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O'Hare Intl

$152+ Cheap flights from Portland (PDX) to O'Hare Intl (ORD)

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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — ORD
Jun 20 — Jun 271
Sat 6/20
Sat 6/27
1 adult, Economy
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Find cheap flights from Portland to O'Hare Intl with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from Portland to Chicago O'Hare Intl are usually found in February or August, booked 90 days in advance, depart on a Wednesday or Friday and return on a Tuesday

Cheap flight deals from Portland to O'Hare Intl

Cheapest flights from Portland to O'Hare Intl
Explore the most affordable flight options available from Portland to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 21, 2026.

This Frontier deal was found by Cheapflights users on 5/16. 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.
Mon 8/312:26 pm
PDX
-
ORD
1 stop6h 26m
Frontier
Mon 8/107:15 am
ORD
-
PDX
1 stop12h 49m
Frontier
Deal found 5/16$303
This Frontier deal was found by Cheapflights users on 5/16. 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.
Fri 8/76:59 pm
PDX
-
ORD
1 stop8h 29m
Frontier
Mon 8/107:15 am
ORD
-
PDX
1 stop12h 49m
Frontier
Deal found 5/16$304
This United Airlines deal was found by Cheapflights users on 5/18. 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 5/277:00 am
PDX
-
ORD
Nonstop4h 13m
United Airlines
Thu 5/287:55 pm
ORD
-
PDX
Nonstop4h 34m
United Airlines
Deal found 5/18$305
This Orbitz deal was found by Cheapflights users on 5/17. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/15:42 pm
PDX
-
ORD
1 stop10h 35m
Multiple Airlines
Wed 8/57:20 am
ORD
-
PDX
Nonstop4h 25m
Multiple Airlines
Deal found 5/17$307
This American Airlines deal was found by Cheapflights users on 5/18. 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.
Sat 6/2710:59 pm
PDX
-
ORD
Nonstop4h 01m
American Airlines
Fri 7/37:20 pm
ORD
-
PDX
Nonstop4h 30m
American Airlines
Deal found 5/18$309
This United Airlines deal was found by Cheapflights users on 5/20. 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 7/410:40 pm
PDX
-
ORD
Nonstop4h 07m
United Airlines
Sat 7/117:00 am
ORD
-
PDX
Nonstop4h 34m
United Airlines
Deal found 5/20$310
This Orbitz deal was found by Cheapflights users on 5/17. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/316:59 pm
PDX
-
ORD
1 stop8h 29m
Multiple Airlines
Wed 8/57:20 am
ORD
-
PDX
Nonstop4h 25m
Multiple Airlines
Deal found 5/17$313
This United Airlines deal was found by Cheapflights users on 5/17. 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 7/152:25 pm
PDX
-
ORD
Nonstop4h 13m
United Airlines
Sat 7/187:55 pm
ORD
-
PDX
Nonstop4h 35m
United Airlines
Deal found 5/17$315
This Orbitz deal was found by Cheapflights users on 5/16. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2110:59 pm
PDX
-
ORD
Nonstop4h 01m
Multiple Airlines
Fri 7/317:15 am
ORD
-
PDX
1 stop12h 49m
Multiple Airlines
Deal found 5/16$318
This flugladen.de deal was found by Cheapflights users on 5/20. 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 flugladen.de is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/2510:59 pm
PDX
-
ORD
Nonstop4h 01m
Alaska Airlines
Wed 7/295:42 pm
ORD
-
PDX
1 stop7h 48m
Alaska Airlines
Deal found 5/20$319

Find flight deals from Portland to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to O'Hare Intl (ORD). 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 May 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$303
(Frontier)

One-way from

$149
(Frontier)

Popular in

December

Cheapest in

February

Average price

$381

Good round-trip deal

$373 or less

Good one-way deal

$200 or less
Provider with most accurate pricing for Portland-Chicago O'Hare Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Chicago O'Hare Intl flights.
Search Deals
From Portland to Chicago O'Hare Intl
Search Deals
One-way flight from Portland to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Portland to Chicago O'Hare Intl.
Search Deals
Price to beat on a one-way flight from Portland to Chicago O'Hare Intl.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to O'Hare Intl 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 May 21, 2026.
Use the filters below to find and compare flights from Portland to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 6/23

10:40 pm-4:45 am

Nonstop4h 05m

Chicago O'Hare Intl

Tue 6/30

6:59 am-9:33 am

Nonstop4h 34m

$310

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 7/11

11:40 pm-5:45 am

Nonstop4h 05m

Chicago O'Hare Intl

Wed 7/15

6:10 am-12:07 pm

1 stop7h 57m

$325

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 7/31

11:40 pm-5:45 am

Nonstop4h 05m

Chicago O'Hare Intl

Tue 8/4

7:00 am-9:34 am

Nonstop4h 34m

$326

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 6/19

11:40 pm-5:45 am

Nonstop4h 05m

Chicago O'Hare Intl

Wed 6/24

6:45 am-9:10 am

Nonstop4h 25m

$326

PortlandChicago

PDX - ORD

PDXORD

Portland

Wed 8/26

4:07 pm-11:59 pm

1 stop5h 52m

Chicago O'Hare Intl

Fri 8/28

9:00 pm-11:40 pm

Nonstop4h 40m

$336

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 7/28

12:33 am-8:30 am

1 stop5h 57m

Chicago O'Hare Intl

Sun 8/2

6:55 am-11:41 am

1 stop6h 46m

$346

PortlandChicago

PDX - ORD

PDXORD

Portland

Tue 7/28

12:33 am-8:30 am

1 stop5h 57m

Chicago O'Hare Intl

Fri 8/7

7:00 am-11:40 am

1 stop6h 40m

$346
Quickest round-trip

PortlandChicago

PDX - ORD

PDXORD

Portland

Fri 8/7

10:59 pm-5:00 am

Nonstop4h 01m

Chicago O'Hare Intl

Tue 8/11

7:20 am-9:45 am

Nonstop4h 25m

$356

PortlandChicago

PDX - ORD

PDXORD

Portland

Thu 6/18

10:40 pm-4:45 am

Nonstop4h 05m

Chicago O'Hare Intl

Tue 6/23

5:00 am-9:47 am

1 stop6h 47m

$356

PortlandChicago

PDX - ORD

PDXORD

Portland

Sat 6/13

7:00 am-4:56 pm

1 stop7h 56m

Chicago O'Hare Intl

Fri 6/19

5:57 pm-11:18 pm

1 stop7h 21m

$357

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/21

Showing 1-10 of 24 resultsSorted by cheapest first
1
2
3

Compare providers for flights from Portland to O'Hare Intl

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Portland to O'Hare Intl in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Portland-Chicago O'Hare Intl Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Portland-Chicago O'Hare Intl Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Portland-Chicago O'Hare Intl Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Portland to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl 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 Chicago O'Hare Intl Airport

How far ahead should I book a flight from Portland to Chicago O'Hare Intl Airport?

Booking 89 days in advance of your planned departure date is, on average, the best time to get cheap flights from Portland to Chicago O'Hare Intl Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Portland to Chicago O'Hare Intl Airport?

Currently, February is the cheapest month in which you can book a flight from Portland to Chicago O'Hare Intl Airport (average of $257). Flying from Portland to Chicago O'Hare Intl Airport in December is currently the most expensive (average of $404). 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 ORD?

Find hourly flight availability from Portland to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 21, 2026.

When flying from Portland to Chicago O'Hare Intl Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 31% versus a flight in the morning.

What is the cheapest day to fly from Portland to Chicago O'Hare Intl Airport?

Use this chart to determine the cheapest time to fly round-trip from Portland to O'Hare Intl. Price data was last updated on May 16, 2026.

Travelers seeking maximum savings on their Portland to Chicago O'Hare Intl Airport 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.

How much does it cost to fly round-trip from Portland to Chicago O'Hare Intl Airport?

The best insider tips for Portland to Chicago O'Hare Intl Airport flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Portland to Chicago O'Hare Intl Airport trip
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Robert Schrader

Robert Schrader

Expert on Alaska Airlines

One of the web's original travel bloggers, Robert launched his first site Leave Your Daily Hell in 2009. Since then, he's expanded into destination niche sites (one each for Japan, Thailand and Taiwan), in addition to having written for the inflight magazines of Singapore Airlines and Korean Air. Overall, he's visited nearly 100 countries, and flies business as often as possible.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Brandon Schultz

Brandon Schultz

Expert on PDX

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated May 21, 2026.
Get a feel of what it's like to fly with Alaska Airlines,Delta, andHawaiian Airlines from Portland to Chicago O'Hare Intl Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
7.9
Good
12,391 reviews

Boarding

8.1

Crew

8.5

Overall

7.9

Food

7.0

Comfort

7.8

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Eugene,Mar 2026

MFR - SEA

Alaska Airlines is is always good. There where few choices of what to drink, and no food. No blankets, no pillows, and you h ats ok. I just had open heart surgery And i could have used something. But the flight and the crew where exelent. So all is well
Alaska Airlines
7.9
Good
12,391 reviews
Alaska Airlines
7.9
Good
12,391 reviews

Boarding

8.1

Crew

8.5

Overall

7.9

Food

7.0

Comfort

7.8

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Eugene,Mar 2026

MFR - SEA

Alaska Airlines is is always good. There where few choices of what to drink, and no food. No blankets, no pillows, and you h ats ok. I just had open heart surgery And i could have used something. But the flight and the crew where exelent. So all is well
Delta
7.9
Good
8,449 reviews
Alaska Airlines
7.9
Good
12,391 reviews

Boarding

8.1

Crew

8.5

Overall

7.9

Food

7.0

Comfort

7.8

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Eugene,Mar 2026

MFR - SEA

Alaska Airlines is is always good. There where few choices of what to drink, and no food. No blankets, no pillows, and you h ats ok. I just had open heart surgery And i could have used something. But the flight and the crew where exelent. So all is well
Hawaiian Airlines
7.8
Good
2,835 reviews
Alaska Airlines
7.9
Good
12,391 reviews

Boarding

8.1

Crew

8.5

Overall

7.9

Food

7.0

Comfort

7.8

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Eugene,Mar 2026

MFR - SEA

Alaska Airlines is is always good. There where few choices of what to drink, and no food. No blankets, no pillows, and you h ats ok. I just had open heart surgery And i could have used something. But the flight and the crew where exelent. So all is well
United Airlines
7.4
Good
9,745 reviews
Alaska Airlines
7.9
Good
12,391 reviews

Boarding

8.1

Crew

8.5

Overall

7.9

Food

7.0

Comfort

7.8

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Eugene,Mar 2026

MFR - SEA

Alaska Airlines is is always good. There where few choices of what to drink, and no food. No blankets, no pillows, and you h ats ok. I just had open heart surgery And i could have used something. But the flight and the crew where exelent. So all is well
American Airlines
7.1
Good
11,639 reviews
Alaska Airlines
7.9
Good
12,391 reviews

Boarding

8.1

Crew

8.5

Overall

7.9

Food

7.0

Comfort

7.8

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Eugene,Mar 2026

MFR - SEA

Alaska Airlines is is always good. There where few choices of what to drink, and no food. No blankets, no pillows, and you h ats ok. I just had open heart surgery And i could have used something. But the flight and the crew where exelent. So all is well

Related info for your journey

Find useful and relevant information for your journey from Portland to O'Hare Intl. 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 Chicago O'Hare Intl?

    For a flight from Portland to Chicago O'Hare Intl, you will be flying from Portland. Portland (PDX) is just 6.0 mi from the center of the city. Portland is the only Portland airport and it handles 21 outbound flights to Chicago O'Hare Intl per day. 6 airlines have flights to Chicago O'Hare Intl from Portland on a regular basis.

  • How long is the flight from Portland to Chicago O'Hare Intl Airport?

    A quick flight from Portland to Chicago O'Hare Intl Airport can take about 4h 05m. United Airlines provides one of the quickest options available for as low as $310. The distance from Portland to Chicago O'Hare Intl Airport is about 1733 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Portland to Chicago O'Hare Intl Airport round-trip?

    Our cheapest airline available from Portland to Chicago O'Hare Intl Airport is Hawaiian Airlines. Our recent data shows that you can find tickets from as low as $93 on this airline. Additional options worth looking into are Frontier and Delta, starting at $96 and $125 round-trip. Hawaiian Airlines is currently priced 72% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Portland to Chicago O'Hare Intl Airport one-way?

    One-way options have recently been found by users for as low as $72 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $79 and Hawaiian Airlines from $98 one-way.

  • What are the most reliable airlines from Portland to Chicago O'Hare Intl Airport?

    No one likes to see their flight delayed. When booking a flight from Portland to Chicago O'Hare Intl Airport consider choosing Alaska Airlines (92%), Qatar Airways (91%) or United Airlines (87%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Portland to Chicago O'Hare Intl Airport?

    The cheapest flight price from Portland to Chicago O'Hare Intl Airport is $146. On average you can expect to pay $1,016. The most popular route, (Portland - Chicago O'Hare Intl), can usually be booked for $304.

  • Can I find deals for flights from Portland to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on Portland to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to O'Hare Intl?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to O'Hare Intl.

  • Can I find deals for business class flights from Portland to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Portland to O'Hare Intl 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 Chicago O'Hare Intl Airport?

    Currently, February is the cheapest month in which you can book a flight from Portland to Chicago O'Hare Intl Airport (average of $257). Flying from Portland to Chicago O'Hare Intl Airport in December is currently the most expensive (average of $404). 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.

See more FAQs

Traveling to a place near Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Rosemont
Schaumburg
Benton Harbor
Naperville
Delavan
Oakbrook Terrace
Lake Geneva
Gurnee
Downers Grove
Des Plaines
Hoffman Estates
Oak Brook
South Holland
Libertyville
Warrenville
Great Lakes
Arlington Heights
Northbrook
Waukegan
Rockford

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Top 6 airlines flying from Portland to O'Hare Intl

Discover the top 6 airlines that operate flights from Portland to O'Hare Intl. 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 May 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$93Average$249FlexibilityNo cancel feeOn-time85%
FrontierCheapest$96Average$238FlexibilityNo cancel feeOn-time62%
DeltaCheapest$125Average$433FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$171Average$321FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$209Average$337FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$217Average$371FlexibilityNo cancel feeOn-time69%

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