$156+ Cheap flights from Oakland, CA (OAK) 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 9/7. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — RIC
Sep 3 — Sep 101
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
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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 Oakland to Chesapeake
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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 August 4, 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 August 4, 2026.
This Southwest deal was found by Cheapflights users on 8/3. 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 10/1411:55 pm -
1 stop8h 05m
Mon 10/197:00 pm -
1 stop8h 10m
Deal found 8/3![Southwest logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 9/112:13 pm -
2 stops21h 12m
Mon 9/78:16 am -
1 stop30h 02m
Deal found 8/2![Multiple Airlines logo]()
$381
This Southwest deal was found by Cheapflights users on 7/30. 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 9/2711:55 pm -
1 stop9h 15m
Wed 9/306:15 pm -
1 stop7h 55m
Deal found 7/30![Southwest logo]()
$394
This Southwest deal was found by Cheapflights users on 8/3. 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 9/1511:55 pm -
1 stop9h 10m
Sun 9/205:05 pm -
2 stops9h 35m
Deal found 8/3![Southwest logo]()
$417
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1811:55 pm -
1 stop8h 00m
Mon 9/2112:50 pm -
1 stop9h 30m
Deal found 8/1![Southwest logo]()
$435
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 August 4, 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 August 4, 2026.
This Southwest deal was found by Cheapflights users on 8/3. 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 10/1411:55 pm -
1 stop8h 05m
Mon 10/197:00 pm -
1 stop8h 10m
Deal found 8/3![Southwest logo]()
$347
This Southwest deal was found by Cheapflights users on 7/30. 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 9/2711:55 pm -
1 stop9h 15m
Wed 9/306:15 pm -
1 stop7h 55m
Deal found 7/30![Southwest logo]()
$394
This Southwest deal was found by Cheapflights users on 8/3. 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 9/1511:55 pm -
1 stop9h 10m
Sun 9/205:05 pm -
2 stops9h 35m
Deal found 8/3![Southwest logo]()
$417
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1811:55 pm -
1 stop8h 00m
Mon 9/218:00 am -
2 stops16h 25m
Deal found 8/1![Southwest logo]()
$417
This Southwest deal was found by Cheapflights users on 8/2. 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
Sun 10/256:20 am -
2 stops10h 55m
Deal found 8/2![Southwest logo]()
$518
This Southwest deal was found by Cheapflights users on 8/3. 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 9/111:55 pm -
1 stop9h 10m
Mon 9/76:45 pm -
1 stop7h 25m
Deal found 8/3![Southwest logo]()
$681
Last-minute flights from Oakland to ChesapeakeDiscover last-minute flight deals from Oakland to Chesapeake. Data last updated August 4, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Chesapeake. Data last updated August 4, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 7/31. 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 8/1812:33 pm -
2 stops26h 16m
Sat 8/227:17 am -
2 stops11h 57m
Deal found 7/31![Delta logo]()
$679
This Delta deal was found by Cheapflights users on 7/31. 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 8/1812:33 pm -
2 stops26h 16m
Tue 8/257:00 am -
2 stops19h 56m
Deal found 7/31![Delta logo]()
$695
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 9/112:13 pm -
2 stops21h 12m
Mon 9/78:16 am -
1 stop30h 02m
Deal found 8/2![Multiple Airlines logo]()
$381
This Southwest deal was found by Cheapflights users on 8/3. 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 9/111:55 pm -
1 stop9h 10m
Mon 9/76:45 pm -
1 stop7h 25m
Deal found 8/3![Southwest logo]()
$681
This Southwest deal was found by Cheapflights users on 8/3. 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 9/1511:55 pm -
1 stop9h 10m
Sun 9/205:05 pm -
2 stops9h 35m
Deal found 8/3![Southwest logo]()
$417
This Southwest deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1811:55 pm -
1 stop8h 00m
Mon 9/2112:50 pm -
1 stop9h 30m
Deal found 8/1![Southwest logo]()
$435
This Southwest deal was found by Cheapflights users on 7/30. 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 9/2711:55 pm -
1 stop9h 15m
Wed 9/306:15 pm -
1 stop7h 55m
Deal found 7/30![Southwest logo]()
$394
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 August 4, 2026.
Search for one-way flight options from Oakland to Chesapeake. Find affordable one-way fares based on user searches. Data last updated August 4, 2026.
This Southwest deal was found by Cheapflights users on 7/30. 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 9/711:55 pm -
1 stop9h 10m
Deal found 7/30![Southwest logo]()
$156
This Southwest deal was found by Cheapflights users on 8/2. 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 10/2211:55 pm -
1 stop8h 05m
Deal found 8/2![Southwest logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 9/78:37 pm -
3 stops46h 52m
Deal found 7/30![Multiple Airlines logo]()
$276
This Delta deal was found by Cheapflights users on 7/31. 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 8/156:00 am -
2 stops10h 41m
Deal found 7/31![Delta logo]()
$415
This Southwest deal was found by Cheapflights users on 8/3. 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 8/119:00 am -
1 stop8h 30m
Deal found 8/3![Southwest logo]()
$494
This Delta deal was found by Cheapflights users on 7/31. 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 8/116:00 am -
2 stops13h 01m
Deal found 7/31![Delta logo]()
$499
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1011:30 pm -
3 stops42h 09m
Deal found 7/31![Multiple Airlines logo]()
$513
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 8/1111:30 pm -
3 stops42h 09m
Deal found 8/4![Multiple Airlines logo]()
$521
This Delta deal was found by Cheapflights users on 7/30. 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.
Sun 9/1312:39 pm -
2 stops20h 16m
Deal found 7/30![Delta logo]()
$529
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 August 4, 2026.
Round-trip from | $347 (Southwest) |
|---|---|
One-way from | $156 (Southwest) |
Popular in | April |
Cheapest in | February |
Average price | $429 |
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 2,558,603 searches. Data last updated August 4, 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
Quickest round-trip
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Wed 10/14
11:55 pm-11:00 am
1 stop8h 05m
Norfolk
Mon 10/19
7:00 pm-12:10 am
1 stop8h 10m
$347
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Sun 9/27
11:55 pm-12:10 pm
1 stop9h 15m
Norfolk
Wed 9/30
6:15 pm-11:10 pm
1 stop7h 55m
$394
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Tue 9/15
11:55 pm-12:05 pm
1 stop9h 10m
Norfolk
Sun 9/20
5:05 pm-11:40 pm
2 stops9h 35m
$417
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Fri 9/18
11:55 pm-10:55 am
1 stop8h 00m
Norfolk
Mon 9/21
8:00 am-9:25 pm
2 stops16h 25m
$417
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Thu 10/22
5:25 am-5:10 pm
2 stops8h 45m
Norfolk
Sun 10/25
6:20 am-2:15 pm
2 stops10h 55m
$518
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Tue 9/1
11:55 pm-12:05 pm
1 stop9h 10m
Norfolk
Mon 9/7
6:45 pm-11:10 pm
1 stop7h 25m
$681
Cheapest one-way
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Mon 9/7
11:55 pm-12:05 pm
1 stop9h 10m
$156
Quickest one-way
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Thu 10/22
11:55 pm-11:00 am
1 stop8h 05m
$200
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Mon 9/7
8:37 pm-10:29 pm
3 stops46h 52m
$276
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Mon 8/10
11:55 pm-12:05 pm
1 stop9h 10m
$494
Showing 1-10 of 15 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
No data available for this route at this time. Please check back soon.
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 4, 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.
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Overall
8.0
Entertainment
7.5
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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Alternative routes for Oakland 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.
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Find flights from Oakland to Chesapeake, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Oakland and Chesapeake flights
Browse other Oakland and Chesapeake flight options. Last updated on August 4, 2026.
Other flights from Oakland
Browse through other flights departing from Oakland. Flights are based on user searches made on Cheapflights and were last updated on August 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Oakland to Chesapeake flights
Consider these flights traveling from Oakland to Chesapeake.
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 2,558,603 searches. Data last updated August 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$317 | Average$532 | FlexibilityNo cancel fee | On-time63% |