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Chesapeake

$71+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — RIC
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheapflights Tip: The best prices from Houston to Chesapeake are usually found in August or February, booked 57 days in advance, depart on a Thursday or Saturday and return on a Tuesday

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 September 17, 2025.

Round-trip from

$143
(Cheapflightsfares)

One-way from

$71
(Priceline)

Popular in

November

Cheapest in

August

Average price

$408
From Houston to Chesapeake
Search Deals
One-way flight from Houston to Chesapeake
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Highest demand for flights based on searches. 8% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 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 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 September 17, 2025.

This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/116:05 amIAH - ORF
1 stop5h 22mFrontier
Sat 10/181:22 pmORF - IAH
1 stop6h 07mFrontier
Deal found 9/16$143
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/218:05 amIAH - ORF
1 stop7h 44mFrontier
Thu 10/234:14 pmORF - IAH
1 stop6h 35mFrontier
Deal found 9/15$144
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/166:05 amIAH - ORF
1 stop7h 49mFrontier
Sun 10/199:47 amORF - IAH
1 stop22h 17mFrontier
Deal found 9/16$152
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/14:36 pmIAH - ORF
1 stop22h 36mFrontier
Mon 10/612:19 pmORF - IAH
1 stop10h 34mFrontier
Deal found 9/16$156
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/186:05 amIAH - ORF
1 stop5h 22mFrontier
Sun 10/199:47 amORF - IAH
1 stop22h 17mFrontier
Deal found 9/15$157
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/228:37 pmIAH - ORF
1 stop11h 25mFrontier
Sun 10/269:47 amORF - IAH
1 stop22h 17mFrontier
Deal found 9/15$158
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/236:05 amIAH - ORF
1 stop7h 49mFrontier
Sun 10/269:47 amORF - IAH
1 stop22h 17mFrontier
Deal found 9/16$169
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/147:35 amIAH - ORF
1 stop6h 41mAmerican Airlines
Tue 10/214:06 pmORF - IAH
2 stops7h 01mAmerican Airlines
Deal found 9/16$174
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/65:10 amHOU - ORF
1 stop9h 25mSouthwest
Sat 11/85:30 pmORF - HOU
1 stop5h 45mSouthwest
Deal found 9/15$183
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3012:55 pmIAH - ORF
1 stop8h 51mMultiple Airlines
Sun 11/21:06 pmORF - IAH
1 stop21h 27mMultiple Airlines
Deal found 9/16$188
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/236:05 amIAH - ORF
1 stop7h 49mMultiple Airlines
Mon 10/276:16 pmORF - IAH
1 stop6h 49mMultiple Airlines
Deal found 9/16$190
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/65:40 amHOU - ORF
1 stop4h 45mSouthwest
Tue 10/75:05 pmORF - HOU
1 stop6h 55mSouthwest
Deal found 9/15$218

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 September 17, 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

Thu 10/23

6:05 am-2:54 pm

1 stop7h 49m

Norfolk

Sun 10/26

9:47 am-7:04 am

1 stop22h 17m

$170

HoustonNorfolk

HOU - ORF

HOUORF

Houston Hobby

Thu 11/6

5:10 am-3:35 pm

1 stop9h 25m

Norfolk

Sat 11/8

5:30 pm-10:15 pm

1 stop5h 45m

$183

HoustonNorfolk

IAH - ORF

IAHORF

Houston George Bush Intcntl

Thu 10/30

12:55 pm-10:46 pm

1 stop8h 51m

Norfolk

Sun 11/2

1:06 pm-9:33 am

1 stop21h 27m

$188

HoustonNorfolk

IAH - ORF

IAHORF

Houston George Bush Intcntl

Mon 11/10

4:42 pm-11:40 pm

1 stop5h 58m

Norfolk

Tue 11/18

8:01 am-12:32 pm

1 stop5h 31m

$203

HoustonNorfolk

HOU - ORF

HOUORF

Houston Hobby

Mon 10/6

5:40 am-11:25 am

1 stop4h 45m

Norfolk

Tue 10/7

5:05 pm-11:00 pm

1 stop6h 55m

$218

HoustonNorfolk

IAH - ORF

IAHORF

Houston George Bush Intcntl

Sat 10/18

7:00 am-10:03 pm

2 stops14h 03m

Norfolk

Sat 10/25

1:22 pm-6:29 pm

1 stop6h 07m

$227

HoustonNorfolk

IAH - ORF

IAHORF

Houston George Bush Intcntl

Thu 11/6

4:42 pm-10:48 am

2 stops17h 06m

Norfolk

Sat 11/8

8:01 am-5:42 pm

1 stop10h 41m

$230

HoustonNorfolk

IAH - ORF

IAHORF

Houston George Bush Intcntl

Thu 10/23

9:54 pm-4:39 pm

2 stops17h 45m

Norfolk

Sun 10/26

9:47 am-7:04 am

1 stop22h 17m

$230

HoustonNorfolk

HOU - ORF

HOUORF

Houston Hobby

Sat 11/22

10:10 pm-10:55 am

1 stop11h 45m

Norfolk

Tue 11/25

5:55 pm-12:05 am

1 stop7h 10m

$243

HoustonNorfolk

HOU - ORF

HOUORF

Houston Hobby

Wed 11/19

3:45 pm-10:00 pm

1 stop5h 15m

Norfolk

Wed 12/3

12:15 pm-6:15 pm

1 stop7h 00m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 38 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 September 12, 2025.

To ensure you get the cheapest price possible for a flight from Houston to Chesapeake, you should look to book at least 57 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, January is the cheapest month in which you can book a flight from Houston to Chesapeake (average of $281). Flying from Houston to Chesapeake in March is currently the most expensive (average of $351). 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 September 17, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Houston to Chesapeake as you normally would.

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 Wednesday at noon when fares are most often at their lowest. Tuesday afternoons 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 September 17, 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
4,242 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

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

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

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
7,961 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

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
8,926 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

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

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

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
8,023 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Crew

8.6

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 $203, Frontier can have you in Chesapeake from Houston in 5h 58m. 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 $72. American Airlines flights start at $115 while deals on Delta start at $119 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, January is the cheapest month in which you can book a flight from Houston to Chesapeake (average of $281). Flying from Houston to Chesapeake in March is currently the most expensive (average of $351). 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 5 airlines flying from Houston to Chesapeake

Discover the top 5 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$117Average$228FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$188Average$393FlexibilityNo cancel feeOn-time71%
DeltaCheapest$236Average$339FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$242Average$392FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$244Average$461FlexibilityNo cancel feeOn-time69%

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