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$94+ Cheap flights from Chesapeake, VA to Pittsburgh (PIT)

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 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — PIT
Aug 2 — Aug 91
Sat 8/2
Sat 8/9
1 adult, Economy
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Cheapflights Tip: The best prices from Chesapeake to Pittsburgh are usually found in September or June, booked 42 days in advance, depart on a Monday or Wednesday and return on a Wednesday

Cheap flight deals from Chesapeake to Pittsburgh

Keep the following information in mind while searching for Chesapeake to Pittsburgh flight deals. Data was last updated July 28, 2025.

Round-trip from

$158
(Breeze Airways)

One-way from

$94
(Breeze Airways)

Popular in

February

Cheapest in

September

Average price

$285
From Chesapeake to Pittsburgh
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One-way flight from Chesapeake to Pittsburgh
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Highest demand for flights based on searches. 8% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 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 Chesapeake to Pittsburgh

Cheapest flights from Chesapeake to Pittsburgh
Explore the most affordable flight options available from Chesapeake to Pittsburgh. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 28, 2025.

This Breeze Airways 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/52:46 pmORF - PIT
Nonstop1h 22mBreeze Airways
Mon 9/84:48 pmPIT - ORF
Nonstop1h 18mBreeze Airways
Deal found 7/28$158
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.
Fri 9/55:38 pmORF - PIT
1 stop15h 52mSpirit Airlines
Mon 9/87:00 amPIT - ORF
1 stop9h 43mSpirit Airlines
Deal found 7/28$169
This Southwest deal was found by Cheapflights users on 7/25. 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.
Thu 9/49:45 amORF - PIT
2 stops8h 35mSouthwest
Sun 9/75:50 amPIT - ORF
1 stop4h 00mSouthwest
Deal found 7/25$213
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.
Thu 9/45:38 pmORF - PIT
1 stop15h 52mMultiple Airlines
Sun 9/74:29 pmPIT - ORF
2 stops24h 14mMultiple Airlines
Deal found 7/28$217
This Delta deal was found by Cheapflights users on 7/26. 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.
Fri 8/86:00 amORF - PIT
1 stop3h 49mDelta
Sun 8/107:33 pmPIT - ORF
1 stop3h 39mDelta
Deal found 7/26$353

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chesapeake to Pittsburgh 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 28, 2025.
Use the filters below to find and compare flights from Chesapeake to Pittsburgh that are best for you.

Fly from

Chesapeake

Fly to

Pittsburgh

Route

Depart

Return

Price

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Fri 9/5

2:46 pm-4:08 pm

Nonstop1h 22m

Pittsburgh

Mon 9/8

4:48 pm-6:06 pm

Nonstop1h 18m

$158

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Fri 9/5

5:38 pm-9:30 am

1 stop15h 52m

Pittsburgh

Mon 9/8

7:00 am-4:43 pm

1 stop9h 43m

$169

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Thu 9/4

9:45 am-6:20 pm

2 stops8h 35m

Pittsburgh

Sun 9/7

5:50 am-9:50 am

1 stop4h 00m

$213

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Thu 9/4

5:38 pm-9:30 am

1 stop15h 52m

Pittsburgh

Sun 9/7

4:29 pm-4:43 pm

2 stops24h 14m

$217

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Fri 8/8

6:00 am-9:49 am

1 stop3h 49m

Pittsburgh

Sun 8/10

7:33 pm-11:12 pm

1 stop3h 39m

$353

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Sun 10/5

2:59 pm-4:21 pm

Nonstop1h 22m

$94

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Sat 10/25

1:47 pm-6:19 pm

1 stop4h 32m

$99

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Tue 8/12

5:50 am-7:16 pm

1 stop13h 26m

$125

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Mon 8/11

7:00 am-11:49 am

1 stop4h 49m

$130

NorfolkPittsburgh

ORF - PIT

ORFPIT

Norfolk

Sat 10/25

11:20 am-7:45 pm

2 stops8h 25m

$169

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 13 results
1
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Best time to book a flight from Chesapeake to Pittsburgh

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

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

Use this chart to determine the optimal time to book a round-trip flight from Chesapeake to Pittsburgh. Price data was last updated on July 25, 2025.

The price you pay for your flight from Chesapeake to Pittsburgh may vary depending on when you book. For the best chance of a lower fare, look to book 42 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 Chesapeake to Pittsburgh?

Currently, August is the cheapest month in which you can book a flight from Chesapeake to Pittsburgh (average of $262). Flying from Chesapeake to Pittsburgh in November is currently the most expensive (average of $333). 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 C6E to PIT?

Find hourly flight availability from Chesapeake to Pittsburgh. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 28, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chesapeake to Pittsburgh as you normally would.

What is the cheapest day to fly from Chesapeake to Pittsburgh?

Use this chart to determine the cheapest time to fly round-trip from Chesapeake to Pittsburgh. Price data was last updated on July 20, 2025.

Travelers seeking maximum savings on their Chesapeake to Pittsburgh flight should consider departing on Thursday mornings when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Pittsburgh

Get insights into the airlines that provide service to Pittsburgh. 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 Pittsburgh. Reviews last updated July 28, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and Breeze Airways from Chesapeake to Pittsburgh 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
4,237 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

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
4,237 reviews
Southwest
8.0
Very good
4,237 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

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
7,970 reviews
Southwest
8.0
Very good
4,237 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

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.
Breeze Airways
8.0
Very good
190 reviews
Southwest
8.0
Very good
4,237 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

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
8,886 reviews
Southwest
8.0
Very good
4,237 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

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
4,237 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

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 Chesapeake to Pittsburgh. 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 into for flights to Pittsburgh from Chesapeake?

    Located just 13.5 mi from the city center, Pittsburgh is the airport most travelers will use when flying to Pittsburgh from Chesapeake. Booking flights from Chesapeake to Pittsburgh (PIT) should be relatively easy as there are 0 daily inbound flights from Chesapeake from 5 different airlines.

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

    $94 is the cheapest one-way deal found within the past few days, from Breeze Airways. You may also be able to find cheap deals on American Airlines and Spirit Airlines, with prices starting from $99 and $125, respectively.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Chesapeake to Pittsburgh (average of $262). Flying from Chesapeake to Pittsburgh in November is currently the most expensive (average of $333). 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

Traveling to a place near Pittsburgh?

Book flights to Pittsburgh if you plan to visit one of these locations
Mars
Steubenville
Monroeville
Washington
Wexford
Belle Vernon

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Top 5 airlines flying from Chesapeake to Pittsburgh

Discover the top 5 airlines that operate flights from Chesapeake to Pittsburgh. 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 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$93Average$205FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$186Average$328FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$216Average$355FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$233Average$380FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$261Average$346FlexibilityNo cancel feeOn-time63%

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