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Chesapeake

$101+ 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
Jul 14 — Jul 211
Mon 7/14
Mon 7/21
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 July 9, 2025.

Round-trip from

$201
(Delta)

One-way from

$101
(Delta)

Popular in

July

Cheapest in

January

Average price

$656
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. 9% potential increase in price ($53 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 July 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 July 9, 2025.

This Delta deal was found by Cheapflights users on 7/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2010:05 pmPDX - ORF
1 stop8h 02mDelta
Wed 9/245:30 amORF - PDX
1 stop8h 02mDelta
Deal found 7/9$201
This American Airlines deal was found by Cheapflights users on 7/8. 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 8/511:07 pmPDX - ORF
1 stop7h 18mAmerican Airlines
Tue 8/124:00 pmORF - PDX
1 stop7h 47mAmerican Airlines
Deal found 7/8$203
This Southwest deal was found by Cheapflights users on 7/7. 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.
Wed 8/66:40 amPDX - ORF
2 stops12h 00mSouthwest
Wed 8/136:00 pmORF - PDX
1 stop7h 45mSouthwest
Deal found 7/7$209
This Mytrip deal was found by Cheapflights users on 7/8. 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 9/1812:07 pmPDX - ORF
3 stops21h 37mSpirit Airlines
Mon 9/221:39 pmORF - PDX
3 stops32h 25mSpirit Airlines
Deal found 7/8$313
This Mytrip deal was found by Cheapflights users on 7/6. 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 8/19:22 amPDX - ORF
1 stop8h 40mMultiple Airlines
Mon 8/46:30 pmORF - PDX
2 stops17h 48mMultiple Airlines
Deal found 7/6$338

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 July 9, 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 9/20

10:05 pm-9:07 am

1 stop8h 02m

Norfolk

Wed 9/24

5:30 am-10:32 am

1 stop8h 02m

$201

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Tue 8/5

11:07 pm-9:25 am

1 stop7h 18m

Norfolk

Tue 8/12

4:00 pm-8:47 pm

1 stop7h 47m

$203

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Wed 8/6

6:40 am-9:40 pm

2 stops12h 00m

Norfolk

Wed 8/13

6:00 pm-10:45 pm

1 stop7h 45m

$209

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Thu 9/18

12:07 pm-12:44 pm

3 stops21h 37m

Norfolk

Mon 9/22

1:39 pm-7:04 pm

3 stops32h 25m

$313

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Fri 8/1

9:22 am-9:02 pm

1 stop8h 40m

Norfolk

Mon 8/4

6:30 pm-9:18 am

2 stops17h 48m

$338

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Wed 9/17

11:42 am-12:25 am

1 stop9h 43m

$101

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Thu 8/7

5:34 am-6:44 pm

1 stop10h 10m

$102

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Wed 8/20

6:00 pm-9:10 am

2 stops12h 10m

$107

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Mon 9/8

7:35 pm-9:24 am

2 stops10h 49m

$125

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Thu 10/16

2:35 pm-8:40 am

2 stops15h 05m

$178

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/9

Showing 1-10 of 13 results
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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 27, 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 July 9, 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 July 9, 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
4,253 reviews

Entertainment

7.6

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.6

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,958 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.6

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,843 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.6

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.6

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Allegiant Air
7.2
Good
705 reviews
Southwest
8.0
Very good
4,253 reviews

Entertainment

7.6

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 6 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 $101. American Airlines flights start at $102 while deals on Southwest start at $107 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 6 airlines flying from Portland to Chesapeake

Discover the top 6 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 July 9, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$163Average$278FlexibilityNo cancel feeOn-time65%
Sun Country AirCheapest$180Average$386FlexibilityNo cancel feeOn-time83%
DeltaCheapest$312Average$480FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$346Average$545FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$350Average$695FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$387Average$525FlexibilityNo cancel feeOn-time63%

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