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Chesapeake

$98+ Cheap flights from Pittsburgh (PIT) 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 3/18. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — RIC
feb. 14 — feb. 211
sáb. 2/14
sáb. 2/21
1 adult, Economy
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Cheapflights Tip: The best prices from Pittsburgh to Chesapeake are usually found in September or November, booked 58 days in advance, depart on a Tuesday or Monday and return on a Friday

Cheap flight deals from Pittsburgh to Chesapeake

Keep the following information in mind while searching for Pittsburgh to Chesapeake flight deals. Data was last updated enero 15, 2026.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$177
(Kiwi.com)

One-way from

$98
(Kiwi.com)

Popular in

January

Cheapest in

September

Average price

$534
Provider with most accurate pricing for Pittsburgh-Norfolk flight deals.
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Provider most trusted by Cheapflights users for Pittsburgh-Norfolk flights.
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From Pittsburgh to Chesapeake
Search Deals
One-way flight from Pittsburgh to Chesapeake
Search Deals
Highest demand for flights based on searches. 25% potential increase in price ($101 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($21 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Pittsburgh to Chesapeake

Cheapest flights from Pittsburgh to Chesapeake
Explore the most affordable flight options available from Pittsburgh to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on enero 15, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 1/306:00 am
PIT
-
ORF
1 stop12h 38m
Spirit Airlines
lun. 2/27:33 pm
ORF
-
PIT
1 stop14h 07m
Spirit Airlines
Deal found 1/13$177
This Kiwi.com deal was found by Cheapflights users on 1/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/56:00 am
PIT
-
ORF
1 stop12h 26m
Spirit Airlines
lun. 3/97:31 pm
ORF
-
PIT
1 stop28h 28m
Spirit Airlines
Deal found 1/14$199
This Kiwi.com deal was found by Cheapflights users on 1/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/269:09 pm
PIT
-
ORF
1 stop21h 17m
Multiple Airlines
dom. 3/110:22 am
ORF
-
PIT
1 stop4h 04m
Multiple Airlines
Deal found 1/13$201
This Kiwi.com deal was found by Cheapflights users on 1/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/116:00 am
PIT
-
ORF
2 stops28h 51m
Multiple Airlines
mié. 2/187:31 pm
ORF
-
PIT
1 stop24h 43m
Multiple Airlines
Deal found 1/14$206
This Kiwi.com deal was found by Cheapflights users on 1/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/56:00 am
PIT
-
ORF
1 stop12h 26m
Multiple Airlines
dom. 3/810:22 am
ORF
-
PIT
1 stop4h 04m
Multiple Airlines
Deal found 1/14$222
This Kiwi.com deal was found by Cheapflights users on 1/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 2/116:00 am
PIT
-
ORF
2 stops11h 20m
Spirit Airlines
mié. 2/187:31 pm
ORF
-
PIT
1 stop24h 43m
Spirit Airlines
Deal found 1/14$226
This Kiwi.com deal was found by Cheapflights users on 1/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 2/196:00 am
PIT
-
ORF
1 stop12h 26m
Spirit Airlines
dom. 2/227:31 pm
ORF
-
PIT
1 stop28h 28m
Spirit Airlines
Deal found 1/13$227
This Kiwi.com deal was found by Cheapflights users on 1/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 3/56:00 am
PIT
-
ORF
1 stop12h 26m
Spirit Airlines
mar. 3/107:31 pm
ORF
-
PIT
2 stops21h 08m
Spirit Airlines
Deal found 1/14$230
This Breeze Airways deal was found by Cheapflights users on 1/15. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 7/109:21 am
PIT
-
ORF
Nonstop1h 19m
Breeze Airways
lun. 7/1311:25 am
ORF
-
PIT
Nonstop1h 23m
Breeze Airways
Deal found 1/15$238

Cheapflights Fare Finder

 
Customize your flight search to find flights from Pittsburgh 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 enero 15, 2026.
Use the filters below to find and compare flights from Pittsburgh to Chesapeake that are best for you.

Fly from

Pittsburgh

Fly to

Chesapeake

Route

Depart

Return

Price

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

vie. 1/30

6:00 am-6:38 pm

1 stop12h 38m

Norfolk

lun. 2/2

7:33 pm-9:40 am

1 stop14h 07m

$177

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

jue. 3/5

6:00 am-6:26 pm

1 stop12h 26m

Norfolk

lun. 3/9

7:31 pm-11:59 pm

1 stop28h 28m

$199

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

mié. 2/11

6:00 am-10:51 am

2 stops28h 51m

Norfolk

mié. 2/18

7:31 pm-8:14 pm

1 stop24h 43m

$206

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

jue. 3/5

6:00 am-6:26 pm

1 stop12h 26m

Norfolk

dom. 3/8

10:22 am-2:26 pm

1 stop4h 04m

$222

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

jue. 2/26

9:09 pm-1:46 pm

2 stops16h 37m

Norfolk

dom. 3/1

10:22 am-2:26 pm

1 stop4h 04m

$224

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

jue. 3/5

6:00 am-6:26 pm

1 stop12h 26m

Norfolk

mar. 3/10

7:31 pm-4:39 pm

2 stops21h 08m

$230

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

vie. 7/10

9:21 am-10:40 am

Nonstop1h 19m

Norfolk

lun. 7/13

11:25 am-12:48 pm

Nonstop1h 23m

$238

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

vie. 3/13

6:00 am-7:46 pm

1 stop13h 46m

Norfolk

lun. 3/16

8:41 pm-9:12 pm

1 stop24h 31m

$249

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

vie. 2/27

9:09 pm-7:49 pm

1 stop22h 40m

Norfolk

vie. 3/6

8:20 am-11:25 pm

1 stop15h 05m

$259

PittsburghNorfolk

PIT - ORF

PITORF

Pittsburgh

mié. 3/18

10:45 am-7:46 pm

1 stop9h 01m

$98

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/14

Showing 1-10 of 19 results
1
2

Best time to book a flight from Pittsburgh to Chesapeake

Have a flexible travel schedule? Discover the best time to fly to Chesapeake from Pittsburgh 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 Pittsburgh to Chesapeake

How far ahead should I book a flight from Pittsburgh to Chesapeake?

Use this chart to determine the optimal time to book a round-trip flight from Pittsburgh to Chesapeake. Price data was last updated on January 9, 2026.

The price you pay for your flight from Pittsburgh to Chesapeake may vary depending on when you book. For the best chance of a lower fare, look to book 58 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Pittsburgh to Chesapeake?

Currently, September is the cheapest month in which you can book a flight from Pittsburgh to Chesapeake (average of $97). Flying from Pittsburgh to Chesapeake in January is currently the most expensive (average of $246). 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.

How much does it cost to fly round-trip from Pittsburgh to Chesapeake?

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 enero 15, 2026.
Get a feel of what it's like to fly with Breeze Airways, Southwest, and Delta from Pittsburgh to Chesapeake by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
258 reviews

Entertainment

6.7

Boarding

8.3

Comfort

8.2

Crew

8.7

Overall

8.1

Food

6.7

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Breeze Airways
8.1
Very good
258 reviews
Breeze Airways
8.1
Very good
258 reviews

Entertainment

6.7

Boarding

8.3

Comfort

8.2

Crew

8.7

Overall

8.1

Food

6.7

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Southwest
8.0
Very good
4,258 reviews
Breeze Airways
8.1
Very good
258 reviews

Entertainment

6.7

Boarding

8.3

Comfort

8.2

Crew

8.7

Overall

8.1

Food

6.7

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Delta
7.9
Good
8,052 reviews
Breeze Airways
8.1
Very good
258 reviews

Entertainment

6.7

Boarding

8.3

Comfort

8.2

Crew

8.7

Overall

8.1

Food

6.7

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
United Airlines
7.4
Good
9,164 reviews
Breeze Airways
8.1
Very good
258 reviews

Entertainment

6.7

Boarding

8.3

Comfort

8.2

Crew

8.7

Overall

8.1

Food

6.7

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
American Airlines
7.2
Good
11,136 reviews
Breeze Airways
8.1
Very good
258 reviews

Entertainment

6.7

Boarding

8.3

Comfort

8.2

Crew

8.7

Overall

8.1

Food

6.7

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.

Related info for your journey

Find useful and relevant information for your journey from Pittsburgh 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 Pittsburgh to Chesapeake?

    Pittsburgh (PIT), located 13.5 mi from the city center, is the airport you fly out of when you book flights from Pittsburgh to Chesapeake. 5 airlines have flights from Pittsburgh to Chesapeake on a regular basis. Booking flights from Pittsburgh to Chesapeake should not be difficult; the airport handles an average of 0 outbound flights to Chesapeake per day.

  • How long is the flight from Pittsburgh to Chesapeake?

    Departing from Pittsburgh to Chesapeake will take you 12h 38m. There are 330 mi between Pittsburgh and Chesapeake.

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

    For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $79. Users have also found prices from $81 and $88 on Breeze Airways and Delta, respectively.

  • Can I find deals for flights from Pittsburgh to Chesapeake that include hotel bookings?

    Yes. In addition to deals on Pittsburgh to Chesapeake flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Pittsburgh to Chesapeake?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pittsburgh to Chesapeake.

  • Can I find deals for business class flights from Pittsburgh to Chesapeake?

    Yes. Cheapflights offers flight deals from Pittsburgh 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 Pittsburgh to Chesapeake?

    Currently, September is the cheapest month in which you can book a flight from Pittsburgh to Chesapeake (average of $97). Flying from Pittsburgh to Chesapeake in January is currently the most expensive (average of $246). 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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See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Pittsburgh to Chesapeake

Discover the top 5 airlines that operate flights from Pittsburgh 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 enero 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$94Average$178FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$102Average$249FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$158Average$381FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$176Average$336FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$196Average$303FlexibilityNo cancel feeOn-time71%

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