Chesapeake

$65+ Cheap flights from Houston to Chesapeake, VA

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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — RIC
May 1 — May 81
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Houston to Chesapeake with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Houston to Chesapeake

Cheapest flights from Houston to Chesapeake
Explore the most affordable flight options available from Houston to Chesapeake. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 1, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/138:50 pm
IAH
-
ORF
1 stop13h 21m
Frontier
Wed 5/2012:06 pm
ORF
-
IAH
1 stop11h 44m
Frontier
Deal found 3/28$131
This Kiwi.com deal was found by Cheapflights users on 3/31. 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.
Wed 4/296:14 pm
IAH
-
ORF
1 stop15h 18m
Frontier
Tue 5/512:06 pm
ORF
-
IAH
1 stop11h 44m
Frontier
Deal found 3/31$134
This Priceline deal was found by Cheapflights users on 3/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/257:00 am
IAH
-
ORF
1 stop6h 20m
Multiple Airlines
Sun 4/2611:27 am
ORF
-
IAH
1 stop6h 51m
Multiple Airlines
Deal found 3/30$143
This Kiwi.com deal was found by Cheapflights users on 3/31. 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.
Fri 5/112:35 pm
IAH
-
ORF
1 stop20h 57m
Multiple Airlines
Mon 5/412:31 pm
ORF
-
IAH
1 stop27h 27m
Multiple Airlines
Deal found 3/31$146
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:04 pm
IAH
-
ORF
1 stop22h 17m
Frontier
Wed 5/612:06 pm
ORF
-
IAH
1 stop11h 44m
Frontier
Deal found 3/30$149
This Kiwi.com deal was found by Cheapflights users on 3/31. 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.
Wed 4/296:14 pm
IAH
-
ORF
1 stop15h 18m
Multiple Airlines
Sat 5/211:27 am
ORF
-
IAH
1 stop13h 02m
Multiple Airlines
Deal found 3/31$152
This Kiwi.com deal was found by Cheapflights users on 3/31. 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.
Tue 5/267:44 pm
IAH
-
ORF
2 stops38h 27m
Frontier
Tue 6/912:21 pm
ORF
-
IAH
1 stop11h 27m
Frontier
Deal found 3/31$153
This CheapOair deal was found by Cheapflights users on 3/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/187:00 am
IAH
-
ORF
1 stop6h 20m
Multiple Airlines
Sun 4/2611:27 am
ORF
-
IAH
1 stop6h 51m
Multiple Airlines
Deal found 3/28$154
This Kiwi.com deal was found by Cheapflights users on 3/31. 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.
Fri 5/16:14 pm
IAH
-
ORF
1 stop15h 18m
Frontier
Mon 5/412:31 pm
ORF
-
IAH
1 stop11h 19m
Frontier
Deal found 3/31$157
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/148:02 pm
IAH
-
ORF
1 stop14h 09m
Frontier
Mon 5/1812:06 pm
ORF
-
IAH
1 stop27h 52m
Frontier
Deal found 4/1$159
This Southwest deal was found by Cheapflights users on 3/31. 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 5/128:55 am
HOU
-
ORF
1 stop5h 55m
Southwest
Sat 5/167:55 am
ORF
-
HOU
1 stop5h 45m
Southwest
Deal found 3/31$309
This Southwest deal was found by Cheapflights users on 3/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:40 pm
HOU
-
ORF
1 stop11h 35m
Southwest
Tue 6/93:40 pm
ORF
-
HOU
1 stop5h 50m
Southwest
Deal found 3/30$314

Find flight deals from Houston to Chesapeake

Keep the following information in mind while searching for Houston to Chesapeake flight deals. Data was last updated April 1, 2026.

Round-trip from

$131
(Kiwi.com)

One-way from

$65
(Cheapflightsfares)

Popular in

November

Cheapest in

August

Average price

$416
From Houston to Chesapeake
One-way flight from Houston to Chesapeake
Highest demand for flights based on searches. 4% potential increase in price ($17 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Average for round-trip flights in April 2026

Cheapflights Fare Finder

 
Customize your flight search to find flights from Houston to Chesapeake 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 April 1, 2026.
Use the filters below to find and compare flights from Houston to Chesapeake that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HoustonNorfolk

HOU - ORF

HOUORF

Houston Hobby

Tue 5/12

7:15 am-3:50 pm

1 stop7h 35m

Norfolk

Sat 5/16

10:20 am-5:00 pm

2 stops7h 40m

$314

HoustonNorfolk

IAH - ORF

IAHORF

Houston George Bush Intcntl

Wed 7/8

1:46 pm-9:42 pm

1 stop6h 56m

Norfolk

Tue 7/14

6:15 am-8:20 am

Nonstop3h 05m

$319

HoustonNorfolk

HOU - ORF

HOUORF

Houston Hobby

Sat 5/2

10:48 am-4:24 pm

1 stop4h 36m

Norfolk

Sun 5/3

5:50 am-9:58 am

1 stop5h 08m

$329

HoustonNorfolk

HOU - ORF

HOUORF

Houston Hobby

Wed 4/29

10:53 am-4:24 pm

1 stop4h 31m

Norfolk

Mon 5/4

5:50 am-9:58 am

1 stop5h 08m

$329

HoustonNorfolk

HOU - ORF

HOUORF

Houston Hobby

Fri 4/24

5:05 pm-10:55 pm

1 stop4h 50m

Norfolk

Sun 4/26

10:20 am-4:00 pm

1 stop6h 40m

$329

HoustonNorfolk

HOU - ORF

HOUORF

Houston Hobby

Fri 5/1

10:53 am-4:24 pm

1 stop4h 31m

Norfolk

Sun 5/3

5:50 am-9:58 am

1 stop5h 08m

$329

HoustonNorfolk

HOU - ORF

HOUORF

Houston Hobby

Thu 5/14

1:06 pm-9:18 pm

1 stop7h 12m

Norfolk

Sun 5/17

5:20 am-9:32 am

1 stop5h 12m

$329

HoustonNorfolk

IAH - ORF

IAHORF

Houston George Bush Intcntl

Tue 4/28

6:46 pm-12:37 am

1 stop4h 51m

Norfolk

Tue 5/5

7:00 am-11:14 am

1 stop5h 14m

$329

HoustonNorfolk

IAH - ORF

IAHORF

Houston George Bush Intcntl

Fri 7/17

6:37 pm-12:45 am

1 stop5h 08m

Norfolk

Sun 7/19

4:55 pm-9:24 pm

1 stop5h 29m

$329

HoustonNorfolk

IAH - ORF

IAHORF

Houston George Bush Intcntl

Fri 4/24

6:15 am-2:20 pm

1 stop7h 05m

Norfolk

Sun 4/26

6:08 am-8:46 am

Nonstop3h 38m

$348

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

Showing 1-10 of 40 resultsSorted by cheapest first
1
2
3
4

Best time to book a flight from Houston to Chesapeake

Have a flexible travel schedule? Discover the best time to fly to Chesapeake from Houston 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 Houston to Chesapeake

How far ahead should I book a flight from Houston to Chesapeake?

Use this chart to determine the optimal time to book a round-trip flight from Houston to Chesapeake. Price data was last updated on March 13, 2026.

To ensure you get the cheapest price possible for a flight from Houston to Chesapeake, you should look to book at least 14 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, October is the cheapest month in which you can book a flight from Houston to Chesapeake (average of $125). Flying from Houston to Chesapeake in June is currently the most expensive (average of $246). 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 HOU to C6E?

Find hourly flight availability from Houston to Chesapeake. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 1, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 17% on flights from Houston to Chesapeake by exploring options for tickets in the morning.

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

Reviews of airlines servicing Chesapeake

Get insights into the airlines that provide service to Chesapeake. 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 Chesapeake. Reviews last updated April 1, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited Airlines from Houston to Chesapeake. 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.

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

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.

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

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.

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

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.

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

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.

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

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.

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

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 Houston to Chesapeake. 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 Houston to Chesapeake?

    For as low as $329, Southwest can have you in Chesapeake from Houston in 4h 36m. Airlines will cover a distance of 1207 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 Houston to Chesapeake one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $55. American Airlines flights start at $68 while deals on Spirit Airlines start at $80 one-way.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Houston to Chesapeake 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 Houston to Chesapeake?

    Currently, October is the cheapest month in which you can book a flight from Houston to Chesapeake (average of $125). Flying from Houston to Chesapeake in June is currently the most expensive (average of $246). 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 Houston to Chesapeake

See prices for flight routes from nearby airports that may be better suited for you.

Top 6 airlines flying from Houston to Chesapeake

Discover the top 6 airlines that operate flights from Houston to Chesapeake. 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 April 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$107Average$191FlexibilityNo cancel feeOn-time65%
FrontierCheapest$144Average$162FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$194Average$375FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$204Average$387FlexibilityNo cancel feeOn-time71%
DeltaCheapest$222Average$334FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$229Average$430FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.