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$358+ 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 7/14. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — HNL
Jun 2 — Jun 91
Tue 6/2
Tue 6/9
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 3, 2026.

This United Airlines deal was found by Cheapflights users on 4/30. 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 8/176:30 am
ORF
-
HNL
1 stop12h 58m
United Airlines
Tue 9/18:00 pm
HNL
-
ORF
1 stop13h 13m
United Airlines
Deal found 4/30$542
This Delta deal was found by Cheapflights users on 4/28. 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.
Tue 9/157:00 am
ORF
-
HNL
1 stop13h 44m
Delta
Tue 9/223:35 pm
HNL
-
ORF
1 stop13h 54m
Delta
Deal found 4/28$544
This Delta deal was found by Cheapflights users on 4/30. 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 8/119:40 am
ORF
-
HNL
2 stops17h 07m
Delta
Tue 8/253:35 pm
HNL
-
ORF
1 stop13h 54m
Delta
Deal found 4/30$548
This United Airlines deal was found by Cheapflights users on 4/29. 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 9/1510:45 am
ORF
-
HNL
2 stops15h 03m
United Airlines
Tue 9/229:40 pm
HNL
-
ORF
2 stops13h 38m
United Airlines
Deal found 4/29$603
This Delta deal was found by Cheapflights users on 5/2. 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 8/116:23 am
ORF
-
HNL
2 stops18h 48m
Delta
Wed 8/1910:46 pm
HNL
-
ORF
2 stops18h 56m
Delta
Deal found 5/2$604
This Delta deal was found by Cheapflights users on 5/1. 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 9/247:00 am
ORF
-
HNL
2 stops19h 47m
Delta
Tue 9/293:35 pm
HNL
-
ORF
1 stop13h 54m
Delta
Deal found 5/1$609
This American Airlines deal was found by Cheapflights users on 5/1. 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 9/210:40 am
ORF
-
OGG
2 stops16h 39m
American Airlines
Mon 9/71:16 pm
OGG
-
ORF
2 stops16h 49m
American Airlines
Deal found 5/1$634
This United Airlines deal was found by Cheapflights users on 5/1. 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 9/28:00 am
ORF
-
OGG
1 stop13h 05m
United Airlines
Mon 9/77:40 pm
OGG
-
ORF
1 stop13h 33m
United Airlines
Deal found 5/1$673
This United Airlines deal was found by Cheapflights users on 5/2. 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 8/146:20 am
ORF
-
OGG
2 stops14h 45m
United Airlines
Thu 8/207:40 pm
OGG
-
ORF
1 stop13h 33m
United Airlines
Deal found 5/2$679
This United Airlines deal was found by Cheapflights users on 4/30. 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 8/258:00 am
ORF
-
OGG
1 stop13h 05m
United Airlines
Wed 8/267:40 pm
OGG
-
ORF
1 stop13h 33m
United Airlines
Deal found 4/30$692
This United Airlines deal was found by Cheapflights users on 5/2. 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 8/268:00 am
ORF
-
LIH
1 stop13h 40m
United Airlines
Thu 8/277:35 pm
LIH
-
ORF
1 stop13h 38m
United Airlines
Deal found 5/2$692
This United Airlines deal was found by Cheapflights users on 4/28. 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.
Tue 9/18:00 am
ORF
-
LIH
1 stop13h 40m
United Airlines
Wed 9/21:01 pm
LIH
-
ORF
2 stops15h 09m
United Airlines
Deal found 4/28$700

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 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$542
(United Airlines)

One-way from

$358
(American Airlines)

Popular in

July

Cheapest in

February

Average price

$806
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 ($115 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 3, 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

NorfolkLihue

ORF - LIH

ORFLIH

Norfolk

Tue 6/2

6:05 am-3:37 pm

2 stops15h 32m

Lihue

Tue 6/9

2:31 pm-10:07 am

2 stops13h 36m

$753

NorfolkHonolulu

ORF - HNL

ORFHNL

Norfolk

Thu 5/28

5:20 am-7:48 pm

2 stops20h 28m

Honolulu

Thu 6/4

10:35 pm-11:15 pm

2 stops18h 40m

$765

NorfolkHonolulu

ORF - HNL

ORFHNL

Norfolk

Sun 6/28

6:20 am-7:09 pm

2 stops18h 49m

Honolulu

Mon 7/6

4:08 pm-3:50 pm

2 stops17h 42m

$785

NorfolkKailua-Kona

ORF - KOA

ORFKOA

Norfolk

Tue 6/2

10:45 am-7:47 pm

2 stops15h 02m

Kona Intl

Tue 6/9

1:52 pm-10:07 am

2 stops14h 15m

$789

NorfolkKahului

ORF - OGG

ORFOGG

Norfolk

Mon 5/18

7:08 am-7:56 pm

2 stops18h 48m

Kahului

Thu 5/21

9:20 pm-7:17 pm

2 stops15h 57m

$795

NorfolkHonolulu

ORF - HNL

ORFHNL

Norfolk

Thu 5/7

6:05 am-9:05 pm

2 stops21h 00m

Honolulu

Thu 5/14

8:55 pm-10:00 pm

2 stops19h 05m

$801

NorfolkHonolulu

ORF - HNL

ORFHNL

Norfolk

Tue 6/30

6:05 am-2:01 pm

1 stop13h 56m

Honolulu

Wed 7/8

3:50 pm-11:22 am

1 stop13h 32m

$804

NorfolkKahului

ORF - OGG

ORFOGG

Norfolk

Fri 5/15

8:00 am-3:15 pm

1 stop13h 15m

Kahului

Tue 5/19

2:05 pm-11:05 am

2 stops15h 00m

$810

NorfolkKahului

ORF - OGG

ORFOGG

Norfolk

Fri 5/15

7:08 am-7:56 pm

2 stops18h 48m

Kahului

Tue 5/19

9:48 pm-6:24 pm

2 stops14h 36m

$815

NorfolkHonolulu

ORF - HNL

ORFHNL

Norfolk

Tue 6/2

6:20 am-7:46 pm

2 stops19h 26m

Honolulu

Mon 6/8

10:40 pm-11:29 pm

2 stops18h 49m

$815

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 50 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 3, 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
4,312 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,312 reviews
Southwest
8.0
Very good
4,312 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,460 reviews
Southwest
8.0
Very good
4,312 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,682 reviews
Southwest
8.0
Very good
4,312 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,672 reviews
Southwest
8.0
Very good
4,312 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 15h 32m. United Airlines provides one of the quickest options available for as low as $753. 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.

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 May 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$320Average$907FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$492Average$949FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$518Average$1,053FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$733Average$839FlexibilityNo cancel feeOn-time63%

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