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$368+ Cheap flights from Chesapeake, VA to Hawaii

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 6/29. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — HNL
Jun 29 — Jul 61
Mon 6/29
Mon 7/6
1 adult, Economy
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Cheap flight deals from Chesapeake to Hawaii

Cheapest flights from Chesapeake to Hawaii
Explore the most affordable flight options available from Chesapeake to Hawaii. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 30, 2026.

This Southwest deal was found by Cheapflights users on 5/28. 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 8/196:15 am
ORF
-
HNL
2 stops21h 00m
Southwest
Wed 8/269:55 pm
HNL
-
ORF
2 stops17h 40m
Southwest
Deal found 5/28$487
This Delta deal was found by Cheapflights users on 5/25. 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 8/196:04 am
ORF
-
HNL
1 stop14h 03m
Delta
Wed 8/263:50 pm
HNL
-
ORF
1 stop13h 35m
Delta
Deal found 5/25$582
This United Airlines deal was found by Cheapflights users on 5/26. 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 9/158:05 am
ORF
-
HNL
1 stop13h 11m
United Airlines
Thu 9/242:00 pm
HNL
-
ORF
2 stops16h 15m
United Airlines
Deal found 5/26$588
This American Airlines deal was found by Cheapflights users on 5/25. 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.
Tue 8/257:03 am
ORF
-
OGG
1 stop12h 51m
American Airlines
Tue 9/15:55 pm
OGG
-
ORF
2 stops15h 22m
American Airlines
Deal found 5/25$588
This Delta deal was found by Cheapflights users on 5/29. 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 9/166:40 am
ORF
-
OGG
2 stops17h 12m
Delta
Thu 9/249:15 pm
OGG
-
ORF
2 stops16h 47m
Delta
Deal found 5/29$595
This Delta deal was found by Cheapflights users on 5/29. 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 9/157:09 am
ORF
-
HNL
1 stop13h 43m
Delta
Tue 9/223:55 pm
HNL
-
ORF
1 stop13h 28m
Delta
Deal found 5/29$602
This United Airlines deal was found by Cheapflights users on 5/28. 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 8/196:02 am
ORF
-
HNL
1 stop13h 26m
United Airlines
Wed 8/261:25 pm
HNL
-
ORF
2 stops14h 09m
United Airlines
Deal found 5/28$608
This American Airlines deal was found by Cheapflights users on 5/29. 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.
Tue 9/1510:24 am
ORF
-
HNL
2 stops15h 52m
American Airlines
Tue 9/228:40 pm
HNL
-
ORF
2 stops15h 23m
American Airlines
Deal found 5/29$613
This Southwest deal was found by Cheapflights users on 5/29. 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 8/1710:15 am
ORF
-
HNL
2 stops17h 00m
Southwest
Mon 8/319:55 pm
HNL
-
ORF
2 stops16h 55m
Southwest
Deal found 5/29$621
This United Airlines deal was found by Cheapflights users on 5/29. 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 9/168:05 am
ORF
-
OGG
1 stop13h 00m
United Airlines
Thu 9/241:52 pm
OGG
-
ORF
2 stops16h 23m
United Airlines
Deal found 5/29$639
This Delta deal was found by Cheapflights users on 5/29. 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 8/187:17 am
ORF
-
HNL
1 stop12h 34m
Delta
Tue 9/17:00 am
HNL
-
ORF
2 stops20h 13m
Delta
Deal found 5/29$640
This United Airlines deal was found by Cheapflights users on 5/29. 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 9/228:05 am
ORF
-
OGG
1 stop13h 00m
United Airlines
Wed 9/237:00 am
OGG
-
ORF
2 stops23h 15m
United Airlines
Deal found 5/29$642

Find flight deals from Chesapeake to Hawaii

Keep the following information in mind while searching for Chesapeake to Hawaii flight deals. Data was last updated May 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$487
(Southwest)

One-way from

$368
(American Airlines)

Popular in

July

Cheapest in

November

Average price

$827
Provider with most accurate pricing for Norfolk-Honolulu flight deals.
Search Deals
Provider most trusted by Cheapflights users for Norfolk-Honolulu flights.
Search Deals
From Chesapeake to Hawaii
Search Deals
One-way flight from Chesapeake to Hawaii
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($107 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chesapeake to Hawaii 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 30, 2026.
Use the filters below to find and compare flights from Chesapeake to Hawaii that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

NorfolkHonolulu

ORF - HNL

ORFHNL

Norfolk

Wed 8/19

6:10 am-1:34 pm

1 stop13h 24m

Honolulu

Wed 8/26

1:00 pm-9:34 am

2 stops14h 34m

$588

NorfolkKahului

ORF - OGG

ORFOGG

Norfolk

Tue 8/25

7:03 am-1:54 pm

1 stop12h 51m

Kahului

Tue 9/1

5:55 pm-3:17 pm

2 stops15h 22m

$588

NorfolkKahului

ORF - OGG

ORFOGG

Norfolk

Tue 9/22

6:15 am-3:05 pm

2 stops14h 50m

Kahului

Tue 9/29

12:05 pm-9:45 am

2 stops15h 40m

$593

NorfolkKahului

ORF - OGG

ORFOGG

Norfolk

Wed 9/16

8:05 am-3:05 pm

1 stop13h 00m

Kahului

Thu 9/24

1:52 pm-12:15 pm

2 stops16h 23m

$639

NorfolkKahului

ORF - OGG

ORFOGG

Norfolk

Tue 9/22

8:05 am-3:05 pm

1 stop13h 00m

Kahului

Wed 9/23

7:00 am-12:15 pm

2 stops23h 15m

$642

NorfolkHonolulu

ORF - HNL

ORFHNL

Norfolk

Mon 9/14

6:05 am-2:01 pm

1 stop13h 56m

Honolulu

Mon 9/21

10:39 pm-10:11 pm

2 stops17h 32m

$675

NorfolkLihue

ORF - LIH

ORFLIH

Norfolk

Tue 9/22

8:05 am-3:40 pm

1 stop13h 35m

Lihue

Wed 9/23

1:03 pm-9:45 am

2 stops14h 42m

$675

NorfolkHonolulu

ORF - HNL

ORFHNL

Norfolk

Mon 8/31

7:17 am-1:51 pm

1 stop12h 34m

Honolulu

Sun 9/27

10:39 pm-8:02 pm

2 stops15h 23m

$707

NorfolkKahului

ORF - OGG

ORFOGG

Norfolk

Sun 11/1

8:00 am-4:37 pm

1 stop13h 37m

Kahului

Sun 11/8

3:01 pm-10:46 am

2 stops14h 45m

$713

NorfolkKailua-Kona

ORF - KOA

ORFKOA

Norfolk

Sun 11/1

5:50 am-6:54 pm

2 stops18h 04m

Kona Intl

Sun 11/8

8:40 pm-10:50 pm

2 stops21h 10m

$738

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/26

Showing 1-10 of 46 resultsSorted by cheapest first
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5

Best time to book a flight from Chesapeake to Hawaii

Have a flexible travel schedule? Discover the best time to fly to Hawaii 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 Hawaii

How much does it cost to fly round-trip from Chesapeake to Hawaii?

Reviews of airlines servicing Hawaii

Get insights into the airlines that provide service to Hawaii. 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 Hawaii. Reviews last updated May 30, 2026.
See what other customers who have flown with Southwest,Delta, andUnited Airlines from Chesapeake to Hawaii have to say. 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.
Southwest
8.0
Very good
4,262 reviews

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Walter,May 2026

LAS - BUR

Short but excellent flight. Everyone was friendly and professional it was a great flight!
Southwest
8.0
Very good
4,262 reviews
Southwest
8.0
Very good
4,262 reviews

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Walter,May 2026

LAS - BUR

Short but excellent flight. Everyone was friendly and professional it was a great flight!
Delta
7.9
Good
8,417 reviews
Southwest
8.0
Very good
4,262 reviews

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Walter,May 2026

LAS - BUR

Short but excellent flight. Everyone was friendly and professional it was a great flight!
United Airlines
7.4
Good
9,766 reviews
Southwest
8.0
Very good
4,262 reviews

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Walter,May 2026

LAS - BUR

Short but excellent flight. Everyone was friendly and professional it was a great flight!
American Airlines
7.1
Good
11,640 reviews
Southwest
8.0
Very good
4,262 reviews

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Walter,May 2026

LAS - BUR

Short but excellent flight. Everyone was friendly and professional it was a great flight!

Related info for your journey

Find useful and relevant information for your journey from Chesapeake to Hawaii. 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 Hawaii?

    A quick flight from Chesapeake to Hawaii can take about 12h 51m. United Airlines provides one of the quickest options available for as low as $588. The distance between Chesapeake and Hawaii is about 4838 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Chesapeake to Hawaii one-way?

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as $225. However, be on the lookout for offers from American Airlines and United Airlines, as they are both options that can get you from Chesapeake to Hawaii for a low price.

  • What are the most popular routes from Chesapeake to Hawaii?

    While some choose either Norfolk - Kona Intl or Norfolk - Kahului, Norfolk - Honolulu is the most popular route from Chesapeake to Hawaii.

  • Can I find deals for flights from Chesapeake to Hawaii that include hotel bookings?

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

  • How can I find direct flights from Chesapeake to Hawaii?

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

  • Can I find deals for business class flights from Chesapeake to Hawaii?

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

See more FAQs

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Top 4 airlines flying from Chesapeake to Hawaii

Discover the top 4 airlines that operate flights from Chesapeake to Hawaii. 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 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$381Average$954FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$492Average$949FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$518Average$1,100FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$701Average$839FlexibilityNo cancel feeOn-time63%

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