$85+ Cheap flights from Houston 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 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — RIC
Sep 28 — Oct 51
Round-trip
1 adult, Economy
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Find cheap flights from Houston 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
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Houston to Chesapeake
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Cheapest flights from Houston to ChesapeakeExplore the most affordable flight options available from Houston to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 29, 2026.
Explore the most affordable flight options available from Houston to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 29, 2026.
This CheapOair deal was found by Cheapflights users on 8/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/51:45 pm -
1 stop25h 26m
Mon 9/75:06 pm -
1 stop22h 26m
Deal found 8/29![Frontier logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 9/912:21 pm -
1 stop5h 27m
Fri 9/117:43 pm -
2 stops27h 47m
Deal found 8/24![Frontier logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:57 am -
1 stop6h 14m
Sun 9/209:50 pm -
2 stops34h 27m
Deal found 8/26![Multiple Airlines logo]()
$338
This Delta deal was found by Cheapflights users on 8/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/73:09 pm -
1 stop6h 21m
Sat 10/175:25 pm -
1 stop6h 38m
Deal found 8/25![Delta logo]()
$339
This United Airlines deal was found by Cheapflights users on 8/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:20 pm -
Nonstop3h 08m
Mon 9/286:15 am -
1 stop8h 04m
Deal found 8/25![United Airlines logo]()
$339
This Expedia deal was found by Cheapflights users on 8/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/303:25 pm -
1 stop23h 46m
Tue 9/15:06 pm -
1 stop22h 26m
Deal found 8/27![Frontier logo]()
$340
This CheapOair deal was found by Cheapflights users on 8/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/306:00 am -
1 stop5h 25m
Sun 9/65:06 pm -
1 stop15h 56m
Deal found 8/26![Frontier logo]()
$343
This Southwest deal was found by Cheapflights users on 8/25. 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.
Wed 10/2111:30 am -
2 stops7h 20m
Fri 10/236:05 pm -
1 stop7h 05m
Deal found 8/25![Southwest logo]()
$344
This Southwest deal was found by Cheapflights users on 8/25. 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.
Fri 10/23:45 pm -
2 stops6h 50m
Tue 10/64:45 pm -
2 stops7h 25m
Deal found 8/25![Southwest logo]()
$349
This United Airlines deal was found by Cheapflights users on 8/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:25 pm -
Nonstop3h 08m
Tue 9/156:10 am -
Nonstop3h 24m
Deal found 8/25![United Airlines logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1012:21 pm -
1 stop5h 27m
Sat 9/127:43 pm -
2 stops36h 34m
Deal found 8/25![Frontier logo]()
$352
This Southwest deal was found by Cheapflights users on 8/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/35:30 am -
2 stops8h 45m
Sun 10/46:20 am -
1 stop5h 00m
Deal found 8/27![Southwest logo]()
$354
Best flights from Houston to ChesapeakeDiscover carefully curated flight deals from Houston to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 29, 2026.
Discover carefully curated flight deals from Houston to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 29, 2026.
This Delta deal was found by Cheapflights users on 8/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:28 pm -
1 stop6h 17m
Sun 10/185:28 am -
1 stop5h 40m
Deal found 8/25![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 8/24. 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 10/161:30 pm -
2 stops6h 55m
Mon 10/195:50 pm -
1 stop7h 30m
Deal found 8/24![Southwest logo]()
$344
This United Airlines deal was found by Cheapflights users on 8/28. 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.
Fri 10/24:56 pm -
1 stop5h 48m
Mon 10/56:00 am -
Nonstop3h 22m
Deal found 8/28![United Airlines logo]()
$413
This Delta deal was found by Cheapflights users on 8/24. 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 10/66:09 am -
1 stop5h 11m
Sat 10/105:25 pm -
1 stop6h 38m
Deal found 8/24![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 8/24. 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 9/2310:10 am -
1 stop6h 10m
Sat 9/2611:35 am -
2 stops7h 45m
Deal found 8/24![Southwest logo]()
$344
This Southwest deal was found by Cheapflights users on 8/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/35:30 am -
2 stops8h 45m
Sun 10/46:20 am -
1 stop5h 00m
Deal found 8/27![Southwest logo]()
$354
This Delta deal was found by Cheapflights users on 8/29. 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 10/135:28 pm -
1 stop6h 17m
Tue 10/205:30 am -
1 stop5h 38m
Deal found 8/29![Delta logo]()
$359
This United Airlines deal was found by Cheapflights users on 8/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/34:56 pm -
1 stop5h 52m
Wed 10/76:00 am -
Nonstop3h 22m
Deal found 8/27![United Airlines logo]()
$429
This Southwest deal was found by Cheapflights users on 8/28. 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.
Mon 10/265:25 am -
1 stop7h 10m
Wed 11/113:05 pm -
1 stop6h 45m
Deal found 8/28![Southwest logo]()
$359
This Delta deal was found by Cheapflights users on 8/26. 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.
Mon 10/55:20 pm -
1 stop6h 22m
Sat 10/105:25 pm -
1 stop6h 38m
Deal found 8/26![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 8/26. 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.
Wed 10/711:12 am -
1 stop6h 16m
Sat 10/105:25 pm -
1 stop6h 38m
Deal found 8/26![Delta logo]()
$359
This Southwest deal was found by Cheapflights users on 8/25. 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.
Sat 10/311:50 am -
2 stops8h 35m
Wed 10/712:30 pm -
2 stops8h 25m
Deal found 8/25![Southwest logo]()
$379
This United Airlines deal was found by Cheapflights users on 8/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/134:45 pm -
1 stop5h 59m
Mon 11/166:00 am -
Nonstop3h 45m
Deal found 8/25![United Airlines logo]()
$465
This United Airlines deal was found by Cheapflights users on 8/29. 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.
Fri 9/186:25 pm -
Nonstop3h 02m
Sun 9/205:02 pm -
1 stop8h 25m
Deal found 8/29![United Airlines logo]()
$469
This Southwest deal was found by Cheapflights users on 8/24. 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 11/195:40 am -
1 stop6h 50m
Sun 11/223:25 pm -
1 stop8h 15m
Deal found 8/24![Southwest logo]()
$418
This United Airlines deal was found by Cheapflights users on 8/28. 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.
Tue 9/151:45 pm -
1 stop6h 56m
Tue 9/226:10 am -
Nonstop3h 24m
Deal found 8/28![United Airlines logo]()
$469
This United Airlines deal was found by Cheapflights users on 8/24. 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 10/82:51 pm -
1 stop7h 53m
Sat 10/106:00 am -
Nonstop3h 22m
Deal found 8/24![United Airlines logo]()
$479
This United Airlines deal was found by Cheapflights users on 8/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/161:53 pm -
2 stops8h 50m
Sun 9/205:02 pm -
1 stop8h 25m
Deal found 8/27![United Airlines logo]()
$484
This United Airlines deal was found by Cheapflights users on 8/24. 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.
Tue 9/221:53 pm -
2 stops8h 50m
Wed 9/306:15 am -
2 stops13h 37m
Deal found 8/24![United Airlines logo]()
$497
This United Airlines deal was found by Cheapflights users on 8/24. 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.
Fri 10/162:51 pm -
1 stop7h 53m
Mon 10/196:00 am -
Nonstop3h 22m
Deal found 8/24![United Airlines logo]()
$548
Last-minute flights from Houston to ChesapeakeDiscover last-minute flight deals from Houston to Chesapeake. Data last updated August 29, 2026 and is based on user searches.
Discover last-minute flight deals from Houston to Chesapeake. Data last updated August 29, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 8/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/303:25 pm -
1 stop23h 46m
Tue 9/15:06 pm -
1 stop22h 26m
Deal found 8/27![Frontier logo]()
$340
This CheapOair deal was found by Cheapflights users on 8/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/306:00 am -
1 stop5h 25m
Sun 9/65:06 pm -
1 stop15h 56m
Deal found 8/26![Frontier logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:57 am -
1 stop6h 14m
Sun 9/209:50 pm -
2 stops34h 27m
Deal found 8/26![Multiple Airlines logo]()
$338
This CheapOair deal was found by Cheapflights users on 8/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/51:45 pm -
1 stop25h 26m
Mon 9/75:06 pm -
1 stop22h 26m
Deal found 8/29![Frontier logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/86:00 am -
1 stop5h 25m
Tue 9/85:06 pm -
2 stops30h 24m
Deal found 8/25![Frontier logo]()
$356
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 9/912:21 pm -
1 stop5h 27m
Fri 9/117:43 pm -
2 stops27h 47m
Deal found 8/24![Frontier logo]()
$333
This United Airlines deal was found by Cheapflights users on 8/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:25 pm -
Nonstop3h 08m
Tue 9/156:10 am -
Nonstop3h 24m
Deal found 8/25![United Airlines logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1012:21 pm -
1 stop5h 27m
Sat 9/127:43 pm -
2 stops36h 34m
Deal found 8/25![Frontier logo]()
$352
This American Airlines deal was found by Cheapflights users on 8/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1011:31 am -
1 stop5h 38m
Tue 9/153:14 pm -
1 stop5h 34m
Deal found 8/25![American Airlines logo]()
$368
This Delta deal was found by Cheapflights users on 8/24. 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 9/2311:00 am -
1 stop6h 14m
Sat 9/266:00 am -
1 stop4h 59m
Deal found 8/24![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 8/24. 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 9/2310:10 am -
1 stop6h 10m
Sat 9/2611:35 am -
2 stops7h 45m
Deal found 8/24![Southwest logo]()
$344
This United Airlines deal was found by Cheapflights users on 8/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:20 pm -
Nonstop3h 08m
Mon 9/286:15 am -
1 stop8h 04m
Deal found 8/25![United Airlines logo]()
$339
One-way flights from Houston to ChesapeakeSearch for one-way flight options from Houston to Chesapeake. Find affordable one-way fares based on user searches. Data last updated August 29, 2026.
Search for one-way flight options from Houston to Chesapeake. Find affordable one-way fares based on user searches. Data last updated August 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/169:04 pm -
1 stop14h 25m
Deal found 8/26![Frontier logo]()
$85
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/149:12 pm -
1 stop14h 22m
Deal found 8/26![Frontier logo]()
$87
This Super.com deal was found by Cheapflights users on 8/25. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1512:21 pm -
1 stop5h 27m
Deal found 8/25![Frontier logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:05 am -
1 stop5h 29m
Deal found 8/25![Frontier logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/276:08 am -
1 stop5h 21m
Deal found 8/27![Frontier logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/169:12 pm -
1 stop16h 43m
Deal found 8/25![Frontier logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 8/29. 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 9/289:04 pm -
1 stop14h 25m
Deal found 8/29![Frontier logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 10/85:55 am -
1 stop5h 39m
Deal found 8/24![Frontier logo]()
$118
This American Airlines deal was found by Cheapflights users on 8/24. 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.
Tue 10/62:08 pm -
1 stop7h 41m
Deal found 8/24![American Airlines logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/158:25 am -
2 stops26h 50m
Deal found 8/25![Multiple Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/99:12 pm -
1 stop16h 43m
Deal found 8/25![Frontier logo]()
$127
This Southwest deal was found by Cheapflights users on 8/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:05 am -
1 stop7h 25m
Deal found 8/26![Southwest logo]()
$170
Find flight deals from Houston to Chesapeake
Keep the following information in mind while searching for Houston to Chesapeake flight deals. Data was last updated August 29, 2026.
Round-trip from | $174 (Kiwi.com) |
|---|---|
One-way from | $85 (Kiwi.com) |
Popular in | April |
Cheapest in | September |
Average price | $358 |
Cheapflights Fare Finder
Customize your flight search to find flights from Houston 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 7,457,451 searches. Data last updated August 29, 2026.
Use the filters below to find and compare flights from Houston to Chesapeake that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
HoustonNorfolk
HOU Houston Hobby - ORF Norfolk
HOUORF
Houston Hobby
Fri 10/16
5:28 pm-12:45 am
1 stop6h 17m
Norfolk
Sun 10/18
5:28 am-10:08 am
1 stop5h 40m
$339
HoustonNorfolk
HOU Houston Hobby - ORF Norfolk
HOUORF
Houston Hobby
Tue 10/6
6:09 am-12:20 pm
1 stop5h 11m
Norfolk
Sat 10/10
5:25 pm-11:03 pm
1 stop6h 38m
$339
HoustonNorfolk
HOU Houston Hobby - ORF Norfolk
HOUORF
Houston Hobby
Fri 10/16
1:30 pm-9:25 pm
2 stops6h 55m
Norfolk
Mon 10/19
5:50 pm-12:20 am
1 stop7h 30m
$344
HoustonNorfolk
HOU Houston Hobby - ORF Norfolk
HOUORF
Houston Hobby
Wed 9/23
10:10 am-5:20 pm
1 stop6h 10m
Norfolk
Sat 9/26
11:35 am-6:20 pm
2 stops7h 45m
$344
HoustonNorfolk
HOU Houston Hobby - ORF Norfolk
HOUORF
Houston Hobby
Sat 10/3
5:30 am-3:15 pm
2 stops8h 45m
Norfolk
Sun 10/4
6:20 am-10:20 am
1 stop5h 00m
$354
HoustonNorfolk
HOU Houston Hobby - ORF Norfolk
HOUORF
Houston Hobby
Tue 10/13
5:28 pm-12:45 am
1 stop6h 17m
Norfolk
Tue 10/20
5:30 am-10:08 am
1 stop5h 38m
$359
HoustonNorfolk
HOU Houston Hobby - ORF Norfolk
HOUORF
Houston Hobby
Mon 10/26
5:25 am-1:35 pm
1 stop7h 10m
Norfolk
Wed 11/11
3:05 pm-8:50 pm
1 stop6h 45m
$359
HoustonNorfolk
HOU Houston Hobby - ORF Norfolk
HOUORF
Houston Hobby
Mon 10/5
5:20 pm-12:42 am
1 stop6h 22m
Norfolk
Sat 10/10
5:25 pm-11:03 pm
1 stop6h 38m
$359
HoustonNorfolk
HOU Houston Hobby - ORF Norfolk
HOUORF
Houston Hobby
Wed 10/7
11:12 am-6:28 pm
1 stop6h 16m
Norfolk
Sat 10/10
5:25 pm-11:03 pm
1 stop6h 38m
$359
HoustonNorfolk
HOU Houston Hobby - ORF Norfolk
HOUORF
Houston Hobby
Sat 10/3
11:50 am-9:25 pm
2 stops8h 35m
Norfolk
Wed 10/7
12:30 pm-7:55 pm
2 stops8h 25m
$379
Showing 1-10 of 40 resultsSorted by cheapest first
Best time to book a flight from Houston to Chesapeake
Have a flexible travel schedule? Discover the best time to fly to Chesapeake from Houston with our price prediction graph.
IAH-ORF
HOU-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 Houston to Chesapeake
HO1-C6E
IAH-ORF
HOU-ORF
What is the cheapest time of day to fly from HOU to C6E?
Find hourly flight availability from Houston 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 29, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 16% on flights from Houston to Chesapeake by exploring options for tickets in the afternoon.
How much does it cost to fly round-trip from Houston to Chesapeake?
Airfare is below average for this route at the moment.
Houston to Chesapeake flights typically cost between $328 and $449 in November.The cheapest round-trip price found within the last 5 days was $174 on Frontier (Nov 12-Nov 17).
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 29, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited Airlines from Houston to Chesapeake. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Related info for your journey
Find useful and relevant information for your journey from Houston 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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Alternative routes for Houston to Chesapeake
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Chesapeake by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Houston to Chesapeake by cabin class
Find flights from Houston to Chesapeake, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Houston and Chesapeake flights
Browse other Houston and Chesapeake flight options. Last updated on August 29, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Houston to Chesapeake
Discover the top 5 airlines that operate flights from Houston 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 7,457,451 searches. Data last updated August 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$144 | Average$204 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$194 | Average$395 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$204 | Average$432 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$226 | Average$357 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$239 | Average$434 | FlexibilityNo cancel fee | On-time69% |