1 stop7h 45m

$214

PortlandChicago

PDX - ORD

PDXORD

Portland

mié. 4/2

3:13 pm-1:03 am

1 stop7h 50m

Chicago O'Hare Intl

vie. 4/4

3:16 pm-5:50 pm

Nonstop4h 34m

$225

PortlandChicago

PDX - ORD

PDXORD

Portland

lun. 3/17

7:32 pm-12:59 am

2 stops27h 27m

Chicago O'Hare Intl

mar. 4/1

9:57 pm-5:18 pm

3 stops21h 21m

$226

PortlandChicago

PDX - ORD

PDXORD

Portland

mié. 4/23

11:52 pm-5:57 am

Nonstop4h 05m

Chicago O'Hare Intl

mar. 4/29

8:20 pm-11:02 pm

Nonstop4h 42m

$227

PortlandSt. Louis

PDX - STL

PDXSTL

Portland

jue. 3/13

5:26 pm-12:32 am

1 stop5h 06m

Lambert-St Louis

lun. 3/17

7:30 pm-11:44 pm

1 stop6h 14m

$227

PortlandChicago

PDX - ORD

PDXORD

Portland

mié. 3/19

10:06 am-12:44 am

1 stop12h 38m

Chicago O'Hare Intl

mar. 3/25

6:45 am-12:37 am

1 stop19h 52m

$228

PortlandChicago

PDX - ORD

PDXORD

Portland

mié. 2/26

7:00 am-1:04 pm

Nonstop4h 04m

Chicago O'Hare Intl

mar. 3/11

4:05 pm-6:44 pm

Nonstop4h 39m

$232

PortlandChicago

PDX - MDW

PDXMDW

Portland

mié. 5/28

6:20 am-12:27 am

1 stop16h 07m

Chicago Midway

mié. 6/4

6:15 am-12:40 am

1 stop20h 25m

$234

PortlandChicago

PDX - MDW

PDXMDW

Portland

jue. 2/27

6:35 am-12:30 pm

Nonstop3h 55m

Chicago Midway

mar. 3/4

8:30 am-10:55 am

Nonstop4h 25m

$247

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/6

Showing 1-10 of 59 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.

Travel insights for flights from Portland to Illinois

Get recent, data-driven insights about flights from Portland to Illinois including ideal travel times, pricing trends, and more.

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 $323). 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 febrero 6, 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 febrero 6, 2025.

The most flights from PDX to USIL are scheduled on a Thursday (15 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 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 febrero 6, 2025.
Read reviews from past customers who have flown Southwest, Alaska Airlines 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.
Southwest
8.1
Very good
4,549 reviews

Food

7.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,549 reviews
Southwest
8.1
Very good
4,549 reviews

Food

7.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,696 reviews
Southwest
8.1
Very good
4,549 reviews

Food

7.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,388 reviews
Southwest
8.1
Very good
4,549 reviews

Food

7.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,879 reviews
Southwest
8.1
Very good
4,549 reviews

Food

7.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Allegiant Air
7.3
Good
782 reviews
Southwest
8.1
Very good
4,549 reviews

Food

7.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $65. Spirit Airlines flights start at $87 while deals on Alaska Airlines start at $113 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 (97%), SWISS (97%), Lufthansa (95%).

  • What are the cheapest flights from Portland to Illinois?

    On average you can expect to pay $976 for a flight from Portland to Illinois. The cheapest flight overall is $131 while the most popular route, (Portland - Chicago O'Hare Intl) is currently priced at $130.

  • 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 $323). 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 7 airlines flying from Portland to Illinois

Discover the top 7 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 febrero 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$82Average$135FlexibilityNo cancel feeOn-time65%
FrontierCheapest$108Average$242FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$180Average$342FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$189Average$516FlexibilityNo cancel feeOn-time71%
DeltaCheapest$207Average$378FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$217Average$466FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$246Average$392FlexibilityNo cancel feeOn-time63%
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