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Chesapeake

$54+ 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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — RIC
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
1 adult, Economy
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Cheapflights Tip: The best prices from Houston to Chesapeake are usually found in August or September, booked 75 days in advance, depart on a Thursday or Saturday and return on a Tuesday

Find 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 November 2, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/1. 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 11/206:04 amIAH - ORF
1 stop5h 10mFrontier
Sun 11/232:10 pmORF - IAH
1 stop20h 29mFrontier
Deal found 11/1$148
This Priceline deal was found by Cheapflights users on 11/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/86:05 amIAH - ORF
1 stop9h 15mMultiple Airlines
Thu 12/118:38 amORF - IAH
1 stop9h 31mMultiple Airlines
Deal found 11/2$153
This Mytrip deal was found by Cheapflights users on 11/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/910:41 amIAH - ORF
1 stop7h 35mSpirit Airlines
Sat 12/138:11 pmORF - IAH
2 stops16h 34mSpirit Airlines
Deal found 11/2$165
This Priceline deal was found by Cheapflights users on 11/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/156:05 amIAH - ORF
1 stop9h 15mMultiple Airlines
Wed 12/313:01 pmORF - IAH
1 stop7h 53mMultiple Airlines
Deal found 11/1$175
This Trip.com deal was found by Cheapflights users on 10/31. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/288:29 amIAH - ORF
1 stop11h 02mMultiple Airlines
Fri 12/512:00 pmORF - IAH
1 stop6h 30mMultiple Airlines
Deal found 10/31$177
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/812:50 pmIAH - ORF
1 stop25h 51mMultiple Airlines
Sat 12/137:00 amORF - IAH
1 stop29h 45mMultiple Airlines
Deal found 11/2$179
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/910:41 amIAH - ORF
1 stop7h 35mMultiple Airlines
Sat 12/137:00 amORF - IAH
1 stop29h 45mMultiple Airlines
Deal found 11/2$182
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Sat 11/228:08 pmIAH - ORF
1 stop16h 07mMultiple Airlines
Sun 11/309:26 pmORF - IAH
1 stop23h 23mMultiple Airlines
Deal found 11/1$199
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Fri 11/215:34 amIAH - ORF
1 stop12h 33mMultiple Airlines
Sun 11/232:10 pmORF - IAH
1 stop20h 29mMultiple Airlines
Deal found 11/1$201
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/266:09 pmIAH - ORF
1 stop23h 14mMultiple Airlines
Wed 12/37:00 amORF - IAH
1 stop26h 34mMultiple Airlines
Deal found 11/2$203
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/228:08 pmIAH - ORF
1 stop16h 07mMultiple Airlines
Tue 11/259:26 pmORF - IAH
1 stop20h 29mMultiple Airlines
Deal found 11/2$204
This Delta deal was found by Cheapflights users on 10/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/236:00 amHOU - ORF
1 stop4h 31mDelta
Thu 11/274:00 pmORF - HOU
1 stop8h 07mDelta
Deal found 10/31$269

Cheap flight deals from Houston to Chesapeake

Keep the following information in mind while searching for Houston to Chesapeake flight deals. Data was last updated November 2, 2025.

Round-trip from

$148
(Kiwi.com)

One-way from

$54
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$436
From Houston to Chesapeake
Search Deals
One-way flight from Houston to Chesapeake
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($25 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 2, 2025.
Use the filters below to find and compare flights from Houston to Chesapeake that are best for you.

Fly from

Houston

Fly to

Chesapeake

Route

Depart

Return

Price

HoustonNorfolk

IAH - ORF

IAHORF

Houston George Bush Intcntl

Wed 11/26

6:09 pm-6:23 pm

1 stop23h 14m

Norfolk

Wed 12/3

8:02 pm-8:34 am

2 stops13h 32m

$219

HoustonNorfolk

IAH - ORF

IAHORF

Houston George Bush Intcntl

Thu 12/18

6:30 pm-10:26 pm

Nonstop2h 56m

Norfolk

Sat 12/20

5:15 pm-11:12 pm

1 stop6h 57m

$259

HoustonNorfolk

IAH - ORF

IAHORF

Houston George Bush Intcntl

Tue 12/9

6:30 pm-10:30 pm

Nonstop3h 00m

Norfolk

Sat 12/13

4:45 pm-11:59 pm

1 stop8h 14m

$259

HoustonNorfolk

HOU - ORF

HOUORF

Houston Hobby

Wed 11/26

6:00 am-2:06 pm

1 stop7h 06m

Norfolk

Wed 12/3

6:30 am-1:28 pm

1 stop7h 58m

$269

HoustonNorfolk

HOU - ORF

HOUORF

Houston Hobby

Mon 12/8

8:55 am-4:45 pm

1 stop6h 50m

Norfolk

Thu 12/11

5:30 pm-11:20 pm

1 stop6h 50m

$269

HoustonNorfolk

HOU - ORF

HOUORF

Houston Hobby

Wed 11/26

6:00 am-2:06 pm

1 stop7h 06m

Norfolk

Thu 12/4

8:30 am-1:28 pm

1 stop5h 58m

$269

HoustonNorfolk

HOU - ORF

HOUORF

Houston Hobby

Tue 11/25

6:48 pm-12:13 am

1 stop4h 25m

Norfolk

Tue 12/2

6:02 pm-10:48 pm

1 stop5h 46m

$269

HoustonNorfolk

HOU - ORF

HOUORF

Houston Hobby

Mon 12/8

6:47 pm-12:32 am

1 stop4h 45m

Norfolk

Sat 12/13

5:25 pm-10:33 pm

1 stop6h 08m

$269

HoustonNorfolk

HOU - ORF

HOUORF

Houston Hobby

Sun 11/23

6:48 pm-12:13 am

1 stop4h 25m

Norfolk

Thu 11/27

4:00 pm-11:07 pm

1 stop8h 07m

$269

HoustonNorfolk

IAH - ORF

IAHORF

Houston George Bush Intcntl

Sun 11/23

6:40 pm-12:13 am

1 stop4h 33m

Norfolk

Thu 11/27

4:00 pm-10:30 pm

1 stop7h 30m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 37 results
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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 October 31, 2025.

To ensure you get the cheapest price possible for a flight from Houston to Chesapeake, you should look to book at least 75 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 $144). 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 November 2, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 29% on flights from Houston to Chesapeake by exploring options for tickets at noon.

What is the cheapest day to fly from Houston to Chesapeake?

Use this chart to determine the cheapest time to fly round-trip from Houston to Chesapeake. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Houston to Chesapeake flight should consider departing on Friday evenings when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 November 2, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United 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.
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Overall

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
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Overall

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
7.9
Good
8,001 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Overall

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
8,997 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Overall

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
11,034 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Overall

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
Spirit Airlines
6.3
Okay
8,120 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Food

7.0

Overall

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 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 $259, Spirit Airlines can have you in Chesapeake from Houston in 2h 56m. Airlines will cover a distance of 1199 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 $54. Spirit Airlines flights start at $57 while deals on Southwest start at $135 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 $144). 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

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Alternative routes for Houston to Chesapeake

See prices for flight routes from nearby airports that may be better suited for you.
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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 November 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$117Average$229FlexibilityNo cancel feeOn-time65%
FrontierCheapest$144Average$144FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$228Average$417FlexibilityNo cancel feeOn-time71%
DeltaCheapest$236Average$339FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$239Average$445FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$242Average$385FlexibilityNo cancel feeOn-time63%

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