HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chesapeake

$166+ 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — RIC
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Portland to Chesapeake with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Portland to Chesapeake are usually found in January or October, booked 88 days in advance, depart on a Thursday or Tuesday and return on a Thursday

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 November 6, 2025.

This Delta deal was found by Cheapflights users on 11/4. 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.
Thu 11/276:10 amPDX - ORF
1 stop9h 24mDelta
Wed 12/312:13 pmORF - PDX
1 stop11h 27mDelta
Deal found 11/4$363
This United Airlines deal was found by Cheapflights users on 11/5. 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.
Wed 12/310:50 amPDX - ORF
1 stop7h 10mUnited Airlines
Wed 12/106:05 amORF - PDX
1 stop8h 43mUnited Airlines
Deal found 11/5$367
This Delta deal was found by Cheapflights users on 11/5. 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 12/37:09 pmPDX - ORF
2 stops11h 00mDelta
Wed 12/105:40 amORF - PDX
2 stops10h 14mDelta
Deal found 11/5$377
This Delta deal was found by Cheapflights users on 11/5. 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.
Mon 12/810:10 pmPDX - ORF
1 stop8h 23mDelta
Tue 12/93:15 pmORF - PDX
1 stop10h 04mDelta
Deal found 11/5$378
This United Airlines deal was found by Cheapflights users on 11/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/41:14 pmPDX - ORF
1 stop6h 45mUnited Airlines
Thu 12/116:05 amORF - PDX
1 stop8h 43mUnited Airlines
Deal found 11/6$389
This Delta deal was found by Cheapflights users on 11/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/411:20 pmPDX - ORF
2 stops11h 49mDelta
Thu 12/115:40 amORF - PDX
2 stops10h 14mDelta
Deal found 11/6$399

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 November 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$367
(United Airlines)

One-way from

$166
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$627
Provider with most accurate pricing for Portland-Norfolk flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Norfolk flights.
Search Deals
From Portland to Chesapeake
Search Deals
One-way flight from Portland to Chesapeake
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 6, 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

Thu 11/27

9:59 am-11:12 pm

2 stops10h 13m

Norfolk

Wed 12/3

5:15 am-10:44 am

1 stop8h 29m

$368

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Sun 12/7

12:32 am-4:57 pm

2 stops13h 25m

Norfolk

Tue 12/9

3:15 pm-10:19 pm

1 stop10h 04m

$383

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Wed 2/4

11:05 pm-11:44 am

1 stop9h 39m

Norfolk

Sun 2/8

4:45 pm-10:32 pm

1 stop8h 47m

$407

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Tue 2/3

12:40 am-2:53 pm

2 stops11h 13m

Norfolk

Sun 2/8

3:36 pm-10:15 pm

1 stop9h 39m

$412

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Thu 1/29

12:40 am-2:53 pm

2 stops11h 13m

Norfolk

Mon 2/2

5:20 am-10:49 am

1 stop8h 29m

$423

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Fri 1/30

6:20 am-8:30 pm

2 stops11h 10m

Norfolk

Mon 2/2

12:30 pm-10:15 pm

2 stops12h 45m

$428

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Fri 12/19

11:02 am-9:01 pm

1 stop6h 59m

Norfolk

Fri 12/26

5:15 pm-10:40 pm

1 stop8h 25m

$447

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Fri 1/9

6:30 am-5:50 pm

2 stops8h 20m

Norfolk

Sun 1/11

11:50 am-8:15 pm

2 stops11h 25m

$457

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Mon 11/24

5:30 am-12:13 am

2 stops15h 43m

Norfolk

Thu 12/4

12:13 pm-8:40 pm

1 stop11h 27m

$463

PortlandNorfolk

PDX - ORF

PDXORF

Portland

Thu 11/20

11:53 am-9:49 pm

1 stop6h 56m

Norfolk

Wed 12/3

12:13 pm-10:10 pm

2 stops12h 57m

$472

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

Showing 1-10 of 19 results
1
2

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 October 31, 2025.

To ensure you get the cheapest price possible for a flight from Portland to Chesapeake, you should look to book at least 88 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, June is the cheapest month in which you can book a flight from Portland to Chesapeake (average of $202). Flying from Portland to Chesapeake in March is currently the most expensive (average of $378). 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 November 6, 2025.

It’s typically best to fly out from Portland to Chesapeake at noon. Doing so could potentially save you 21% on the flight price compared to flying in the afternoon, which is usually more expensive.

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 Saturday afternoons when fares are most often at their lowest. Sunday afternoons 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 November 6, 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

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
8,001 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,007 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,040 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Portland to Chesapeake?

    Delta and United Airlines can get you from Portland to Chesapeake in just under 9h 39m. Your travel time can differ by up to 34m. The distance from Portland to Chesapeake is about 2446 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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, June is the cheapest month in which you can book a flight from Portland to Chesapeake (average of $202). Flying from Portland to Chesapeake in March is currently the most expensive (average of $378). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Portland to Chesapeake

See prices for flight routes from nearby airports that may be better suited for you.
Portland to Reagan-National flights
Portland to Dulles Intl flights
Portland to Raleigh flights
Boise to Dulles Intl flights
Portland to Richmond flights
Eugene to Dulles Intl flights
Portland to Norfolk flights
Boise to Reagan-National flights
Eugene to Reagan-National flights
Redmond to Dulles Intl flights
Portland to Charlottesville flights
Portland to Greensboro flights
Boise to Raleigh flights
Redmond to Reagan-National flights
Medford to Dulles Intl flights
Boise to Richmond flights
Portland to Roanoke flights
Eugene to Raleigh flights
Portland to Blountville flights
Medford to Reagan-National flights
Boise to Norfolk flights
Redmond to Raleigh flights
Eugene to Norfolk flights
Medford to Norfolk flights
Portland to Lynchburg flights
Medford to Richmond flights
Boise to Greensboro flights
Medford to Greensboro flights
Medford to Raleigh flights
Eugene to Richmond flights
Eugene to Greensboro flights
Eugene to Blountville flights
North Bend to Dulles Intl flights
Boise to Charlottesville flights
Boise to Roanoke flights
Redmond to Charlottesville flights
Yakima to Raleigh flights
Portland to Salisbury flights
Redmond to Blountville flights
Yakima to Dulles Intl flights
Portland to Newport News flights
Yakima to Reagan-National flights
Medford to Roanoke flights
Boise to Lynchburg flights
Boise to Newport News flights
Portland to Staunton flights
Medford to Newport News flights
Eugene to Newport News flights
Boise to Staunton flights

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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$278Average$514FlexibilityNo cancel feeOn-time69%
DeltaCheapest$302Average$494FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$332Average$651FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$344Average$514FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.