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Chesapeake

$157+ 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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — RIC
may. 4 — may. 111
dom. 5/4
dom. 5/11
1 adult, Economy
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Cheapflights Tip: 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 abril 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$313
(American Airlines)

One-way from

$157
(American Airlines)

Popular in

December

Cheapest in

January

Average price

$478
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. 2% potential increase in price ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in April 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 abril 29, 2025.

This American Airlines deal was found by Cheapflights users on 4/29. 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. 9/177:00 amPDX - ORF
1 stop7h 25mAmerican Airlines
mié. 9/246:59 amORF - PDX
1 stop8h 14mAmerican Airlines
Deal found 4/29$313
This Delta deal was found by Cheapflights users on 4/27. 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. 5/275:40 pmPDX - ORF
2 stops12h 18mDelta
mié. 6/44:20 pmORF - PDX
1 stop9h 55mDelta
Deal found 4/27$318
This United Airlines deal was found by Cheapflights users on 4/28. 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.
mié. 8/1311:20 pmPDX - ORF
1 stop7h 21mUnited Airlines
sáb. 8/165:05 pmORF - PDX
1 stop8h 24mUnited Airlines
Deal found 4/28$332
This Mytrip deal was found by Cheapflights users on 4/29. 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.
mié. 5/145:40 pmPDX - ORF
2 stops17h 36mSpirit Airlines
jue. 5/293:11 pmORF - PDX
2 stops28h 34mSpirit Airlines
Deal found 4/29$357
This Southwest deal was found by Cheapflights users on 4/29. 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.
sáb. 7/199:15 pmPDX - ORF
1 stop9h 55mSouthwest
dom. 7/278:30 pmORF - PDX
1 stop7h 15mSouthwest
Deal found 4/29$433
This Mytrip deal was found by Cheapflights users on 4/28. 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.
sáb. 8/236:35 pmPDX - ORF
3 stops24h 19mMultiple Airlines
mié. 8/277:44 pmORF - PDX
3 stops24h 52mMultiple Airlines
Deal found 4/28$630

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 abril 29, 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

mié. 9/17

7:00 am-5:25 pm

1 stop7h 25m

Norfolk

mié. 9/24

6:59 am-12:13 pm

1 stop8h 14m

$313

PortlandNorfolk

PDX - ORF

PDXORF

Portland

mar. 5/27

7:05 pm-8:58 am

2 stops10h 53m

Norfolk

mar. 6/3

4:20 pm-11:15 pm

1 stop9h 55m

$318

PortlandNorfolk

PDX - ORF

PDXORF

Portland

mié. 8/13

11:20 pm-9:41 am

1 stop7h 21m

Norfolk

sáb. 8/16

5:05 pm-10:29 pm

1 stop8h 24m

$332

PortlandNorfolk

PDX - ORF

PDXORF

Portland

mié. 5/14

5:40 pm-2:16 pm

2 stops17h 36m

Norfolk

jue. 5/29

3:11 pm-4:45 pm

2 stops28h 34m

$357

PortlandNorfolk

PDX - ORF

PDXORF

Portland

sáb. 7/19

9:15 pm-10:10 am

1 stop9h 55m

Norfolk

dom. 7/27

8:30 pm-12:45 am

1 stop7h 15m

$433

PortlandNorfolk

PDX - ORF

PDXORF

Portland

sáb. 8/23

6:35 pm-9:54 pm

3 stops24h 19m

Norfolk

mié. 8/27

7:44 pm-5:36 pm

3 stops24h 52m

$630

PortlandNorfolk

PDX - ORF

PDXORF

Portland

lun. 6/30

9:50 pm-10:55 pm

2 stops22h 05m

Norfolk

dom. 7/6

6:00 am-4:25 pm

2 stops13h 25m

$743

PortlandNorfolk

PDX - ORF

PDXORF

Portland

mié. 9/17

12:06 pm-10:32 pm

1 stop7h 26m

$157

PortlandNorfolk

PDX - ORF

PDXORF

Portland

mié. 7/9

11:11 pm-12:44 pm

2 stops10h 33m

$162

PortlandNorfolk

PDX - ORF

PDXORF

Portland

sáb. 8/23

10:51 am-9:52 pm

1 stop8h 01m

$176

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 12 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 April 25, 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 $367). 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 abril 29, 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 abril 29, 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
9,961 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

Food

7.1

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
9,961 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

Food

7.1

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
4,295 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

Food

7.1

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
7,929 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

Food

7.1

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
8,696 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

Food

7.1

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 8 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 $157. Delta flights start at $162 while deals on United Airlines start at $176 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 $367). 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 8 airlines flying from Portland to Chesapeake

Discover the top 8 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 abril 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$163Average$255FlexibilityNo cancel feeOn-time65%
Sun Country AirCheapest$180Average$460FlexibilityNo cancel feeOn-time83%
FrontierCheapest$235Average$354FlexibilityNo cancel feeOn-time62%
DeltaCheapest$312Average$491FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$346Average$692FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$346Average$596FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$387Average$530FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$421Average$696FlexibilityNo cancel feeOn-time75%

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