$158+ Cheap flights from Oakland, CA (OAK) to Chesapeake, VA
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — RIC
Oct 20 — Oct 271
Round-trip
1 adult, Economy
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Find cheap flights from Oakland 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.Cheap flight deals from Oakland to Chesapeake
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Best
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One-way
Cheapest flights from Oakland to ChesapeakeExplore the most affordable flight options available from Oakland to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 20, 2026.
Explore the most affordable flight options available from Oakland to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 20, 2026.
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/245:02 pm -
2 stops15h 26m
Wed 10/288:10 am -
2 stops11h 12m
Deal found 9/14![Delta logo]()
$350
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:47 pm -
2 stops20h 51m
Mon 10/269:28 am -
1 stop29h 25m
Deal found 9/14![Multiple Airlines logo]()
$361
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/245:02 pm -
2 stops15h 26m
Thu 10/2912:30 pm -
2 stops14h 26m
Deal found 9/14![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/245:02 pm -
2 stops15h 26m
Fri 10/305:15 pm -
2 stops9h 41m
Deal found 9/14![Delta logo]()
$395
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:20 pm -
1 stop24h 22m
Tue 10/271:44 pm -
2 stops25h 09m
Deal found 9/14![Multiple Airlines logo]()
$403
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2012:47 pm -
2 stops26h 59m
Fri 10/309:28 am -
1 stop10h 32m
Deal found 9/14![Multiple Airlines logo]()
$404
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/205:02 pm -
2 stops28h 04m
Wed 10/288:10 am -
2 stops11h 12m
Deal found 9/14![Delta logo]()
$406
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2012:47 pm -
2 stops26h 59m
Mon 10/269:28 am -
1 stop29h 25m
Deal found 9/14![Multiple Airlines logo]()
$415
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:20 pm -
1 stop24h 22m
Thu 10/291:31 pm -
2 stops22h 52m
Deal found 9/14![Multiple Airlines logo]()
$418
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:20 pm -
2 stops16h 14m
Fri 10/309:28 am -
1 stop10h 32m
Deal found 9/14![Multiple Airlines logo]()
$427
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:00 am -
2 stops15h 06m
Thu 10/2912:30 pm -
2 stops14h 26m
Deal found 9/14![Delta logo]()
$429
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:25 am -
2 stops8h 45m
Tue 10/274:45 pm -
2 stops9h 35m
Deal found 9/14![Southwest logo]()
$433
Best flights from Oakland to ChesapeakeDiscover carefully curated flight deals from Oakland to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 20, 2026.
Discover carefully curated flight deals from Oakland to Chesapeake that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 20, 2026.
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:41 pm -
2 stops19h 39m
Fri 10/305:15 pm -
2 stops9h 41m
Deal found 9/14![Delta logo]()
$451
This Southwest deal was found by Cheapflights users on 9/16. 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 10/1611:55 pm -
1 stop8h 10m
Thu 10/227:00 pm -
1 stop8h 15m
Deal found 9/16![Southwest logo]()
$477
This Delta deal was found by Cheapflights users on 9/16. 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 10/165:02 pm -
2 stops15h 20m
Thu 10/225:05 pm -
2 stops9h 51m
Deal found 9/16![Delta logo]()
$487
This Southwest deal was found by Cheapflights users on 9/19. 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.
Sat 1/97:40 pm -
2 stops10h 40m
Sat 1/166:25 am -
2 stops12h 00m
Deal found 9/19![Southwest logo]()
$503
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/67:35 pm -
2 stops10h 45m
Tue 10/137:50 am -
1 stop7h 50m
Deal found 9/15![Southwest logo]()
$516
This Delta deal was found by Cheapflights users on 9/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:00 pm -
2 stops14h 42m
Tue 10/63:13 pm -
2 stops11h 43m
Deal found 9/17![Delta logo]()
$556
This Southwest deal was found by Cheapflights users on 9/17. 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.
Fri 10/211:55 pm -
1 stop8h 10m
Tue 10/67:50 am -
1 stop7h 50m
Deal found 9/17![Southwest logo]()
$617
This Delta deal was found by Cheapflights users on 9/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:55 am -
2 stops31h 10m
Thu 11/267:18 am -
2 stops13h 57m
Deal found 9/18![Delta logo]()
$626
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:35 pm -
2 stops10h 45m
Sun 10/257:25 pm -
1 stop7h 45m
Deal found 9/14![Southwest logo]()
$793
This Southwest deal was found by Cheapflights users on 9/16. 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 10/217:35 pm -
2 stops10h 40m
Sun 10/257:25 pm -
1 stop7h 45m
Deal found 9/16![Southwest logo]()
$852
This Southwest deal was found by Cheapflights users on 9/18. 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 11/2411:50 pm -
1 stop7h 40m
Sun 11/298:20 pm -
1 stop8h 25m
Deal found 9/18![Southwest logo]()
$883
Last-minute flights from Oakland to ChesapeakeDiscover last-minute flight deals from Oakland to Chesapeake. Data last updated September 20, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Chesapeake. Data last updated September 20, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:20 pm -
2 stops16h 14m
Fri 10/309:28 am -
1 stop10h 32m
Deal found 9/14![Multiple Airlines logo]()
$427
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2012:47 pm -
2 stops26h 59m
Fri 10/309:28 am -
1 stop10h 32m
Deal found 9/14![Multiple Airlines logo]()
$404
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/205:02 pm -
2 stops28h 04m
Wed 10/288:10 am -
2 stops11h 12m
Deal found 9/14![Delta logo]()
$406
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2012:47 pm -
2 stops26h 59m
Mon 10/269:28 am -
1 stop29h 25m
Deal found 9/14![Multiple Airlines logo]()
$415
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:00 am -
2 stops15h 06m
Thu 10/2912:30 pm -
2 stops14h 26m
Deal found 9/14![Delta logo]()
$429
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:47 pm -
2 stops20h 51m
Mon 10/269:28 am -
1 stop29h 25m
Deal found 9/14![Multiple Airlines logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:20 pm -
1 stop24h 22m
Tue 10/271:44 pm -
2 stops25h 09m
Deal found 9/14![Multiple Airlines logo]()
$403
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:20 pm -
1 stop24h 22m
Thu 10/291:31 pm -
2 stops22h 52m
Deal found 9/14![Multiple Airlines logo]()
$418
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:25 am -
2 stops8h 45m
Tue 10/274:45 pm -
2 stops9h 35m
Deal found 9/14![Southwest logo]()
$433
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/245:02 pm -
2 stops15h 26m
Wed 10/288:10 am -
2 stops11h 12m
Deal found 9/14![Delta logo]()
$350
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/245:02 pm -
2 stops15h 26m
Thu 10/2912:30 pm -
2 stops14h 26m
Deal found 9/14![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/245:02 pm -
2 stops15h 26m
Fri 10/305:15 pm -
2 stops9h 41m
Deal found 9/14![Delta logo]()
$395
One-way flights from Oakland to ChesapeakeSearch for one-way flight options from Oakland to Chesapeake. Find affordable one-way fares based on user searches. Data last updated September 20, 2026.
Search for one-way flight options from Oakland to Chesapeake. Find affordable one-way fares based on user searches. Data last updated September 20, 2026.
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:35 pm -
2 stops10h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$158
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:02 pm -
2 stops15h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Delta logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 9/19. 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.
Thu 10/2210:17 am -
3 stops47h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Multiple Airlines logo]()
$214
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/155:35 am -
1 stop7h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$239
This Southwest deal was found by Cheapflights users on 9/16. 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 11/2411:50 pm -
2 stops9h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 9/2212:47 pm -
2 stops27h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 9/19. 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.
Thu 10/225:20 pm -
2 stops18h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Frontier logo]()
$261
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1111:55 pm -
1 stop8h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$275
This Southwest deal was found by Cheapflights users on 9/18. 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 10/211:55 pm -
1 stop8h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Southwest logo]()
$309
Find flight deals from Oakland to Chesapeake
Keep the following information in mind while searching for Oakland to Chesapeake flight deals. Data was last updated September 20, 2026.
Round-trip from | $350 (Delta) |
|---|---|
One-way from | $158 (Southwest) |
Popular in | April |
Cheapest in | February |
Average price | $527 |
Cheapflights Fare Finder
Customize your flight search to find flights from Oakland 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 September 20, 2026.
Use the filters below to find and compare flights from Oakland to Chesapeake that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
OaklandNorfolk
OAK Oakland - ORF Norfolk
OAKORF
Oakland
Thu 10/22
10:17 am-8:42 pm
1 stop31h 25m
Norfolk
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$233
Quickest round-trip
OaklandNorfolk
OAK Oakland - ORF Norfolk
OAKORF
Oakland
Sun 11/15
5:35 am-3:55 pm
1 stop7h 20m
Norfolk
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$239
OaklandNorfolk
OAK Oakland - ORF Norfolk
OAKORF
Oakland
Tue 11/24
11:50 pm-12:45 pm
2 stops9h 55m
Norfolk
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$244
OaklandNorfolk
OAK Oakland - ORF Norfolk
OAKORF
Oakland
Wed 11/25
11:50 pm-11:45 am
2 stops8h 55m
Norfolk
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$244
OaklandNorfolk
OAK Oakland - ORF Norfolk
OAKORF
Oakland
Sun 11/22
10:20 am-11:35 pm
2 stops10h 15m
Norfolk
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$264
OaklandNorfolk
OAK Oakland - ORF Norfolk
OAKORF
Oakland
Sun 10/11
11:55 pm-11:00 am
1 stop8h 05m
Norfolk
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$275
OaklandNorfolk
OAK Oakland - ORF Norfolk
OAKORF
Oakland
Fri 10/2
11:55 pm-11:05 am
1 stop8h 10m
Norfolk
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$309
OaklandNorfolk
OAK Oakland - ORF Norfolk
OAKORF
Oakland
Fri 10/2
5:00 pm-10:42 am
2 stops14h 42m
Norfolk
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$314
OaklandNorfolk
OAK Oakland - ORF Norfolk
OAKORF
Oakland
Wed 10/21
12:41 pm-11:20 am
2 stops19h 39m
Norfolk
Fri 10/30
5:15 pm-11:56 pm
2 stops9h 41m
$451
OaklandNorfolk
OAK Oakland - ORF Norfolk
OAKORF
Oakland
Fri 10/16
11:55 pm-11:05 am
1 stop8h 10m
Norfolk
Thu 10/22
7:00 pm-12:15 am
1 stop8h 15m
$477
Showing 1-10 of 19 resultsSorted by cheapest first
Best time to book a flight from Oakland to Chesapeake
Have a flexible travel schedule? Discover the best time to fly to Chesapeake from Oakland with our price prediction graph.
OAK-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 Oakland to Chesapeake
OAK-C6E
OAK-ORF
How much does it cost to fly round-trip from Oakland, California to Chesapeake?
Airfare is below average for this route at the moment.
Oakland, California to Chesapeake flights typically cost between $432 and $598 in October.The cheapest round-trip price found within the last 5 days was $350 on Delta (Oct 24-Oct 28).
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 September 20, 2026.
See what other customers who have flown with Southwest from Oakland to Chesapeake have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Related info for your journey
Find useful and relevant information for your journey from Oakland 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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Oakland and Chesapeake flights
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Other flights from Oakland
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Oakland to Chesapeake flights
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Top airline flying from Oakland to Chesapeake
Discover the top airline that operate flights from Oakland 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 September 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$368 | Average$537 | FlexibilityNo cancel fee | On-time63% |