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Chesapeake

$176+ 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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — RIC
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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The best prices from Portland to Chesapeake are usually found in January or October, booked 12 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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$351
(Delta)

One-way from

$176
(Delta)

Popular in

December

Cheapest in

January

Average price

$592
Provider with most accurate pricing for Portland-Norfolk flight deals.
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Provider most trusted by Cheapflights users for Portland-Norfolk flights.
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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. 1% potential increase in price ($7 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This Orbitz deal was found by Cheapflights users on 2/18. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/17:00 amPDX - ORF
1 stop8h 14mMultiple Airlines
Tue 4/86:13 pmORF - PDX
2 stops17h 09mMultiple Airlines
Deal found 2/18$342
This Southwest deal was found by Cheapflights users on 2/19. 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.
Tue 4/85:20 amPDX - ORF
1 stop8h 10mSouthwest
Wed 4/302:25 pmORF - PDX
1 stop9h 30mSouthwest
Deal found 2/19$351
This Delta deal was found by Cheapflights users on 2/19. 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 4/511:00 pmPDX - ORF
1 stop7h 00mDelta
Wed 4/165:30 amORF - PDX
1 stop8h 53mDelta
Deal found 2/19$354
This Mytrip deal was found by Cheapflights users on 2/19. 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.
Fri 3/77:32 pmPDX - ORF
2 stops21h 02mSpirit Airlines
Sun 3/911:25 amORF - PDX
3 stops29h 13mSpirit Airlines
Deal found 2/19$387
This United Airlines deal was found by Cheapflights users on 2/20. 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.
Fri 3/1411:27 pmPDX - ORF
1 stop7h 15mUnited Airlines
Sat 3/154:53 pmORF - PDX
1 stop8h 46mUnited Airlines
Deal found 2/20$409
This American Airlines deal was found by Cheapflights users on 2/18. 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 5/105:26 amPDX - ORF
2 stops11h 12mAmerican Airlines
Sat 5/177:00 amORF - PDX
1 stop10h 16mAmerican Airlines
Deal found 2/18$412
This Alaska Airlines deal was found by Cheapflights users on 2/18. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/208:00 amPDX - ORF
1 stop7h 29mAlaska Airlines
Sat 8/234:41 pmORF - PDX
2 stops10h 12mAlaska Airlines
Deal found 2/18$632

Find flights from Portland to Chesapeake within your budget

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 February 20, 2025.

Fly from

Portland

Fly to

Chesapeake

Route

Depart

Return

Price

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Tue 4/1

7:00 am-6:14 pm

1 stop8h 14m

Norfolk

Tue 4/8

6:13 pm-8:22 am

2 stops17h 09m

$342

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Tue 4/8

5:20 am-4:30 pm

1 stop8h 10m

Norfolk

Wed 4/30

2:25 pm-8:55 pm

1 stop9h 30m

$351

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Sat 4/5

11:00 pm-9:00 am

1 stop7h 00m

Norfolk

Wed 4/16

5:30 am-11:23 am

1 stop8h 53m

$354

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Fri 3/7

7:32 pm-7:34 pm

2 stops21h 02m

Norfolk

Sun 3/9

11:25 am-1:38 pm

3 stops29h 13m

$387

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Fri 3/14

11:27 pm-9:42 am

1 stop7h 15m

Norfolk

Sat 3/15

4:53 pm-10:39 pm

1 stop8h 46m

$409

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Sat 5/10

5:26 am-7:38 pm

2 stops11h 12m

Norfolk

Sat 5/17

7:00 am-2:16 pm

1 stop10h 16m

$412

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Tue 8/12

5:30 pm-9:30 am

2 stops13h 00m

Norfolk

Tue 8/19

5:55 am-4:28 pm

2 stops13h 33m

$707

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Tue 5/13

10:45 pm-9:03 am

1 stop7h 18m

$176

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Sun 5/4

7:01 pm-11:22 am

2 stops13h 21m

$182

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Fri 5/16

11:41 am-11:02 pm

1 stop8h 21m

$201

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 13 results
1
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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.

Travel insights for flights from Portland to Chesapeake

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

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 February 14, 2025.

To ensure you get the cheapest price possible for a flight from Portland to Chesapeake, you should look to book at least 12 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 June is currently the most expensive (average of $372). 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 February 20, 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.

Rainfall in Chesapeake by month

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

In terms of precipitation, rainfall in Chesapeake ranges from 2.9 - 5.8 inches per month. July is typically the wettest month, when rainfall can reach 5.8 in. November is typically the driest time to visit Chesapeake when rainfall is around 2.9 in.

Temperature in Chesapeake by month

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

If weather is an important factor for your trip to Chesapeake, 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 78.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 42.8 F).

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 February 20, 2025.
Read through reviews of airlines operating flights from Portland to Chesapeake, such as Southwest, Alaska Airlines and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Crew

8.7

Boarding

8.2

Comfort

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 7 airlines. Portland is conveniently located just 6.0 mi from Portland’s city center.

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

    To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $176. Spirit Airlines flights start at $182 while deals on American Airlines start at $201 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 June is currently the most expensive (average of $372). 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 7 airlines flying from Portland to Chesapeake

Discover the top 7 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$173Average$279FlexibilityNo cancel feeOn-time65%
FrontierCheapest$219Average$357FlexibilityNo cancel feeOn-time62%
DeltaCheapest$323Average$507FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$353Average$625FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$358Average$708FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$416Average$546FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$454Average$645FlexibilityNo cancel feeOn-time75%
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