$160+ 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 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — RIC
Apr 17 — Apr 241
Round-trip
1 adult, Economy
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Find cheap flights from Oakland 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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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 March 18, 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 March 18, 2026.
This Southwest deal was found by Cheapflights users on 3/13. 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 6/241:10 pm
OAK
- ORF
2 stops8h 35m
Southwest
Thu 6/257:15 pm
ORF
- OAK
1 stop7h 55m
Southwest
Deal found 3/13![Southwest logo]()
$414
This Southwest deal was found by Cheapflights users on 3/14. 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 8/1111:55 pm
OAK
- ORF
1 stop9h 10m
Southwest
Sat 8/156:00 am
ORF
- OAK
1 stop10h 55m
Southwest
Deal found 3/14![Southwest logo]()
$419
This Southwest deal was found by Cheapflights users on 3/15. 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.
Sat 8/17:40 pm
OAK
- ORF
2 stops10h 50m
Southwest
Sat 8/811:35 am
ORF
- OAK
2 stops10h 35m
Southwest
Deal found 3/15![Southwest logo]()
$424
This Southwest deal was found by Cheapflights users on 3/17. 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 5/295:55 am
OAK
- ORF
1 stop13h 05m
Southwest
Thu 6/47:15 pm
ORF
- OAK
1 stop7h 55m
Southwest
Deal found 3/17![Southwest logo]()
$439
This Southwest deal was found by Cheapflights users on 3/16. 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.
Mon 5/1111:55 pm
OAK
- ORF
2 stops9h 00m
Southwest
Thu 5/145:25 pm
ORF
- OAK
2 stops10h 00m
Southwest
Deal found 3/16![Southwest logo]()
$444
This Southwest deal was found by Cheapflights users on 3/15. 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 5/195:50 am
OAK
- ORF
2 stops9h 00m
Southwest
Sun 5/244:45 pm
ORF
- OAK
2 stops10h 10m
Southwest
Deal found 3/15![Southwest logo]()
$486
This Delta deal was found by Cheapflights users on 3/17. 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.
Thu 5/286:00 am
OAK
- ORF
2 stops14h 15m
Delta
Wed 6/34:58 pm
ORF
- OAK
2 stops9h 59m
Delta
Deal found 3/17![Delta logo]()
$493
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 March 18, 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 March 18, 2026.
This Southwest deal was found by Cheapflights users on 3/16. 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.
Mon 5/1111:55 pm
OAK
- ORF
2 stops9h 00m
Southwest
Thu 5/145:25 pm
ORF
- OAK
2 stops10h 00m
Southwest
Deal found 3/16![Southwest logo]()
$444
This Delta deal was found by Cheapflights users on 3/17. 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.
Thu 5/286:00 am
OAK
- ORF
2 stops14h 15m
Delta
Wed 6/34:58 pm
ORF
- OAK
2 stops9h 59m
Delta
Deal found 3/17![Delta logo]()
$493
This Southwest deal was found by Cheapflights users on 3/15. 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 5/195:50 am
OAK
- ORF
2 stops9h 00m
Southwest
Sun 5/244:45 pm
ORF
- OAK
2 stops10h 10m
Southwest
Deal found 3/15![Southwest logo]()
$486
This Delta deal was found by Cheapflights users on 3/17. 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.
Thu 4/235:04 pm
OAK
- ORF
2 stops21h 13m
Delta
Tue 4/282:03 pm
ORF
- OAK
2 stops12h 51m
Delta
Deal found 3/17![Delta logo]()
$577
This Southwest deal was found by Cheapflights users on 3/18. 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.
Sun 4/1211:55 pm
OAK
- ORF
2 stops9h 20m
Southwest
Sat 4/181:15 pm
ORF
- OAK
2 stops11h 30m
Southwest
Deal found 3/18![Southwest logo]()
$558
This Delta deal was found by Cheapflights users on 3/16. 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.
Tue 6/95:05 pm
OAK
- ORF
2 stops27h 28m
Delta
Mon 6/155:50 am
ORF
- OAK
2 stops20h 59m
Delta
Deal found 3/16![Delta logo]()
$723
This Delta deal was found by Cheapflights users on 3/16. 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.
Mon 6/85:55 am
OAK
- ORF
2 stops26h 34m
Delta
Mon 6/155:00 pm
ORF
- OAK
2 stops26h 31m
Delta
Deal found 3/16![Delta logo]()
$746
This Southwest deal was found by Cheapflights users on 3/18. 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 3/2510:20 am
OAK
- ORF
2 stops9h 15m
Southwest
Thu 3/267:20 pm
ORF
- OAK
1 stop7h 50m
Southwest
Deal found 3/18![Southwest logo]()
$777
This Delta deal was found by Cheapflights users on 3/17. 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 4/245:55 am
OAK
- ORF
2 stops14h 00m
Delta
Wed 4/295:45 am
ORF
- OAK
2 stops9h 08m
Delta
Deal found 3/17![Delta logo]()
$746
This Delta deal was found by Cheapflights users on 3/16. 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.
Wed 6/101:15 pm
OAK
- ORF
2 stops31h 18m
Delta
Fri 6/195:50 am
ORF
- OAK
2 stops20h 59m
Delta
Deal found 3/16![Delta logo]()
$768
Last-minute flights from Oakland to ChesapeakeDiscover last-minute flight deals from Oakland to Chesapeake. Data last updated March 18, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Chesapeake. Data last updated March 18, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 3/18. 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 3/2510:20 am
OAK
- ORF
2 stops9h 15m
Southwest
Thu 3/267:20 pm
ORF
- OAK
1 stop7h 50m
Southwest
Deal found 3/18![Southwest logo]()
$777
This Southwest deal was found by Cheapflights users on 3/18. 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.
Thu 4/210:50 am
OAK
- ORF
2 stops9h 45m
Southwest
Mon 4/67:20 pm
ORF
- OAK
1 stop7h 50m
Southwest
Deal found 3/18![Southwest logo]()
$592
This Southwest deal was found by Cheapflights users on 3/18. 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.
Sun 4/1211:55 pm
OAK
- ORF
2 stops9h 20m
Southwest
Sat 4/181:15 pm
ORF
- OAK
2 stops11h 30m
Southwest
Deal found 3/18![Southwest logo]()
$558
This Delta deal was found by Cheapflights users on 3/17. 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.
Thu 4/235:04 pm
OAK
- ORF
2 stops21h 13m
Delta
Wed 4/295:45 am
ORF
- OAK
2 stops9h 08m
Delta
Deal found 3/17![Delta logo]()
$547
This Delta deal was found by Cheapflights users on 3/17. 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.
Thu 4/235:04 pm
OAK
- ORF
2 stops21h 13m
Delta
Tue 4/282:03 pm
ORF
- OAK
2 stops12h 51m
Delta
Deal found 3/17![Delta logo]()
$577
This Delta deal was found by Cheapflights users on 3/17. 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 4/245:55 am
OAK
- ORF
2 stops14h 00m
Delta
Wed 4/295:45 am
ORF
- OAK
2 stops9h 08m
Delta
Deal found 3/17![Delta logo]()
$746
This Delta deal was found by Cheapflights users on 3/17. 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 4/245:55 am
OAK
- ORF
2 stops14h 00m
Delta
Tue 4/282:03 pm
ORF
- OAK
2 stops12h 51m
Delta
Deal found 3/17![Delta logo]()
$776
This Southwest deal was found by Cheapflights users on 3/17. 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.
Thu 4/307:30 pm
OAK
- ORF
2 stops10h 55m
Southwest
Sun 5/310:20 am
ORF
- OAK
1 stop13h 25m
Southwest
Deal found 3/17![Southwest logo]()
$569
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 March 18, 2026.
Search for one-way flight options from Oakland to Chesapeake. Find affordable one-way fares based on user searches. Data last updated March 18, 2026.
This Southwest deal was found by Cheapflights users on 3/15. 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.
Sat 5/25:05 am
OAK
- ORF
2 stops8h 35m
Southwest
Deal found 3/15![Southwest logo]()
$160
This Southwest deal was found by Cheapflights users on 3/17. 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.
Mon 5/1111:55 pm
OAK
- ORF
2 stops9h 00m
Southwest
Deal found 3/17![Southwest logo]()
$183
This Southwest deal was found by Cheapflights users on 3/16. 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.
Thu 5/2810:25 am
OAK
- ORF
2 stops9h 30m
Southwest
Deal found 3/16![Southwest logo]()
$193
This Southwest deal was found by Cheapflights users on 3/13. 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 6/241:10 pm
OAK
- ORF
2 stops8h 35m
Southwest
Deal found 3/13![Southwest logo]()
$210
This Southwest deal was found by Cheapflights users on 3/17. 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.
Sun 5/106:05 am
OAK
- ORF
2 stops10h 55m
Southwest
Deal found 3/17![Southwest logo]()
$235
This Southwest deal was found by Cheapflights users on 3/16. 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.
Mon 4/135:55 am
OAK
- ORF
1 stop13h 05m
Southwest
Deal found 3/16![Southwest logo]()
$326
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 March 18, 2026.
Round-trip from | $385 (Southwest) |
|---|---|
One-way from | $160 (Southwest) |
Popular in | May |
Cheapest in | February |
Average price | $518 |
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 March 18, 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 - ORF
OAKORF
Oakland
Mon 5/11
11:55 pm-11:55 am
2 stops9h 00m
Norfolk
Thu 5/14
5:25 pm-12:25 am
2 stops10h 00m
$444
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Tue 5/19
5:50 am-5:50 pm
2 stops9h 00m
Norfolk
Sun 5/24
4:45 pm-11:55 pm
2 stops10h 10m
$486
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Thu 5/28
6:00 am-11:15 pm
2 stops14h 15m
Norfolk
Wed 6/3
4:58 pm-11:57 pm
2 stops9h 59m
$493
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Sun 4/12
11:55 pm-12:15 pm
2 stops9h 20m
Norfolk
Sat 4/18
1:15 pm-9:45 pm
2 stops11h 30m
$558
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Thu 4/23
5:04 pm-5:17 pm
2 stops21h 13m
Norfolk
Tue 4/28
2:03 pm-11:54 pm
2 stops12h 51m
$577
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Tue 6/9
5:05 pm-11:33 pm
2 stops27h 28m
Norfolk
Mon 6/15
5:50 am-11:49 pm
2 stops20h 59m
$723
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Mon 6/8
5:55 am-11:29 am
2 stops26h 34m
Norfolk
Mon 6/15
5:00 pm-4:31 pm
2 stops26h 31m
$746
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Fri 4/24
5:55 am-10:55 pm
2 stops14h 00m
Norfolk
Wed 4/29
5:45 am-11:53 am
2 stops9h 08m
$746
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Wed 6/10
1:15 pm-11:33 pm
2 stops31h 18m
Norfolk
Fri 6/19
5:50 am-11:49 pm
2 stops20h 59m
$768
Quickest round-trip
OaklandNorfolk
OAK - ORF
OAKORF
Oakland
Wed 3/25
10:20 am-10:35 pm
2 stops9h 15m
Norfolk
Thu 3/26
7:20 pm-12:10 am
1 stop7h 50m
$777
Showing 1-10 of 17 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
What is the cheapest month to book a flight from Oakland, California to Chesapeake?
Currently, August is the cheapest month in which you can book a flight from Oakland, California to Chesapeake (average of $91). Flying from Oakland, California to Chesapeake in December is currently the most expensive (average of $272). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
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 March 18, 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
Crew
8.6
Comfort
8.0
Overall
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Entertainment
7.5
Crew
8.6
Comfort
8.0
Overall
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
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
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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 March 18, 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 March 18, 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 2 airlines flying from Oakland to Chesapeake
Discover the top 2 airlines 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 March 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$283 | Average$473 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$326 | Average$361 | FlexibilityNo cancel fee | On-timeN/A |