Chesapeake

$40+ Cheap flights from Chesapeake

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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — HOU
ene. 11 — ene. 181
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What to know about flights from Chesapeake

Discover essential information about flights departing from Chesapeake, including flight schedules, destinations, airlines operating at the Chesapeake airport, and any specific guidelines or requirements for travelers. Please note that the information is based on the most recent updates available. Data last updated diciembre 12, 2025.

Cheapest one-way flight

$40

Cheapest round-trip flight

$60

Cheapest airline

American Airlines

Most popular destination

Atlanta Hartsfield-Jackson (ATL)
The cheapest one-way flight from Chesapeake is currently to Orlando.
The cheapest round-trip flight from Chesapeake is currently to Orlando.
On average, American Airlines currently has the cheapest one-way flight from Chesapeake (avg. price of $242).
Atlanta Hartsfield-Jackson (ATL) is currently the most popular flight destination from Chesapeake (average round-trip price of $232).

Find flights from Chesapeake

Cheapest flights from Chesapeake
Explore the most affordable flight options available from Chesapeake. Find the lowest fares based on data from user searches, with prices last updated on diciembre 12, 2025.

This Super.com deal was found by Cheapflights users on 12/11. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 1/176:45 amORF - MCO
Nonstop2h 12mSpirit Airlines
mié. 1/214:26 pmMCO - ORF
Nonstop1h 59mSpirit Airlines
Deal found 12/11$80
This Cheapflightsfares deal was found by Cheapflights users on 12/11. 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.
sáb. 1/39:25 pmORF - FLL
Nonstop2h 24mSpirit Airlines
mié. 1/712:00 pmFLL - ORF
1 stop6h 45mSpirit Airlines
Deal found 12/11$80
This CheapOair deal was found by Cheapflights users on 12/11. 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.
dom. 1/116:45 amORF - MCO
Nonstop2h 12mSpirit Airlines
vie. 1/167:50 pmMCO - ORF
Nonstop2h 00mSpirit Airlines
Deal found 12/11$81
This Kiwi.com deal was found by Cheapflights users on 12/11. 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.
dom. 2/89:37 pmORF - MCO
Nonstop2h 15mFrontier
vie. 2/1312:26 pmMCO - ORF
Nonstop2h 07mFrontier
Deal found 12/11$82
This Spirit deal was found by Cheapflights users on 12/11. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/206:45 amORF - FLL
1 stop9h 15mSpirit Airlines
lun. 2/234:13 pmFLL - ORF
Nonstop2h 13mSpirit Airlines
Deal found 12/11$87
This Super.com deal was found by Cheapflights users on 12/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/307:40 pmORF - MCO
Nonstop2h 18mSpirit Airlines
vie. 1/97:50 pmMCO - ORF
Nonstop2h 00mSpirit Airlines
Deal found 12/10$88
This CheapOair deal was found by Cheapflights users on 12/11. 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.
lun. 2/97:33 pmORF - FLL
Nonstop2h 26mSpirit Airlines
jue. 2/1212:40 pmFLL - ORF
1 stop9h 10mSpirit Airlines
Deal found 12/11$88
This Super.com deal was found by Cheapflights users on 12/11. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 1/82:29 pmORF - MCO
Nonstop2h 15mFrontier
jue. 1/155:10 amMCO - ORF
1 stop6h 53mFrontier
Deal found 12/11$89
This Priceline deal was found by Cheapflights users on 12/10. 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.
dom. 1/43:01 pmORF - FLL
Nonstop2h 27mMultiple Airlines
sáb. 1/102:20 pmFLL - ORF
Nonstop2h 15mMultiple Airlines
Deal found 12/10$89
This Super.com deal was found by Cheapflights users on 12/11. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 1/196:45 amORF - MCO
Nonstop2h 12mSpirit Airlines
vie. 1/237:50 pmMCO - ORF
Nonstop2h 00mSpirit Airlines
Deal found 12/11$90
This CheapOair deal was found by Cheapflights users on 12/11. 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.
lun. 1/57:40 pmORF - MCO
Nonstop2h 18mSpirit Airlines
mié. 1/74:40 pmMCO - ORF
Nonstop2h 05mSpirit Airlines
Deal found 12/11$91
This CheapOair deal was found by Cheapflights users on 12/10. 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.
lun. 1/53:01 pmORF - FLL
Nonstop2h 27mSpirit Airlines
mar. 1/611:59 amFLL - ORF
Nonstop2h 07mSpirit Airlines
Deal found 12/10$91

Find flights from Chesapeake within your budget

 
Find flights departing from Chesapeake that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on diciembre 12, 2025. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

Hobby

Route

Depart

Return

Price

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

sáb. 1/17

6:45 am-8:57 am

Nonstop2h 12m

Orlando

mié. 1/21

4:26 pm-6:25 pm

Nonstop1h 59m

$80

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

sáb. 2/21

12:29 pm-2:44 pm

Nonstop2h 15m

Orlando

sáb. 2/28

1:46 pm-3:52 pm

Nonstop2h 06m

$80

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

vie. 1/30

6:45 am-8:57 am

Nonstop2h 12m

Orlando

sáb. 1/31

7:50 pm-9:50 pm

Nonstop2h 00m

$80

NorfolkFort Lauderdale

ORF - FLL

ORFFLL

Norfolk

vie. 2/20

6:45 am-4:00 pm

1 stop9h 15m

Fort Lauderdale

lun. 2/23

4:13 pm-6:26 pm

Nonstop2h 13m

$87

NorfolkFort Lauderdale

ORF - FLL

ORFFLL

Norfolk

vie. 1/16

6:45 am-4:19 pm

1 stop9h 34m

Fort Lauderdale

lun. 1/19

4:25 pm-6:38 pm

Nonstop2h 13m

$98

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

mié. 2/18

7:31 pm-11:54 pm

1 stop4h 23m

Orlando

mar. 2/24

10:00 am-12:05 pm

Nonstop2h 05m

$100

NorfolkFort Lauderdale

ORF - FLL

ORFFLL

Norfolk

jue. 2/19

7:31 pm-9:58 pm

Nonstop2h 27m

Fort Lauderdale

lun. 2/23

4:13 pm-6:26 pm

Nonstop2h 13m

$100

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

vie. 1/30

11:43 am-7:54 pm

1 stop8h 11m

Orlando

sáb. 1/31

6:10 pm-8:15 pm

Nonstop2h 05m

$104

NorfolkFort Lauderdale

ORF - FLL

ORFFLL

Norfolk

vie. 1/2

3:01 pm-5:28 pm

Nonstop2h 27m

Fort Lauderdale

mar. 1/6

12:00 pm-6:45 pm

1 stop6h 45m

$109

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

mié. 1/7

7:40 pm-9:58 pm

Nonstop2h 18m

Orlando

lun. 1/12

5:20 am-10:45 am

1 stop5h 25m

$121

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 60 results
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Best time to book a flight from Chesapeake

Have a flexible travel schedule? Discover the best time to fly 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.

Travel insights for flights from Chesapeake

Get recent, data-driven insights about flights from Chesapeake including ideal travel times, pricing trends, and more.

When is the best time to book a flight from Chesapeake?

Use this chart to determine the optimal time to book a round-trip flight from Chesapeake to Hobby. Price data was last updated on December 5, 2025.

To ensure you get the cheapest price possible for a flight from Chesapeake, you should look to book at least 45 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 Chesapeake?

Currently, July is the cheapest month in which you can book a flight from Chesapeake (average of $125). Flying from Chesapeake in December will prove the most costly (average of $247). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

When is the cheapest time to fly from Chesapeake?

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

Those who are seeking the cheapest fare on flights departing from Chesapeake would be wise to consider leaving during Sunday at noon when prices are typically at their lowest. When considering other options, price-conscious travelers should avoid Thursday at noon when fares are usually the most expensive.

Airline reviews for flights from Chesapeake

Read reviews and ratings of airlines operating flights from Chesapeake. Gain insights into the quality of service, in-flight amenities, customer experiences, and overall satisfaction to choose the best airline for your Chesapeake travel. Please note that the reviews are sourced from user searches and were last updated on diciembre 12, 2025. In the last 7 days, Cheapflights users made a total of 2,558,603 searches.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Chesapeake by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Boarding

8.1

Food

7.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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Related info for your journey

Access useful and relevant information related to your journey from Chesapeake. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated diciembre 12, 2025.
  • What is the cheapest airport to fly out of Chesapeake?

    Istanbul airport offers the cheapest routes to Toronto, from $23; whereas Cheongju airport is typically cheaper if you're flying to Jeju City, from $24. It's best to make sure you are flexible on dates to find the cheapest possible flight options for your journey.

  • What is the cheapest month to fly from Chesapeake?

    July is currently the cheapest month to fly from Chesapeake. At this moment in time December is the most expensive month. These prices are determined by multiple factors and booking in advance can help keep costs down if your schedule is not as flexible.

  • Where are the cheapest places to fly to from Chesapeake?

    Check out the cheapest flights from Chesapeake to embark to:
    Fly from Istanbul to Ankara from $23 round trip
    Fly from Cheongju to Jeju City from $24 round trip
    Fly from Venice to Tirana from $30 round trip
    Fly from Bogotá to Pereira from $31 round trip
    Fly from Orlando to New York from $34 round trip

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