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Chesapeake

$141+ Cheap flights from Portland (PDX) to Chesapeake, VA

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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — RIC
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Chesapeake are usually found in January or September, booked 88 days in advance, depart on a Thursday or Tuesday and return on a Thursday

Cheap flight deals from Portland to Chesapeake

Keep the following information in mind while searching for Portland to Chesapeake flight deals. Data was last updated September 15, 2025.

Round-trip from

$249
(Delta)

One-way from

$141
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$422
From Portland to Chesapeake
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One-way flight from Portland to Chesapeake
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Highest demand for flights based on searches. 6% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Portland to Chesapeake

Cheapest flights from Portland to Chesapeake
Explore the most affordable flight options available from Portland to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Delta deal was found by Cheapflights users on 9/13. 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 10/41:48 pmPDX - ORF
1 stop7h 37mDelta
Tue 10/145:24 amORF - PDX
1 stop7h 52mDelta
Deal found 9/13$249
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Tue 10/1411:58 pmPDX - ORF
1 stop9h 25mAmerican Airlines
Tue 10/216:13 pmORF - PDX
1 stop7h 53mAmerican Airlines
Deal found 9/15$337
This United Airlines deal was found by Cheapflights users on 9/15. 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 12/51:14 pmPDX - ORF
1 stop6h 45mUnited Airlines
Mon 12/84:45 pmORF - PDX
1 stop8h 30mUnited Airlines
Deal found 9/15$374
This American Airlines deal was found by Cheapflights users on 9/13. 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 10/49:00 amPDX - ORF
2 stops11h 04mAmerican Airlines
Tue 10/142:10 pmORF - PDX
2 stops12h 19mAmerican Airlines
Deal found 9/13$378
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Fri 12/511:59 pmPDX - ORF
2 stops11h 43mAmerican Airlines
Mon 12/82:35 pmORF - PDX
1 stop8h 42mAmerican Airlines
Deal found 9/15$379
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Mon 10/611:59 pmPDX - ORF
1 stop11h 55mAmerican Airlines
Wed 10/83:44 pmORF - PDX
1 stop10h 45mAmerican Airlines
Deal found 9/15$381
This Delta deal was found by Cheapflights users on 9/13. 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 10/41:48 pmPDX - ORF
1 stop7h 37mDelta
Sun 10/125:24 amORF - PDX
1 stop7h 52mDelta
Deal found 9/13$383
This Southwest deal was found by Cheapflights users on 9/15. 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.
Fri 12/56:05 amPDX - ORF
2 stops8h 30mSouthwest
Mon 12/812:15 pmORF - PDX
2 stops12h 45mSouthwest
Deal found 9/15$384
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/47:15 amPDX - ORF
2 stops25h 04mMultiple Airlines
Sun 10/129:32 amORF - PDX
1 stop27h 07mMultiple Airlines
Deal found 9/13$385

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Chesapeake 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 September 15, 2025.
Use the filters below to find and compare flights from Portland to Chesapeake that are best for you.

Fly from

Portland

Fly to

Chesapeake

Route

Depart

Return

Price

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Sat 10/4

1:48 pm-12:25 am

1 stop7h 37m

Norfolk

Tue 10/14

5:24 am-10:16 am

1 stop7h 52m

$249

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Tue 10/14

11:58 pm-12:23 pm

1 stop9h 25m

Norfolk

Tue 10/21

2:10 pm-11:29 pm

2 stops12h 19m

$342

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Sat 11/1

7:12 am-6:06 pm

1 stop7h 54m

Norfolk

Fri 11/7

4:23 pm-10:08 pm

1 stop8h 45m

$383

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Tue 10/7

6:00 am-5:12 pm

1 stop8h 12m

Norfolk

Fri 11/7

4:23 pm-10:08 pm

1 stop8h 45m

$383

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Sat 10/4

1:48 pm-12:25 am

1 stop7h 37m

Norfolk

Sun 10/12

5:24 am-10:16 am

1 stop7h 52m

$383

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Fri 12/5

6:05 am-5:35 pm

2 stops8h 30m

Norfolk

Mon 12/8

12:15 pm-10:00 pm

2 stops12h 45m

$384

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Tue 10/28

12:40 am-3:18 pm

2 stops11h 38m

Norfolk

Sun 11/2

5:45 am-10:29 am

1 stop7h 44m

$388

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Tue 10/21

12:43 pm-9:02 am

2 stops41h 19m

$141

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Tue 10/21

1:23 pm-11:38 pm

1 stop7h 15m

$169

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Mon 10/20

12:40 am-4:22 pm

2 stops12h 42m

$174

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 19 results
1
2

Best time to book a flight from Portland to Chesapeake

Have a flexible travel schedule? Discover the best time to fly to Chesapeake 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 Chesapeake

How far ahead should I book a flight from Portland to Chesapeake?

Use this chart to determine the optimal time to book a round-trip flight from Portland to Chesapeake. Price data was last updated on September 12, 2025.

To ensure you get the cheapest price possible for a flight from Portland to Chesapeake, you should look to book at least 88 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Portland to Chesapeake?

Currently, January is the cheapest month in which you can book a flight from Portland to Chesapeake (average of $281). Flying from Portland to Chesapeake in March is currently the most expensive (average of $351). 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 C6E?

Find hourly flight availability from Portland to Chesapeake. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

When flying from Portland to Chesapeake, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Portland to Chesapeake?

Use this chart to determine the cheapest time to fly round-trip from Portland to Chesapeake. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Portland to Chesapeake flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Chesapeake

Get insights into the airlines that provide service to Chesapeake. 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 Chesapeake. Reviews last updated September 15, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Portland to Chesapeake to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,954 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,929 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Portland to Chesapeake. 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 Chesapeake?

    Most people fly from Portland (PDX) if they book a flight from Portland to Chesapeake. On average, Portland has 0 outbound flights to Chesapeake per day from 4 airlines. Portland is conveniently located just 6.0 mi from Portland’s city center.

  • How long is the flight from Portland to Chesapeake?

    Delta and American Airlines can get you from Portland to Chesapeake in just under 7h 37m. Your travel time can differ by up to 1h 48m. The distance from Portland to Chesapeake is about 2446 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Portland to Chesapeake one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $141. American Airlines flights start at $169 while deals on Delta start at $174 one-way.

  • Can I find deals for flights from Portland to Chesapeake that include hotel bookings?

    Yes. In addition to deals on Portland to Chesapeake flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Chesapeake?

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

  • Can I find deals for business class flights from Portland to Chesapeake?

    Yes. Cheapflights offers flight deals from Portland to Chesapeake 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 Chesapeake?

    Currently, January is the cheapest month in which you can book a flight from Portland to Chesapeake (average of $281). Flying from Portland to Chesapeake in March is currently the most expensive (average of $351). 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

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Top 4 airlines flying from Portland to Chesapeake

Discover the top 4 airlines that operate flights from Portland to Chesapeake. 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$323Average$490FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$332Average$650FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$334Average$513FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$387Average$522FlexibilityNo cancel feeOn-time63%

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