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Cabo San Lucas

$502+ Cheap flights from Chesapeake, VA to Cabo San Lucas, Mexico

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 4/11. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJD
Mar 10 — Mar 171
Tue 3/10
Tue 3/17
1 adult, Economy
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Cheap flight deals from Chesapeake to Cabo San Lucas

Cheapest flights from Chesapeake to Cabo San Lucas
Explore the most affordable flight options available from Chesapeake to Cabo San Lucas. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 8, 2026.

This American Airlines deal was found by Cheapflights users on 2/7. 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.
Sat 4/117:15 pm
ORF
-
SJD
1 stop18h 16m
American Airlines
Thu 4/1610:35 am
SJD
-
ORF
1 stop9h 21m
American Airlines
Deal found 2/7$502
This Kiwi.com deal was found by Cheapflights users on 2/7. 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 4/186:43 pm
ORF
-
SJD
2 stops39h 42m
Multiple Airlines
Sat 4/258:05 am
SJD
-
ORF
2 stops10h 10m
Multiple Airlines
Deal found 2/7$519
This SmartFares deal was found by Cheapflights users on 2/7. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/245:50 am
ORF
-
SJD
1 stop10h 24m
Aeromexico
Tue 3/312:19 pm
SJD
-
ORF
1 stop7h 04m
Aeromexico
Deal found 2/7$522
This Delta deal was found by Cheapflights users on 2/8. 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 3/317:29 pm
ORF
-
SJD
2 stops15h 11m
Delta
Tue 4/78:35 am
SJD
-
ORF
2 stops9h 16m
Delta
Deal found 2/8$527
This Mytrip deal was found by Cheapflights users on 2/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/246:45 am
ORF
-
SJD
3 stops35h 35m
Multiple Airlines
Tue 3/317:53 pm
SJD
-
ORF
3 stops22h 54m
Multiple Airlines
Deal found 2/7$530
This American Airlines deal was found by Cheapflights users on 2/7. 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 4/16:15 am
ORF
-
SJD
2 stops10h 33m
American Airlines
Wed 4/812:41 pm
SJD
-
ORF
2 stops16h 54m
American Airlines
Deal found 2/7$547
This American Airlines deal was found by Cheapflights users on 2/8. 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.
Sat 5/27:15 pm
ORF
-
SJD
1 stop18h 12m
American Airlines
Sat 5/912:53 pm
SJD
-
ORF
1 stop16h 42m
American Airlines
Deal found 2/8$567
This Aeromexico deal was found by Cheapflights users on 2/5. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/176:35 am
ORF
-
SJD
1 stop9h 34m
Aeromexico
Fri 2/201:45 pm
SJD
-
ORF
1 stop8h 29m
Aeromexico
Deal found 2/5$568
This American Airlines deal was found by Cheapflights users on 2/7. 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.
Sat 2/287:57 pm
ORF
-
SJD
1 stop19h 13m
American Airlines
Sat 3/72:10 pm
SJD
-
ORF
1 stop15h 13m
American Airlines
Deal found 2/7$574

Find flight deals from Chesapeake to Cabo San Lucas

Keep the following information in mind while searching for Chesapeake to Cabo San Lucas flight deals. Data was last updated February 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$502
(American Airlines)

Popular in

December

Cheapest in

November

Average price

$664
Provider with most accurate pricing for Norfolk-San José del Cabo Los Cabos flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-San José del Cabo Los Cabos flights.
Search Deals
From Chesapeake to Cabo San Lucas
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($1 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chesapeake to Cabo San Lucas 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 February 8, 2026.
Use the filters below to find and compare flights from Chesapeake to Cabo San Lucas that are best for you.

Fly from

Chesapeake

Fly to

Cabo San Lucas

Route

Depart

Return

Price

NorfolkSan José del Cabo

ORF - SJD

ORFSJD

Norfolk

Sat 4/11

7:15 pm-9:34 am

1 stop17h 19m

San José del Cabo Los Cabos

Thu 4/16

11:31 am-10:56 pm

1 stop8h 25m

$502

NorfolkSan José del Cabo

ORF - SJD

ORFSJD

Norfolk

Sat 4/18

6:43 pm-7:25 am

2 stops39h 42m

San José del Cabo Los Cabos

Sat 4/25

8:05 am-9:15 pm

2 stops10h 10m

$519

NorfolkSan José del Cabo

ORF - SJD

ORFSJD

Norfolk

Tue 3/24

8:33 am-5:43 pm

2 stops12h 10m

San José del Cabo Los Cabos

Tue 3/31

2:19 pm-12:23 am

1 stop7h 04m

$522

NorfolkSan José del Cabo

ORF - SJD

ORFSJD

Norfolk

Wed 4/1

8:33 am-1:14 pm

1 stop7h 41m

San José del Cabo Los Cabos

Wed 4/8

10:49 am-11:33 pm

1 stop9h 44m

$522

NorfolkSan José del Cabo

ORF - SJD

ORFSJD

Norfolk

Tue 3/31

5:50 am-11:30 am

1 stop8h 40m

San José del Cabo Los Cabos

Tue 4/7

12:35 pm-10:20 pm

1 stop6h 45m

$522

NorfolkSan José del Cabo

ORF - SJD

ORFSJD

Norfolk

Tue 3/31

7:29 pm-7:40 am

2 stops15h 11m

San José del Cabo Los Cabos

Tue 4/7

8:35 am-8:51 pm

2 stops9h 16m

$527

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/6

Best time to book a flight from Chesapeake to Cabo San Lucas

Have a flexible travel schedule? Discover the best time to fly to Cabo San Lucas from Chesapeake with our price prediction graph.
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 Chesapeake to Cabo San Lucas

What is the cheapest month to book a flight from Chesapeake to Cabo San Lucas?

Currently, July is the cheapest month in which you can book a flight from Chesapeake to Cabo San Lucas (average of $409). Flying from Chesapeake to Cabo San Lucas in May is currently the most expensive (average of $607). 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 Cabo San Lucas

Get insights into the airlines that provide service to Cabo San Lucas. 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 Cabo San Lucas. Reviews last updated February 8, 2026.
Get a feel of what it's like to fly with Delta, United Airlines, and American Airlines from Chesapeake to Cabo San Lucas by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,173 reviews

Comfort

7.9

Entertainment

7.8

Overall

7.9

Food

7.2

Crew

8.5

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,173 reviews
Delta
7.9
Good
8,173 reviews

Comfort

7.9

Entertainment

7.8

Overall

7.9

Food

7.2

Crew

8.5

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,257 reviews
Delta
7.9
Good
8,173 reviews

Comfort

7.9

Entertainment

7.8

Overall

7.9

Food

7.2

Crew

8.5

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,255 reviews
Delta
7.9
Good
8,173 reviews

Comfort

7.9

Entertainment

7.8

Overall

7.9

Food

7.2

Crew

8.5

Boarding

8.1

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Chesapeake to Cabo San Lucas. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chesapeake to Cabo San Lucas?

    Departing from Chesapeake to Cabo San Lucas will take you 12h 10m. Airlines will cover a distance of 2202 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from Chesapeake to Cabo San Lucas that include hotel bookings?

    Yes. In addition to deals on Chesapeake to Cabo San Lucas flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chesapeake to Cabo San Lucas?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chesapeake to Cabo San Lucas.

  • Can I find deals for business class flights from Chesapeake to Cabo San Lucas?

    Yes. Cheapflights offers flight deals from Chesapeake to Cabo San Lucas by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chesapeake to Cabo San Lucas?

    Currently, July is the cheapest month in which you can book a flight from Chesapeake to Cabo San Lucas (average of $409). Flying from Chesapeake to Cabo San Lucas in May is currently the most expensive (average of $607). 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 4 airlines flying from Chesapeake to Cabo San Lucas

Discover the top 4 airlines that operate flights from Chesapeake to Cabo San Lucas. 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 February 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
AeromexicoCheapest$317Average$605FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$409Average$644FlexibilityNo cancel feeOn-time71%
DeltaCheapest$487Average$684FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$561Average$719FlexibilityNo cancel feeOn-time69%

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