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$243+ 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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — HNL
Feb 5 — Feb 121
Thu 2/5
Thu 2/12
1 adult, Economy
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Cheap flight deals from Chesapeake to Hawaii

Keep the following information in mind while searching for Chesapeake to Hawaii flight deals. Data was last updated January 6, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$404
(Southwest)

One-way from

$243
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$828
Provider with most accurate pricing for Norfolk-Honolulu flight deals.
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Provider most trusted by Cheapflights users for Norfolk-Honolulu flights.
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From Chesapeake to Hawaii
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One-way flight from Chesapeake to Hawaii
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Highest demand for flights based on searches. 13% potential increase in price ($138 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($22 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find 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 January 6, 2026.

This Southwest deal was found by Cheapflights users on 1/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/278:50 amORF - HNL
2 stops17h 10mSouthwest
Tue 2/31:30 pmHNL - ORF
2 stops15h 10mSouthwest
Deal found 1/5$404
This Delta deal was found by Cheapflights users on 1/6. 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 2/26:20 amORF - LIH
2 stops18h 34mDelta
Mon 2/910:39 pmLIH - ORF
2 stops19h 23mDelta
Deal found 1/6$485
This Delta deal was found by Cheapflights users on 1/6. 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 2/246:35 amORF - HNL
2 stops19h 53mDelta
Tue 3/108:39 pmHNL - ORF
2 stops17h 49mDelta
Deal found 1/6$495
This Delta deal was found by Cheapflights users on 1/6. 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 2/26:20 amORF - KOA
2 stops18h 37mDelta
Mon 2/910:55 pmKOA - ORF
2 stops19h 07mDelta
Deal found 1/6$503
This Delta deal was found by Cheapflights users on 1/6. 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 1/276:20 amORF - HNL
2 stops20h 08mDelta
Tue 2/31:55 pmHNL - ORF
2 stops14h 15mDelta
Deal found 1/6$515
This Delta deal was found by Cheapflights users on 1/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/276:20 amORF - HNL
2 stops20h 08mDelta
Tue 3/34:50 pmHNL - ORF
1 stop13h 40mDelta
Deal found 1/5$524
This United Airlines deal was found by Cheapflights users on 1/6. 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 1/278:00 amORF - HNL
1 stop13h 43mUnited Airlines
Tue 2/36:05 pmHNL - ORF
2 stops15h 02mUnited Airlines
Deal found 1/6$530
This Delta deal was found by Cheapflights users on 1/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/275:35 amORF - HNL
2 stops16h 30mDelta
Wed 2/49:35 pmHNL - ORF
2 stops14h 31mDelta
Deal found 1/5$535
This Kiwi.com deal was found by Cheapflights users on 1/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/259:33 amORF - HNL
1 stop30h 27mMultiple Airlines
Mon 2/27:40 amHNL - ORF
2 stops29h 58mMultiple Airlines
Deal found 1/5$541
This Kiwi.com deal was found by Cheapflights users on 1/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/259:33 amORF - HNL
1 stop30h 27mMultiple Airlines
Tue 2/39:38 pmHNL - ORF
2 stops41h 46mMultiple Airlines
Deal found 1/5$567
This American Airlines deal was found by Cheapflights users on 1/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/26:00 amORF - LIH
2 stops15h 37mAmerican Airlines
Mon 2/910:10 pmLIH - ORF
2 stops16h 47mAmerican Airlines
Deal found 1/5$569
This Kiwi.com deal was found by Cheapflights users on 1/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/259:33 amORF - HNL
1 stop30h 27mMultiple Airlines
Wed 2/410:03 amHNL - ORF
1 stop29h 21mMultiple Airlines
Deal found 1/5$573

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 January 6, 2026.
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

NorfolkLihue

ORF - LIH

ORFLIH

Norfolk

Mon 2/2

6:20 am-7:54 pm

2 stops18h 34m

Lihue

Mon 2/9

10:39 pm-11:02 pm

2 stops19h 23m

$485

NorfolkKailua-Kona

ORF - KOA

ORFKOA

Norfolk

Mon 2/2

6:20 am-7:57 pm

2 stops18h 37m

Kona Intl

Mon 2/9

10:55 pm-11:02 pm

2 stops19h 07m

$503

NorfolkHonolulu

ORF - HNL

ORFHNL

Norfolk

Tue 1/27

8:00 am-4:43 pm

1 stop13h 43m

Honolulu

Mon 2/2

5:00 pm-9:52 am

1 stop11h 52m

$524

NorfolkHonolulu

ORF - HNL

ORFHNL

Norfolk

Thu 2/5

8:00 am-4:43 pm

1 stop13h 43m

Honolulu

Mon 2/9

5:00 pm-9:52 am

1 stop11h 52m

$524

NorfolkHonolulu

ORF - HNL

ORFHNL

Norfolk

Thu 2/19

6:20 am-2:23 pm

1 stop13h 03m

Honolulu

Tue 2/24

5:00 pm-9:48 am

1 stop11h 48m

$524

NorfolkHonolulu

ORF - HNL

ORFHNL

Norfolk

Tue 1/27

6:20 am-3:10 pm

1 stop13h 50m

Honolulu

Tue 3/3

4:50 pm-11:30 am

1 stop13h 40m

$524

NorfolkHonolulu

ORF - HNL

ORFHNL

Norfolk

Tue 2/17

6:00 am-3:28 pm

1 stop14h 28m

Honolulu

Tue 2/24

5:00 pm-9:48 am

1 stop11h 48m

$524

NorfolkHonolulu

ORF - HNL

ORFHNL

Norfolk

Tue 2/3

8:00 am-4:43 pm

1 stop13h 43m

Honolulu

Tue 2/10

5:00 pm-9:52 am

1 stop11h 52m

$524

NorfolkHonolulu

ORF - HNL

ORFHNL

Norfolk

Tue 2/17

6:35 am-9:28 pm

2 stops19h 53m

Honolulu

Tue 2/24

1:55 pm-11:30 am

2 stops16h 35m

$529

NorfolkLihue

ORF - LIH

ORFLIH

Norfolk

Mon 2/2

6:00 am-4:37 pm

2 stops15h 37m

Lihue

Mon 2/9

10:10 pm-7:57 pm

2 stops16h 47m

$569

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/5

Showing 1-10 of 50 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 $592). 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 January 6, 2026.
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
4,249 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

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
4,249 reviews
Southwest
8.0
Very good
4,249 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

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
8,022 reviews
Southwest
8.0
Very good
4,249 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

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
9,138 reviews
Southwest
8.0
Very good
4,249 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

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
11,088 reviews
Southwest
8.0
Very good
4,249 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

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. Southwest provides one of the quickest options available for as low as $530. The distance between Chesapeake and Hawaii is about 4902 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 $592). 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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Alternative routes for Chesapeake to Hawaii

See prices for flight routes from nearby airports that may be better suited for you.
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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 January 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$387Average$933FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$492Average$1,005FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$518Average$1,017FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$733Average$861FlexibilityNo cancel feeOn-time63%

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