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Chesapeake

$147+ 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 7/2. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — RIC
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Chesapeake are usually found in January or September, booked 60 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 June 12, 2025.

Round-trip from

$297
(Delta)

One-way from

$147
(Mytrip)

Popular in

July

Cheapest in

January

Average price

$548
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. 8% potential increase in price ($49 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Delta deal was found by Cheapflights users on 6/10. 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.
Wed 9/1712:15 pmPDX - ORF
1 stop7h 40mDelta
Wed 9/245:50 amORF - PDX
1 stop7h 49mDelta
Deal found 6/10$297
This American Airlines deal was found by Cheapflights users on 6/11. 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 8/2511:07 pmPDX - ORF
1 stop7h 18mAmerican Airlines
Sat 8/303:40 pmORF - PDX
1 stop8h 12mAmerican Airlines
Deal found 6/11$315
This Mytrip deal was found by Cheapflights users on 6/10. 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 7/119:22 amPDX - ORF
1 stop8h 40mMultiple Airlines
Fri 7/186:30 pmORF - PDX
2 stops22h 45mMultiple Airlines
Deal found 6/10$367
This Mytrip deal was found by Cheapflights users on 6/11. 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.
Thu 7/1010:23 amPDX - ORF
2 stops28h 12mSpirit Airlines
Thu 7/176:30 pmORF - PDX
2 stops22h 45mSpirit Airlines
Deal found 6/11$369
This United Airlines deal was found by Cheapflights users on 6/10. 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.
Tue 7/810:48 amPDX - ORF
1 stop7h 52mUnited Airlines
Tue 7/155:05 pmORF - PDX
1 stop8h 24mUnited Airlines
Deal found 6/10$389
This Southwest deal was found by Cheapflights users on 6/9. 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 7/19:15 pmPDX - ORF
1 stop9h 15mSouthwest
Tue 7/87:25 pmORF - PDX
1 stop7h 30mSouthwest
Deal found 6/9$413
This Alaska Airlines deal was found by Cheapflights users on 6/10. 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.
Sat 7/127:00 amPDX - ORF
2 stops11h 10mAlaska Airlines
Wed 7/165:46 amORF - PDX
2 stops15h 40mAlaska Airlines
Deal found 6/10$537

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 June 12, 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

Wed 9/17

12:15 pm-10:55 pm

1 stop7h 40m

Norfolk

Wed 9/24

5:50 am-10:39 am

1 stop7h 49m

$297

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Mon 8/25

11:07 pm-9:25 am

1 stop7h 18m

Norfolk

Sat 8/30

3:40 pm-8:52 pm

1 stop8h 12m

$315

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Fri 7/11

9:22 am-9:02 pm

1 stop8h 40m

Norfolk

Fri 7/18

6:30 pm-2:15 pm

2 stops22h 45m

$367

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Thu 7/10

10:23 am-5:35 pm

2 stops28h 12m

Norfolk

Thu 7/17

6:30 pm-2:15 pm

2 stops22h 45m

$369

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Tue 7/8

10:48 am-9:40 pm

1 stop7h 52m

Norfolk

Tue 7/15

5:05 pm-10:29 pm

1 stop8h 24m

$389

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Tue 7/1

9:15 pm-9:30 am

1 stop9h 15m

Norfolk

Tue 7/8

7:25 pm-11:55 pm

1 stop7h 30m

$413

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Sat 7/12

7:00 am-9:10 pm

2 stops11h 10m

Norfolk

Wed 7/16

5:46 am-6:26 pm

2 stops15h 40m

$537

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Wed 7/2

12:12 pm-8:15 am

2 stops17h 03m

$147

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Wed 9/17

10:45 am-10:56 pm

1 stop9h 11m

$149

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Sat 8/30

10:05 pm-10:38 am

1 stop9h 33m

$167

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 15 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.

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 June 9, 2025.

To ensure you get the cheapest price possible for a flight from Portland to Chesapeake, you should look to book at least 60 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 June 12, 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 June 12, 2025.
Read through reviews of airlines operating flights from Portland to Chesapeake, such as Alaska Airlines, Southwest and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Crew

8.5

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
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Crew

8.5

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
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Crew

8.5

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
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Crew

8.5

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
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Allegiant Air
7.3
Good
725 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Crew

8.5

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 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 American Airlines, which is currently one of the cheapest options available, starting at $149. Delta flights start at $167 while deals on United Airlines start at $179 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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Alternative routes for Portland to Chesapeake

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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$163Average$278FlexibilityNo cancel feeOn-time65%
Sun Country AirCheapest$180Average$386FlexibilityNo cancel feeOn-time83%
DeltaCheapest$312Average$479FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$331Average$707FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$346Average$561FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$387Average$528FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$421Average$696FlexibilityNo cancel feeOn-time75%

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