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Chesapeake

$149+ 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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — RIC
ago. 4 — ago. 111
lun. 8/4
lun. 8/11
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Chesapeake are usually found in January or September, booked 27 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 julio 30, 2025.

Round-trip from

$333
(American Airlines)

One-way from

$149
(Booking.com)

Popular in

December

Cheapest in

January

Average price

$617
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 ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($11 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 julio 30, 2025.

This American Airlines deal was found by Cheapflights users on 7/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/1911:12 pmPDX - ORF
1 stop7h 13mAmerican Airlines
mié. 8/276:21 pmORF - PDX
1 stop7h 59mAmerican Airlines
Deal found 7/27$333
This Delta deal was found by Cheapflights users on 7/27. 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. 8/195:05 pmPDX - ORF
2 stops15h 37mDelta
mar. 8/266:00 amORF - PDX
1 stop7h 40mDelta
Deal found 7/27$338
This Mytrip deal was found by Cheapflights users on 7/28. 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.
jue. 9/188:04 pmPDX - ORF
3 stops17h 39mSpirit Airlines
lun. 9/222:05 pmORF - PDX
3 stops31h 59mSpirit Airlines
Deal found 7/28$364
This United Airlines deal was found by Cheapflights users on 7/28. 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.
jue. 9/1810:06 amPDX - ORF
1 stop10h 25mUnited Airlines
lun. 9/2212:45 pmORF - PDX
1 stop8h 46mUnited Airlines
Deal found 7/28$390
This Mytrip deal was found by Cheapflights users on 7/28. 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.
mar. 8/196:45 pmPDX - ORF
2 stops18h 40mMultiple Airlines
mar. 8/265:20 pmORF - PDX
3 stops28h 37mMultiple Airlines
Deal found 7/28$417
This Southwest deal was found by Cheapflights users on 7/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/189:05 pmPDX - ORF
1 stop11h 20mSouthwest
lun. 9/225:30 amORF - PDX
2 stops11h 25mSouthwest
Deal found 7/28$419

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 julio 30, 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

mar. 8/19

11:12 pm-9:25 am

1 stop7h 13m

Norfolk

mar. 8/26

3:44 pm-10:59 pm

1 stop10h 15m

$333

PortlandNorfolk

PDX - ORF

PDXORF

Portland

mar. 8/19

5:05 pm-11:42 am

2 stops15h 37m

Norfolk

mar. 8/26

6:00 am-10:40 am

1 stop7h 40m

$338

PortlandNorfolk

PDX - ORF

PDXORF

Portland

jue. 9/18

8:04 pm-4:43 pm

3 stops17h 39m

Norfolk

lun. 9/22

2:05 pm-7:04 pm

3 stops31h 59m

$364

PortlandNorfolk

PDX - ORF

PDXORF

Portland

jue. 9/18

10:06 am-11:31 pm

1 stop10h 25m

Norfolk

lun. 9/22

12:45 pm-6:31 pm

1 stop8h 46m

$390

PortlandNorfolk

PDX - ORF

PDXORF

Portland

mar. 8/19

6:45 pm-4:25 pm

2 stops18h 40m

Norfolk

mar. 8/26

5:20 pm-6:57 pm

3 stops28h 37m

$417

PortlandNorfolk

PDX - ORF

PDXORF

Portland

jue. 9/18

9:05 pm-11:25 am

1 stop11h 20m

Norfolk

lun. 9/22

5:30 am-1:55 pm

2 stops11h 25m

$419

PortlandNorfolk

PDX - ORF

PDXORF

Portland

jue. 9/25

12:07 pm-1:10 pm

2 stops22h 03m

$149

PortlandNorfolk

PDX - ORF

PDXORF

Portland

mié. 10/15

10:10 pm-9:00 am

1 stop7h 50m

$167

PortlandNorfolk

PDX - ORF

PDXORF

Portland

mié. 9/17

6:27 pm-9:24 am

2 stops11h 57m

$172

PortlandNorfolk

PDX - ORF

PDXORF

Portland

dom. 8/31

9:05 pm-9:10 am

1 stop9h 05m

$179

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

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 July 25, 2025.

To ensure you get the cheapest price possible for a flight from Portland to Chesapeake, you should look to book at least 27 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 julio 30, 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 julio 30, 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
4,241 reviews

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,896 reviews
Southwest
8.0
Very good
4,241 reviews

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,241 reviews

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Allegiant Air
7.2
Good
703 reviews
Southwest
8.0
Very good
4,241 reviews

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

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

    To fly one-way, consider booking your trip with Spirit 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 $172 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 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 julio 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$323Average$487FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$344Average$692FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$346Average$551FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$387Average$522FlexibilityNo cancel feeOn-time63%

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