$69+ 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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
PIT — RIC
Sep 10 — Sep 171
Round-trip
1 adult, Economy
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Find cheap flights from Pittsburgh 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 Pittsburgh to Chesapeake are usually found in May or November, booked 74 days in advance, depart on a Monday or Wednesday and return on a Friday
Cheap flight deals from Pittsburgh to Chesapeake
Cheapest
Best
Last-minute
One-way
Cheapest flights from Pittsburgh to ChesapeakeExplore 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 August 11, 2026.
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 August 11, 2026.
This Breeze Airways deal was found by Cheapflights users on 8/6. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/219:21 am -
Nonstop1h 19m
Mon 8/2411:25 am -
Nonstop1h 23m
Deal found 8/6![Breeze Airways logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/289:21 am -
Nonstop1h 19m
Mon 8/3111:25 am -
Nonstop1h 23m
Deal found 8/8![Breeze Airways logo]()
$137
This Breeze Airways deal was found by Cheapflights users on 8/8. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/29:23 am -
Nonstop1h 19m
Sun 10/43:49 pm -
1 stop5h 36m
Deal found 8/8![Breeze Airways logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/219:23 am -
Nonstop1h 19m
Mon 9/2811:22 am -
Nonstop1h 23m
Deal found 8/8![Breeze Airways logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/169:23 am -
Nonstop1h 19m
Mon 10/1911:22 am -
Nonstop1h 23m
Deal found 8/9![Breeze Airways logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/219:23 am -
Nonstop1h 19m
Fri 9/2511:22 am -
Nonstop1h 23m
Deal found 8/9![Breeze Airways logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 8/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/234:13 pm -
Nonstop1h 19m
Sun 11/13:49 pm -
1 stop5h 36m
Deal found 8/7![Breeze Airways logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/79:21 am -
Nonstop1h 19m
Mon 9/1411:22 am -
Nonstop1h 23m
Deal found 8/9![Breeze Airways logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/179:21 am -
Nonstop1h 19m
Fri 8/2111:25 am -
Nonstop1h 23m
Deal found 8/8![Breeze Airways logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/119:23 am -
Nonstop1h 19m
Mon 9/147:43 pm -
1 stop18h 04m
Deal found 8/9![Multiple Airlines logo]()
$202
Best flights from Pittsburgh to ChesapeakeDiscover carefully curated flight deals from Pittsburgh to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 11, 2026.
Discover carefully curated flight deals from Pittsburgh to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 11, 2026.
This Delta deal was found by Cheapflights users on 8/10. 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.
Tue 10/207:54 pm -
1 stop4h 51m
Sat 10/246:00 am -
1 stop4h 37m
Deal found 8/10![Delta logo]()
$207
This Southwest deal was found by Cheapflights users on 8/10. 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.
Sat 9/123:30 pm -
1 stop5h 30m
Sat 9/196:25 am -
1 stop5h 45m
Deal found 8/10![Southwest logo]()
$259
This Breeze Airways deal was found by Cheapflights users on 8/9. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/49:21 am -
Nonstop1h 19m
Mon 9/711:25 am -
Nonstop1h 23m
Deal found 8/9![Breeze Airways logo]()
$288
This KAYAK deal was found by Cheapflights users on 8/9. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:56 pm -
1 stop5h 46m
Wed 9/26:23 am -
1 stop5h 22m
Deal found 8/9![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 8/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/175:35 am -
1 stop3h 55m
Mon 9/2810:10 am -
2 stops7h 00m
Deal found 8/6![Southwest logo]()
$284
This Delta deal was found by Cheapflights users on 8/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/48:13 am -
1 stop5h 32m
Sat 11/75:25 pm -
1 stop7h 21m
Deal found 8/7![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 8/7. 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.
Fri 9/42:45 pm -
1 stop7h 15m
Fri 9/113:45 pm -
2 stops7h 30m
Deal found 8/7![Southwest logo]()
$304
This Southwest deal was found by Cheapflights users on 8/7. 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 9/236:30 am -
2 stops8h 00m
Thu 9/243:45 pm -
1 stop6h 10m
Deal found 8/7![Southwest logo]()
$304
This Delta deal was found by Cheapflights users on 8/10. 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 10/912:20 pm -
1 stop4h 04m
Sun 10/116:00 am -
1 stop6h 08m
Deal found 8/10![Delta logo]()
$308
This Southwest deal was found by Cheapflights users on 8/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2012:35 pm -
2 stops9h 30m
Sat 10/246:25 am -
1 stop5h 40m
Deal found 8/6![Southwest logo]()
$304
This Southwest deal was found by Cheapflights users on 8/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/24:20 pm -
2 stops7h 15m
Sun 10/46:20 am -
2 stops6h 35m
Deal found 8/8![Southwest logo]()
$318
Last-minute flights from Pittsburgh to ChesapeakeDiscover last-minute flight deals from Pittsburgh to Chesapeake. Data last updated August 11, 2026 and is based on user searches.
Discover last-minute flight deals from Pittsburgh to Chesapeake. Data last updated August 11, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/149:21 am -
Nonstop1h 19m
Fri 8/2111:25 am -
Nonstop1h 23m
Deal found 8/7![Breeze Airways logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/179:21 am -
Nonstop1h 19m
Fri 8/2111:25 am -
Nonstop1h 23m
Deal found 8/8![Breeze Airways logo]()
$197
This Breeze Airways deal was found by Cheapflights users on 8/6. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/219:21 am -
Nonstop1h 19m
Mon 8/2411:25 am -
Nonstop1h 23m
Deal found 8/6![Breeze Airways logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/289:21 am -
Nonstop1h 19m
Mon 8/3111:25 am -
Nonstop1h 23m
Deal found 8/8![Breeze Airways logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/289:21 am -
Nonstop1h 19m
Mon 8/311:20 pm -
2 stops22h 01m
Deal found 8/8![Multiple Airlines logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/79:21 am -
Nonstop1h 19m
Mon 9/1411:22 am -
Nonstop1h 23m
Deal found 8/9![Breeze Airways logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/119:23 am -
Nonstop1h 19m
Mon 9/147:43 pm -
1 stop18h 04m
Deal found 8/9![Multiple Airlines logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/219:23 am -
Nonstop1h 19m
Mon 9/2811:22 am -
Nonstop1h 23m
Deal found 8/8![Breeze Airways logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/219:23 am -
Nonstop1h 19m
Fri 9/2511:22 am -
Nonstop1h 23m
Deal found 8/9![Breeze Airways logo]()
$172
One-way flights from Pittsburgh to ChesapeakeSearch for one-way flight options from Pittsburgh to Chesapeake. Find affordable one-way fares based on user searches. Data last updated August 11, 2026.
Search for one-way flight options from Pittsburgh to Chesapeake. Find affordable one-way fares based on user searches. Data last updated August 11, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/119:23 am -
Nonstop1h 19m
Deal found 8/8![Breeze Airways logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 8/10. 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.
Mon 8/249:21 am -
Nonstop1h 19m
Deal found 8/10![Breeze Airways logo]()
$89
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1010:26 am -
1 stop9h 38m
Deal found 8/8![Breeze Airways logo]()
$106
This Breeze Airways deal was found by Cheapflights users on 8/7. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/1310:26 am -
1 stop9h 38m
Deal found 8/7![Breeze Airways logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/79:21 am -
Nonstop1h 19m
Deal found 8/8![Breeze Airways logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 8/10. 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.
Fri 8/149:21 am -
Nonstop1h 19m
Deal found 8/10![Breeze Airways logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/92:42 pm -
1 stop28h 06m
Deal found 8/8![Frontier logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/19:11 pm -
1 stop11h 57m
Deal found 8/8![Breeze Airways logo]()
$129
This Delta deal was found by Cheapflights users on 8/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:15 pm -
1 stop6h 18m
Deal found 8/8![Delta logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/237:49 pm -
1 stop15h 30m
Deal found 8/8![Breeze Airways logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/49:21 am -
Nonstop1h 19m
Deal found 8/9![Breeze Airways logo]()
$138
Find flight deals from Pittsburgh to Chesapeake
Keep the following information in mind while searching for Pittsburgh to Chesapeake flight deals. Data was last updated August 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $133 (Breeze Airways) |
One-way from | $69 (Kiwi.com) |
Popular in | February |
Cheapest in | May |
Average price | $258 |
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 August 11, 2026.
Use the filters below to find and compare flights from Pittsburgh to Chesapeake that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PittsburghNorfolk
PIT Pittsburgh - ORF Norfolk
PITORF
Pittsburgh
Tue 10/20
7:54 pm-12:45 am
1 stop4h 51m
Norfolk
Sat 10/24
6:00 am-10:37 am
1 stop4h 37m
$207
PittsburghNorfolk
PIT Pittsburgh - ORF Norfolk
PITORF
Pittsburgh
Sat 9/12
3:30 pm-9:00 pm
1 stop5h 30m
Norfolk
Sat 9/19
6:25 am-12:10 pm
1 stop5h 45m
$259
PittsburghNorfolk
PIT Pittsburgh - ORF Norfolk
PITORF
Pittsburgh
Mon 8/31
5:56 pm-11:42 pm
1 stop5h 46m
Norfolk
Wed 9/2
6:23 am-11:45 am
1 stop5h 22m
$269
PittsburghNorfolk
PIT Pittsburgh - ORF Norfolk
PITORF
Pittsburgh
Thu 9/17
5:35 am-9:30 am
1 stop3h 55m
Norfolk
Mon 9/28
10:10 am-5:10 pm
2 stops7h 00m
$284
Quickest round-trip
PittsburghNorfolk
PIT Pittsburgh - ORF Norfolk
PITORF
Pittsburgh
Fri 9/4
9:21 am-10:40 am
Nonstop1h 19m
Norfolk
Mon 9/7
11:25 am-12:48 pm
Nonstop1h 23m
$288
PittsburghNorfolk
PIT Pittsburgh - ORF Norfolk
PITORF
Pittsburgh
Wed 11/4
8:13 am-1:45 pm
1 stop5h 32m
Norfolk
Sat 11/7
5:25 pm-12:46 am
1 stop7h 21m
$299
PittsburghNorfolk
PIT Pittsburgh - ORF Norfolk
PITORF
Pittsburgh
Fri 9/4
2:45 pm-10:00 pm
1 stop7h 15m
Norfolk
Fri 9/11
3:45 pm-11:15 pm
2 stops7h 30m
$304
PittsburghNorfolk
PIT Pittsburgh - ORF Norfolk
PITORF
Pittsburgh
Wed 9/23
6:30 am-2:30 pm
2 stops8h 00m
Norfolk
Thu 9/24
3:45 pm-9:55 pm
1 stop6h 10m
$304
PittsburghNorfolk
PIT Pittsburgh - ORF Norfolk
PITORF
Pittsburgh
Tue 10/20
12:35 pm-10:05 pm
2 stops9h 30m
Norfolk
Sat 10/24
6:25 am-12:05 pm
1 stop5h 40m
$304
PittsburghNorfolk
PIT Pittsburgh - ORF Norfolk
PITORF
Pittsburgh
Fri 10/9
12:20 pm-4:24 pm
1 stop4h 04m
Norfolk
Sun 10/11
6:00 am-12:08 pm
1 stop6h 08m
$308
Showing 1-10 of 23 resultsSorted by cheapest first
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.
PIT-ORF
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
PIT-C6E
PIT-ORF
What is the cheapest time of day to fly from PIT to C6E?
Find hourly flight availability from Pittsburgh 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 August 11, 2026.
It’s typically best to fly out from Pittsburgh to Chesapeake in the afternoon. Doing so could potentially save you 33% on the flight price compared to flying at noon, which is usually more expensive.
How much does it cost to fly round-trip from Pittsburgh to Chesapeake?
Airfare is below average for this route at the moment.
Pittsburgh to Chesapeake flights typically cost between $210 and $305 in August.The cheapest round-trip price found within the last 5 days was $133 on Breeze Airways (Aug 21-Aug 24).
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 August 11, 2026.
Get a feel of what it's like to fly with Breeze Airways,Southwest, andUnited Airlines 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.
Boarding
8.3
Comfort
8.2
Crew
8.7
Entertainment
6.7
Overall
8.2
Food
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Boarding
8.3
Comfort
8.2
Crew
8.7
Entertainment
6.7
Overall
8.2
Food
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Boarding
8.3
Comfort
8.2
Crew
8.7
Entertainment
6.7
Overall
8.2
Food
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Boarding
8.3
Comfort
8.2
Crew
8.7
Entertainment
6.7
Overall
8.2
Food
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Boarding
8.3
Comfort
8.2
Crew
8.7
Entertainment
6.7
Overall
8.2
Food
6.7
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
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.
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Complete your trip to Chesapeake by adding a car rental and/or hotel reservation to your travel itinerary.
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Pittsburgh and Chesapeake flights
Browse other Pittsburgh and Chesapeake flight options. Last updated on August 11, 2026.
Other flights from Pittsburgh
Browse through other flights departing from Pittsburgh. Flights are based on user searches made on Cheapflights and were last updated on August 11, 2026.
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Pittsburgh to Chesapeake flights
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Top 4 airlines flying from Pittsburgh to Chesapeake
Discover the top 4 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 August 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$132 | Average$212 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$196 | Average$359 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$218 | Average$372 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$229 | Average$416 | FlexibilityNo cancel fee | On-time69% |