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$265+ 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 11/28. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — HNL
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
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 September 16, 2025.

Round-trip from

$529
(Delta)

One-way from

$265
(Delta)

Popular in

December

Cheapest in

February

Average price

$838
From Chesapeake to Hawaii
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One-way flight from Chesapeake to Hawaii
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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 2% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 16, 2025.

This American Airlines deal was found by Cheapflights users on 9/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/117:32 amORF - HNL
1 stop12h 51mAmerican Airlines
Tue 11/187:00 pmHNL - ORF
1 stop11h 47mAmerican Airlines
Deal found 9/14$529
This United Airlines deal was found by Cheapflights users on 9/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/118:03 amORF - HNL
1 stop13h 30mUnited Airlines
Wed 11/192:25 pmHNL - ORF
2 stops14h 21mUnited Airlines
Deal found 9/16$535
This American Airlines deal was found by Cheapflights users on 9/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/226:14 amORF - HNL
2 stops16h 43mAmerican Airlines
Mon 10/275:45 pmHNL - ORF
2 stops15h 01mAmerican Airlines
Deal found 9/14$540
This American Airlines deal was found by Cheapflights users on 9/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/75:51 amORF - OGG
2 stops14h 33mAmerican Airlines
Fri 12/122:47 pmOGG - ORF
2 stops14h 07mAmerican Airlines
Deal found 9/13$540
This United Airlines deal was found by Cheapflights users on 9/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/78:04 amORF - OGG
1 stop13h 32mUnited Airlines
Fri 12/1211:45 pmOGG - ORF
2 stops17h 05mUnited Airlines
Deal found 9/13$556
This Delta deal was found by Cheapflights users on 9/16. 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 12/35:15 amORF - KOA
2 stops19h 11mDelta
Wed 12/108:53 pmKOA - ORF
2 stops15h 14mDelta
Deal found 9/16$565
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/225:24 amORF - HNL
1 stop14h 08mDelta
Mon 10/274:45 pmHNL - ORF
1 stop13h 30mDelta
Deal found 9/15$576
This American Airlines deal was found by Cheapflights users on 9/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/267:43 amORF - HNL
1 stop12h 31mAmerican Airlines
Wed 12/37:00 pmHNL - ORF
1 stop11h 25mAmerican Airlines
Deal found 9/14$626
This American Airlines deal was found by Cheapflights users on 9/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/56:21 amORF - OGG
1 stop13h 57mAmerican Airlines
Tue 11/112:46 pmOGG - ORF
2 stops16h 01mAmerican Airlines
Deal found 9/13$631
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/27:10 amORF - HNL
1 stop13h 33mDelta
Mon 10/63:02 pmHNL - ORF
1 stop11h 58mDelta
Deal found 9/15$656
This American Airlines deal was found by Cheapflights users on 9/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/126:21 amORF - OGG
1 stop14h 01mAmerican Airlines
Wed 12/248:00 pmOGG - ORF
1 stop13h 28mAmerican Airlines
Deal found 9/14$656
This United Airlines deal was found by Cheapflights users on 9/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/126:05 amORF - OGG
2 stops15h 51mUnited Airlines
Wed 12/245:15 pmOGG - ORF
1 stop12h 23mUnited Airlines
Deal found 9/14$662

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 September 16, 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

NorfolkHonolulu

ORF - HNL

ORFHNL

Norfolk

Mon 11/10

5:40 am-3:09 pm

1 stop14h 29m

Honolulu

Fri 11/14

5:15 pm-11:29 am

1 stop13h 14m

$529

NorfolkHonolulu

ORF - HNL

ORFHNL

Norfolk

Thu 1/29

8:00 am-4:43 pm

1 stop13h 43m

Honolulu

Tue 2/10

5:00 pm-9:52 am

1 stop11h 52m

$529

NorfolkKahului

ORF - OGG

ORFOGG

Norfolk

Sun 1/11

6:29 am-3:20 pm

1 stop13h 51m

Kahului

Sun 1/18

2:43 pm-9:37 am

2 stops13h 54m

$535

NorfolkHonolulu

ORF - HNL

ORFHNL

Norfolk

Tue 10/14

6:15 am-1:27 pm

1 stop13h 12m

Honolulu

Tue 10/21

8:10 pm-6:30 pm

2 stops16h 20m

$535

NorfolkKailua-Kona

ORF - KOA

ORFKOA

Norfolk

Mon 2/2

5:50 am-7:27 pm

2 stops18h 37m

Kona Intl

Mon 2/9

6:30 pm-2:02 pm

1 stop14h 32m

$535

NorfolkHonolulu

ORF - HNL

ORFHNL

Norfolk

Wed 11/12

8:03 am-4:33 pm

1 stop13h 30m

Honolulu

Wed 11/19

2:25 pm-10:49 am

2 stops15h 24m

$535

NorfolkHonolulu

ORF - HNL

ORFHNL

Norfolk

Tue 1/27

7:39 am-8:06 pm

2 stops17h 27m

Honolulu

Sat 2/7

2:35 pm-9:37 am

2 stops14h 02m

$540

NorfolkHonolulu

ORF - HNL

ORFHNL

Norfolk

Fri 12/5

6:00 am-3:23 pm

2 stops14h 23m

Honolulu

Sun 12/7

2:38 pm-9:46 am

2 stops14h 08m

$540

NorfolkLihue

ORF - LIH

ORFLIH

Norfolk

Mon 2/2

6:29 am-7:46 pm

2 stops18h 17m

Lihue

Mon 2/9

10:10 pm-7:47 pm

2 stops16h 37m

$540

NorfolkKahului

ORF - OGG

ORFOGG

Norfolk

Sun 12/7

8:04 am-4:36 pm

1 stop13h 32m

Kahului

Fri 12/12

11:45 pm-9:50 pm

2 stops17h 05m

$556

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 42 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 $469). Flying from Chesapeake to Hawaii in June is currently the most expensive (average of $687). 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.

What is the cheapest time of day to fly from C6E to HI?

Find hourly flight availability from Chesapeake to Hawaii. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

When flying from Chesapeake to Hawaii, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 September 16, 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
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,957 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,924 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 13h 43m. Delta provides one of the quickest options available for as low as $529. 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 $265. 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 $469). Flying from Chesapeake to Hawaii in June is currently the most expensive (average of $687). 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.

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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$449Average$951FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$471Average$861FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$492Average$1,007FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$518Average$995FlexibilityNo cancel feeOn-time71%

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