$59+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — RIC
Jun 21 — Jun 281
Round-trip
1 adult, Economy
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Find cheap flights from Houston to Chesapeake with Cheapflights
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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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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 May 22, 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 May 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 7/218:02 pm
IAH
- ORF
1 stop14h 19m
Frontier
Tue 8/189:56 pm
ORF
- IAH
1 stop11h 51m
Frontier
Deal found 5/18![Frontier logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 5/17. 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 6/98:02 pm
IAH
- ORF
1 stop14h 24m
Frontier
Tue 6/1612:21 pm
ORF
- IAH
1 stop22h 46m
Frontier
Deal found 5/17![Frontier logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 5/17. 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 6/228:55 pm
IAH
- ORF
1 stop13h 31m
Frontier
Tue 6/3012:21 pm
ORF
- IAH
1 stop20h 02m
Frontier
Deal found 5/17![Frontier logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 7/218:20 am
IAH
- ORF
2 stops8h 12m
Multiple Airlines
Tue 8/189:56 pm
ORF
- IAH
1 stop11h 51m
Multiple Airlines
Deal found 5/18![Multiple Airlines logo]()
$186
This Frontier deal was found by Cheapflights users on 5/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/141:14 pm
IAH
- ORF
1 stop6h 25m
Frontier
Wed 7/159:35 pm
ORF
- IAH
1 stop12h 10m
Frontier
Deal found 5/17![Frontier logo]()
$190
This Frontier deal was found by Cheapflights users on 5/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/191:07 pm
IAH
- ORF
1 stop6h 54m
Frontier
Sat 8/2212:00 pm
ORF
- IAH
1 stop11h 48m
Frontier
Deal found 5/17![Frontier logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 5/17. 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 6/168:18 am
IAH
- ORF
2 stops26h 08m
Frontier
Tue 6/2312:21 pm
ORF
- IAH
1 stop20h 02m
Frontier
Deal found 5/17![Frontier logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 6/1711:12 am
IAH
- ORF
1 stop23h 14m
Frontier
Wed 6/2412:21 pm
ORF
- IAH
1 stop20h 02m
Frontier
Deal found 5/18![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 6/238:02 pm
IAH
- ORF
1 stop14h 24m
Frontier
Sun 6/2812:21 pm
ORF
- IAH
1 stop20h 02m
Frontier
Deal found 5/18![Frontier logo]()
$239
This Southwest deal was found by Cheapflights users on 5/19. 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 6/164:30 pm
HOU
- ORF
1 stop7h 15m
Southwest
Tue 6/237:00 pm
ORF
- HOU
1 stop5h 35m
Southwest
Deal found 5/19![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 5/19. 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 7/84:30 pm
HOU
- ORF
1 stop7h 15m
Southwest
Sat 7/115:40 pm
ORF
- HOU
1 stop7h 25m
Southwest
Deal found 5/19![Southwest logo]()
$319
This Southwest deal was found by Cheapflights users on 5/18. 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 6/193:35 pm
HOU
- ORF
2 stops7h 00m
Southwest
Tue 6/237:00 pm
ORF
- HOU
1 stop5h 35m
Southwest
Deal found 5/18![Southwest logo]()
$324
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 May 22, 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 May 22, 2026.
This United Airlines deal was found by Cheapflights users on 5/19. 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 6/164:35 pm
IAH
- ORF
1 stop6h 09m
United Airlines
Tue 6/236:15 am
ORF
- IAH
Nonstop3h 05m
United Airlines
Deal found 5/19![United Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 5/19. 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 7/287:00 am
HOU
- ORF
2 stops7h 50m
Southwest
Mon 8/36:10 pm
ORF
- HOU
2 stops6h 55m
Southwest
Deal found 5/19![Southwest logo]()
$329
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:00 am
HOU
- ORF
1 stop5h 49m
Delta
Mon 9/285:30 am
ORF
- HOU
1 stop4h 45m
Delta
Deal found 5/20![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 5/22. 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 6/193:35 pm
HOU
- ORF
2 stops7h 00m
Southwest
Mon 6/226:10 pm
ORF
- HOU
2 stops6h 55m
Southwest
Deal found 5/22![Southwest logo]()
$339
This Southwest deal was found by Cheapflights users on 5/18. 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 6/87:00 pm
HOU
- ORF
2 stops13h 25m
Southwest
Thu 6/115:35 am
ORF
- HOU
1 stop7h 40m
Southwest
Deal found 5/18![Southwest logo]()
$340
This United Airlines deal was found by Cheapflights users on 5/18. 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 6/266:24 pm
IAH
- ORF
Nonstop3h 06m
United Airlines
Sat 7/46:15 am
ORF
- IAH
Nonstop3h 05m
United Airlines
Deal found 5/18![United Airlines logo]()
$389
This Southwest deal was found by Cheapflights users on 5/18. 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 6/163:55 pm
HOU
- ORF
1 stop5h 40m
Southwest
Wed 6/173:40 pm
ORF
- HOU
2 stops5h 55m
Southwest
Deal found 5/18![Southwest logo]()
$354
This United Airlines deal was found by Cheapflights users on 5/20. 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 7/76:24 pm
IAH
- ORF
Nonstop3h 06m
United Airlines
Thu 7/306:15 am
ORF
- IAH
Nonstop3h 05m
United Airlines
Deal found 5/20![United Airlines logo]()
$399
This Southwest deal was found by Cheapflights users on 5/19. 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 6/162:00 pm
HOU
- ORF
2 stops7h 35m
Southwest
Tue 6/233:40 pm
ORF
- HOU
2 stops5h 55m
Southwest
Deal found 5/19![Southwest logo]()
$359
This United Airlines deal was found by Cheapflights users on 5/19. 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 6/122:31 pm
IAH
- ORF
1 stop8h 13m
United Airlines
Sun 6/146:15 am
ORF
- IAH
Nonstop3h 05m
United Airlines
Deal found 5/19![United Airlines logo]()
$404
This Southwest deal was found by Cheapflights users on 5/22. 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 6/95:00 am
HOU
- ORF
1 stop5h 45m
Southwest
Fri 6/127:15 pm
ORF
- HOU
1 stop5h 55m
Southwest
Deal found 5/22![Southwest logo]()
$359
This United Airlines deal was found by Cheapflights users on 5/21. 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 6/276:24 pm
IAH
- ORF
Nonstop3h 07m
United Airlines
Tue 6/305:00 pm
ORF
- IAH
1 stop8h 34m
United Airlines
Deal found 5/21![United Airlines logo]()
$433
This United Airlines deal was found by Cheapflights users on 5/18. 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 7/156:24 pm
IAH
- ORF
Nonstop3h 06m
United Airlines
Sun 7/196:15 am
ORF
- IAH
Nonstop3h 05m
United Airlines
Deal found 5/18![United Airlines logo]()
$454
This United Airlines deal was found by Cheapflights users on 5/17. 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.
Mon 5/256:24 pm
IAH
- ORF
Nonstop3h 06m
United Airlines
Fri 6/55:44 pm
ORF
- IAH
1 stop6h 59m
United Airlines
Deal found 5/17![United Airlines logo]()
$456
This United Airlines deal was found by Cheapflights users on 5/17. 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.
Mon 6/226:24 pm
IAH
- ORF
Nonstop3h 06m
United Airlines
Tue 6/306:15 am
ORF
- IAH
Nonstop3h 05m
United Airlines
Deal found 5/17![United Airlines logo]()
$463
This United Airlines deal was found by Cheapflights users on 5/18. 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 6/235:20 pm
IAH
- ORF
1 stop6h 37m
United Airlines
Sun 6/286:15 am
ORF
- IAH
Nonstop3h 05m
United Airlines
Deal found 5/18![United Airlines logo]()
$476
This United Airlines deal was found by Cheapflights users on 5/19. 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 6/106:24 pm
IAH
- ORF
Nonstop3h 06m
United Airlines
Sun 6/146:15 am
ORF
- IAH
Nonstop3h 05m
United Airlines
Deal found 5/19![United Airlines logo]()
$478
Last-minute flights from Houston to ChesapeakeDiscover last-minute flight deals from Houston to Chesapeake. Data last updated May 22, 2026 and is based on user searches.
Discover last-minute flight deals from Houston to Chesapeake. Data last updated May 22, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 5/18. 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.
Mon 6/87:20 pm
IAH
- ORF
1 stop24h 20m
Frontier
Thu 6/119:35 pm
ORF
- IAH
1 stop21h 54m
Frontier
Deal found 5/18![Frontier logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 5/17. 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 6/98:02 pm
IAH
- ORF
1 stop14h 24m
Frontier
Tue 6/1612:21 pm
ORF
- IAH
1 stop22h 46m
Frontier
Deal found 5/17![Frontier logo]()
$162
This Southwest deal was found by Cheapflights users on 5/17. 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 6/95:00 am
HOU
- ORF
1 stop5h 45m
Southwest
Tue 6/167:00 pm
ORF
- HOU
1 stop5h 35m
Southwest
Deal found 5/17![Southwest logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 5/17. 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 6/168:18 am
IAH
- ORF
2 stops26h 08m
Frontier
Tue 6/2312:21 pm
ORF
- IAH
1 stop20h 02m
Frontier
Deal found 5/17![Frontier logo]()
$212
This Southwest deal was found by Cheapflights users on 5/17. 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 6/164:30 pm
HOU
- ORF
1 stop7h 15m
Southwest
Tue 6/237:00 pm
ORF
- HOU
1 stop5h 35m
Southwest
Deal found 5/17![Southwest logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 6/1711:12 am
IAH
- ORF
1 stop23h 14m
Frontier
Wed 6/2412:21 pm
ORF
- IAH
1 stop20h 02m
Frontier
Deal found 5/18![Frontier logo]()
$213
This Southwest deal was found by Cheapflights users on 5/18. 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 6/193:35 pm
HOU
- ORF
2 stops7h 00m
Southwest
Tue 6/237:00 pm
ORF
- HOU
1 stop5h 35m
Southwest
Deal found 5/18![Southwest logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 5/17. 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 6/228:55 pm
IAH
- ORF
1 stop13h 31m
Frontier
Tue 6/3012:21 pm
ORF
- IAH
1 stop20h 02m
Frontier
Deal found 5/17![Frontier logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 5/17. 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 6/228:55 pm
IAH
- ORF
1 stop13h 31m
Frontier
Sun 6/2812:21 pm
ORF
- IAH
1 stop20h 02m
Frontier
Deal found 5/17![Frontier logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 5/18. 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 6/238:02 pm
IAH
- ORF
1 stop14h 24m
Frontier
Sun 6/2812:21 pm
ORF
- IAH
1 stop20h 02m
Frontier
Deal found 5/18![Frontier logo]()
$239
This Expedia deal was found by Cheapflights users on 5/18. 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.
Thu 6/257:24 pm
IAH
- ORF
1 stop24h 16m
Frontier
Sun 7/59:35 pm
ORF
- IAH
1 stop12h 10m
Frontier
Deal found 5/18![Frontier logo]()
$250
This Southwest deal was found by Cheapflights users on 5/18. 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 6/268:40 pm
HOU
- ORF
1 stop11h 35m
Southwest
Tue 7/74:30 pm
ORF
- HOU
2 stops7h 40m
Southwest
Deal found 5/18![Southwest logo]()
$330
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 May 22, 2026.
Search for one-way flight options from Houston to Chesapeake. Find affordable one-way fares based on user searches. Data last updated May 22, 2026.
This Trip.com deal was found by Cheapflights users on 5/18. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/128:55 pm
IAH
- ORF
1 stop13h 26m
Frontier
Deal found 5/18![Frontier logo]()
$59
This Kiwi.com deal was found by Cheapflights users on 5/20. 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.
Sat 7/118:02 pm
IAH
- ORF
1 stop14h 13m
Frontier
Deal found 5/20![Frontier logo]()
$78
This Super.com deal was found by Cheapflights users on 5/18. 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.
Wed 7/221:14 pm
IAH
- ORF
1 stop6h 25m
Frontier
Deal found 5/18![Frontier logo]()
$92
This Trip.com deal was found by Cheapflights users on 5/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/268:55 pm
IAH
- ORF
1 stop13h 26m
Frontier
Deal found 5/21![Frontier logo]()
$93
This Frontier deal was found by Cheapflights users on 5/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/291:14 pm
IAH
- ORF
1 stop6h 25m
Frontier
Deal found 5/17![Frontier logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 5/21. 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 6/198:55 pm
IAH
- ORF
1 stop13h 26m
Frontier
Deal found 5/21![Frontier logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 5/17. 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 6/118:55 am
IAH
- ORF
2 stops25h 31m
Frontier
Deal found 5/17![Frontier logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 5/20. 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 6/238:02 pm
IAH
- ORF
1 stop14h 24m
Frontier
Deal found 5/20![Frontier logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 5/19. 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 6/228:55 pm
IAH
- ORF
1 stop13h 31m
Frontier
Deal found 5/19![Frontier logo]()
$113
This American Airlines deal was found by Cheapflights users on 5/18. 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.
Wed 8/125:41 am
HOU
- ORF
1 stop7h 40m
American Airlines
Deal found 5/18![American Airlines logo]()
$155
This Southwest deal was found by Cheapflights users on 5/18. 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 8/126:25 am
HOU
- ORF
2 stops7h 05m
Southwest
Deal found 5/18![Southwest logo]()
$160
This Southwest deal was found by Cheapflights users on 5/18. 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 7/33:25 pm
HOU
- ORF
1 stop7h 10m
Southwest
Deal found 5/18![Southwest logo]()
$165
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 May 22, 2026.
Round-trip from | $134 (Kiwi.com) |
|---|---|
One-way from | $59 (Trip.com) |
Popular in | April |
Cheapest in | August |
Average price | $427 |
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 2,558,603 searches. Data last updated May 22, 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
IAH - ORF
IAHORF
Houston George Bush Intcntl
Tue 6/16
4:35 pm-11:44 pm
1 stop6h 09m
Norfolk
Tue 6/23
6:15 am-8:20 am
Nonstop3h 05m
$309
HoustonNorfolk
HOU - ORF
HOUORF
Houston Hobby
Tue 7/28
7:00 am-3:50 pm
2 stops7h 50m
Norfolk
Mon 8/3
6:10 pm-12:05 am
2 stops6h 55m
$329
HoustonNorfolk
HOU - ORF
HOUORF
Houston Hobby
Thu 9/24
6:00 am-12:49 pm
1 stop5h 49m
Norfolk
Mon 9/28
5:30 am-9:15 am
1 stop4h 45m
$329
HoustonNorfolk
HOU - ORF
HOUORF
Houston Hobby
Fri 6/19
3:35 pm-11:35 pm
2 stops7h 00m
Norfolk
Mon 6/22
6:10 pm-12:05 am
2 stops6h 55m
$339
HoustonNorfolk
HOU - ORF
HOUORF
Houston Hobby
Mon 6/8
7:00 pm-9:25 am
2 stops13h 25m
Norfolk
Thu 6/11
5:35 am-12:15 pm
1 stop7h 40m
$340
HoustonNorfolk
HOU - ORF
HOUORF
Houston Hobby
Tue 6/16
3:55 pm-10:35 pm
1 stop5h 40m
Norfolk
Wed 6/17
3:40 pm-8:35 pm
2 stops5h 55m
$354
HoustonNorfolk
HOU - ORF
HOUORF
Houston Hobby
Tue 6/16
2:00 pm-10:35 pm
2 stops7h 35m
Norfolk
Tue 6/23
3:40 pm-8:35 pm
2 stops5h 55m
$359
HoustonNorfolk
HOU - ORF
HOUORF
Houston Hobby
Tue 6/9
5:00 am-11:45 am
1 stop5h 45m
Norfolk
Fri 6/12
7:15 pm-12:10 am
1 stop5h 55m
$359
Quickest round-trip
HoustonNorfolk
IAH - ORF
IAHORF
Houston George Bush Intcntl
Fri 6/26
6:24 pm-10:30 pm
Nonstop3h 06m
Norfolk
Sat 7/4
6:15 am-8:20 am
Nonstop3h 05m
$389
HoustonNorfolk
IAH - ORF
IAHORF
Houston George Bush Intcntl
Tue 7/7
6:24 pm-10:30 pm
Nonstop3h 06m
Norfolk
Thu 7/30
6:15 am-8:20 am
Nonstop3h 05m
$399
Showing 1-10 of 36 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 May 22, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 18% on flights from Houston to Chesapeake by exploring options for tickets in the morning.
How much does it cost to fly round-trip from Houston 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 May 22, 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.
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
7.9
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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
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Complete your trip
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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 May 22, 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 2,558,603 searches. Data last updated May 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$144 | Average$198 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$194 | Average$373 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$204 | Average$401 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$216 | Average$345 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$229 | Average$428 | FlexibilityNo cancel fee | On-time69% |