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$246+ 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 2/1. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — HNL
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
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 December 28, 2025.

This United Airlines deal was found by Cheapflights users on 12/28. 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.
Mon 12/296:20 amORF - HNL
1 stop12h 52mUnited Airlines
Sun 1/113:55 pmHNL - ORF
1 stop14h 49mUnited Airlines
Deal found 12/28$1,093
This Delta deal was found by Cheapflights users on 12/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:23 amORF - HNL
1 stop13h 41mDelta
Sun 1/115:15 pmHNL - ORF
2 stops15h 42mDelta
Deal found 12/28$1,098
This United Airlines deal was found by Cheapflights users on 12/26. 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 12/306:20 amORF - LIH
2 stops15h 44mUnited Airlines
Thu 1/18:30 pmLIH - ORF
2 stops20h 57mUnited Airlines
Deal found 12/26$1,131
This Delta deal was found by Cheapflights users on 12/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:23 amORF - HNL
2 stops20h 19mDelta
Wed 12/316:50 pmHNL - ORF
1 stop11h 27mDelta
Deal found 12/28$1,152
This Southwest deal was found by Cheapflights users on 12/28. 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.
Mon 12/298:05 pmORF - HNL
2 stops22h 55mSouthwest
Wed 12/319:25 pmHNL - ORF
2 stops15h 10mSouthwest
Deal found 12/28$1,219
This United Airlines deal was found by Cheapflights users on 12/28. 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.
Mon 12/296:20 amORF - HNL
1 stop12h 52mUnited Airlines
Wed 12/313:56 pmHNL - ORF
1 stop14h 03mUnited Airlines
Deal found 12/28$1,253
This Delta deal was found by Cheapflights users on 12/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:23 amORF - HNL
1 stop15h 37mDelta
Tue 1/65:15 pmHNL - ORF
2 stops13h 55mDelta
Deal found 12/26$1,258
This Southwest deal was found by Cheapflights users on 12/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/308:05 pmORF - HNL
2 stops22h 15mSouthwest
Thu 1/19:25 pmHNL - ORF
2 stops17h 40mSouthwest
Deal found 12/26$1,344
This United Airlines deal was found by Cheapflights users on 12/26. 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 12/306:30 amORF - HNL
2 stops33h 50mUnited Airlines
Thu 1/110:50 pmHNL - ORF
1 stop19h 09mUnited Airlines
Deal found 12/26$1,376

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 December 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$575
(Kiwi.com)

One-way from

$246
(Kiwi.com)

Popular in

December

Cheapest in

November

Average price

$1,223
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
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($26 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 28, 2025.
Use the filters below to find and compare flights from Chesapeake to Hawaii that are best for you.

Fly from

Chesapeake

Fly to

Hawaii

Route

Depart

Return

Price

NorfolkKailua-Kona

ORF - KOA

ORFKOA

Norfolk

Mon 2/2

7:45 am-7:57 pm

2 stops17h 12m

Kona Intl

Mon 2/9

9:55 pm-5:05 pm

2 stops14h 10m

$587

NorfolkLihue

ORF - LIH

ORFLIH

Norfolk

Mon 1/26

6:20 am-7:55 pm

2 stops18h 35m

Lihue

Mon 2/2

9:20 pm-5:34 pm

2 stops15h 14m

$587

NorfolkLihue

ORF - LIH

ORFLIH

Norfolk

Mon 2/2

5:20 am-7:54 pm

2 stops19h 34m

Lihue

Mon 2/9

9:20 pm-5:05 pm

2 stops14h 45m

$608

NorfolkKahului

ORF - OGG

ORFOGG

Norfolk

Mon 1/19

5:35 am-6:04 pm

2 stops17h 29m

Kahului

Wed 1/28

10:00 pm-5:06 pm

2 stops14h 06m

$633

NorfolkHonolulu

ORF - HNL

ORFHNL

Norfolk

Tue 2/3

7:01 am-9:28 pm

2 stops19h 27m

Honolulu

Thu 2/5

8:00 am-9:10 am

2 stops20h 10m

$644

NorfolkHonolulu

ORF - HNL

ORFHNL

Norfolk

Thu 1/29

7:01 am-9:28 pm

2 stops19h 27m

Honolulu

Tue 2/3

9:35 pm-12:16 am

2 stops21h 41m

$644

NorfolkHonolulu

ORF - HNL

ORFHNL

Norfolk

Tue 2/3

7:01 am-11:55 am

2 stops33h 54m

Honolulu

Fri 2/6

9:35 pm-8:44 pm

2 stops18h 09m

$655

NorfolkHonolulu

ORF - HNL

ORFHNL

Norfolk

Mon 2/2

3:37 pm-11:55 am

2 stops25h 18m

Honolulu

Thu 2/5

8:00 am-9:10 am

2 stops20h 10m

$658

NorfolkHonolulu

ORF - HNL

ORFHNL

Norfolk

Wed 2/4

6:20 am-9:28 pm

2 stops20h 08m

Honolulu

Fri 2/6

9:35 pm-9:30 pm

2 stops18h 55m

$661

NorfolkKahului

ORF - OGG

ORFOGG

Norfolk

Sun 1/25

7:33 pm-12:29 pm

2 stops45h 56m

Kahului

Sun 2/1

11:55 am-8:38 pm

1 stop27h 43m

$665

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/27

Showing 1-10 of 52 results
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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

What is the cheapest month to book a flight from Chesapeake to Hawaii?

Currently, November is the cheapest month in which you can book a flight from Chesapeake to Hawaii (average of $298). Flying from Chesapeake to Hawaii in December is currently the most expensive (average of $617). 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 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 December 28, 2025.
See what other customers who have flown with Southwest, Delta, and United 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
4,252 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,252 reviews
Southwest
8.0
Very good
4,252 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,014 reviews
Southwest
8.0
Very good
4,252 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,120 reviews
Southwest
8.0
Very good
4,252 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,072 reviews
Southwest
8.0
Very good
4,252 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 14h 04m. Delta provides one of the quickest options available for as low as $728. The distance between Chesapeake and Hawaii is about 4954 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 - Kahului or Norfolk - Kona Intl, 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.

  • What is the cheapest month to book a flight from Chesapeake to Hawaii?

    Currently, November is the cheapest month in which you can book a flight from Chesapeake to Hawaii (average of $298). Flying from Chesapeake to Hawaii in December is currently the most expensive (average of $617). 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

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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 December 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$387Average$947FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$492Average$1,007FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$518Average$1,016FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$733Average$861FlexibilityNo cancel feeOn-time63%

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