Chesapeake

$42+ 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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MCO
nov. 27 — dic. 41
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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 octubre 28, 2025.

Cheapest one-way flight

$43

Cheapest round-trip flight

$83

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 Boston Logan Intl.
On average, American Airlines currently has the cheapest one-way flight from Chesapeake (avg. price of $251).
Atlanta Hartsfield-Jackson (ATL) is currently the most popular flight destination from Chesapeake (average round-trip price of $278).

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 octubre 28, 2025.

This Priceline deal was found by Cheapflights users on 10/26. 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.
vie. 11/289:26 pmORF - MCO
Nonstop2h 03mSpirit Airlines
lun. 12/16:32 pmMCO - ORF
Nonstop1h 59mSpirit Airlines
Deal found 10/26$95
This Priceline deal was found by Cheapflights users on 10/26. 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.
mié. 2/48:32 pmORF - MCO
Nonstop2h 10mMultiple Airlines
mar. 2/1010:13 amMCO - ORF
Nonstop2h 02mMultiple Airlines
Deal found 10/26$96
This Trip.com deal was found by Cheapflights users on 10/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/101:19 pmORF - MCO
Nonstop2h 11mSpirit Airlines
lun. 11/1710:27 amMCO - ORF
Nonstop1h 57mSpirit Airlines
Deal found 10/28$98
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
lun. 11/104:57 pmORF - MCO
Nonstop2h 15mMultiple Airlines
vie. 11/1410:27 amMCO - ORF
Nonstop1h 57mMultiple Airlines
Deal found 10/28$102
This Cheapflightsfares deal was found by Cheapflights users on 10/27. 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.
mié. 11/126:33 pmORF - MCO
Nonstop2h 11mSpirit Airlines
vie. 11/1410:27 amMCO - ORF
Nonstop1h 57mSpirit Airlines
Deal found 10/27$103
This Priceline deal was found by Cheapflights users on 10/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/116:33 pmORF - MCO
Nonstop2h 11mSpirit Airlines
vie. 11/1410:27 amMCO - ORF
Nonstop1h 57mSpirit Airlines
Deal found 10/28$104
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/207:18 pmORF - MCO
1 stop4h 07mSpirit Airlines
dom. 11/236:32 pmMCO - ORF
Nonstop1h 59mSpirit Airlines
Deal found 10/28$105
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
vie. 12/128:38 amORF - MCO
Nonstop2h 12mSpirit Airlines
jue. 12/184:40 pmMCO - ORF
Nonstop2h 05mSpirit Airlines
Deal found 10/27$106
This Cheapflightsfares deal was found by Cheapflights users on 10/27. 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.
mié. 11/269:26 pmORF - MCO
Nonstop2h 03mSpirit Airlines
lun. 12/16:32 pmMCO - ORF
Nonstop1h 59mSpirit Airlines
Deal found 10/27$109
This Priceline deal was found by Cheapflights users on 10/27. 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.
lun. 11/1011:42 amORF - MCO
1 stop9h 24mFrontier
jue. 11/135:25 amMCO - ORF
1 stop9h 00mFrontier
Deal found 10/27$110
This Booking.com deal was found by Cheapflights users on 10/27. 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.
sáb. 11/229:26 pmORF - MCO
Nonstop2h 03mSpirit Airlines
lun. 11/246:32 pmMCO - ORF
Nonstop1h 59mSpirit Airlines
Deal found 10/27$112
This Mytrip deal was found by Cheapflights users on 10/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/186:33 pmORF - MCO
Nonstop2h 11mSpirit Airlines
mié. 11/196:00 amMCO - ORF
2 stops12h 58mSpirit Airlines
Deal found 10/28$113

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 octubre 28, 2025. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

Orlando

Route

Depart

Return

Price

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

sáb. 4/25

7:25 am-9:35 am

Nonstop2h 10m

Orlando

mié. 4/29

10:15 am-12:15 pm

Nonstop2h 00m

$123

NorfolkAtlanta

ORF - ATL

ORFATL

Norfolk

jue. 12/11

8:38 am-3:58 pm

1 stop7h 20m

Atlanta Hartsfield-Jackson

lun. 12/15

2:41 pm-4:20 pm

Nonstop1h 39m

$141

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

mié. 12/3

6:15 pm-10:30 pm

1 stop4h 15m

Orlando

sáb. 1/17

8:45 am-10:40 am

Nonstop1h 55m

$145

NorfolkAtlanta

ORF - ATL

ORFATL

Norfolk

jue. 12/11

8:38 am-3:58 pm

1 stop7h 20m

Atlanta Hartsfield-Jackson

lun. 12/15

9:01 am-7:16 pm

1 stop10h 15m

$146

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

lun. 1/5

6:15 am-2:55 pm

2 stops8h 40m

Orlando

vie. 1/9

1:25 pm-3:25 pm

Nonstop2h 00m

$152

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

vie. 12/5

4:10 pm-6:15 pm

Nonstop2h 05m

Orlando

mar. 12/9

1:40 pm-3:30 pm

Nonstop1h 50m

$153

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

dom. 12/7

6:00 pm-8:10 pm

Nonstop2h 10m

Orlando

sáb. 12/13

8:55 am-10:50 am

Nonstop1h 55m

$153

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

lun. 12/8

10:05 am-4:15 pm

1 stop6h 10m

Orlando

mié. 12/10

1:40 pm-3:30 pm

Nonstop1h 50m

$163

NorfolkAtlanta

ORF - ATL

ORFATL

Norfolk

sáb. 11/22

4:00 pm-6:05 pm

Nonstop2h 05m

Atlanta Hartsfield-Jackson

sáb. 11/29

2:26 pm-4:08 pm

Nonstop1h 42m

$170

NorfolkAtlanta

ORF - ATL

ORFATL

Norfolk

sáb. 11/22

7:18 pm-12:15 am

1 stop4h 57m

Atlanta Hartsfield-Jackson

dom. 11/23

5:45 am-8:31 pm

1 stop14h 46m

$171

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

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 Orlando. Price data was last updated on October 24, 2025.

To ensure you get the cheapest price possible for a flight from Chesapeake, you should look to book at least 31 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, September is the cheapest month in which you can book a flight from Chesapeake (average of $40). Flying from Chesapeake in December will prove the most costly (average of $86). 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 Orlando. Price data was last updated on October 26, 2025.

Those who are seeking the cheapest fare on flights departing from Chesapeake would be wise to consider leaving during Tuesday evenings when prices are typically at their lowest. When considering other options, price-conscious travelers should avoid Wednesday 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 octubre 28, 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 American 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.

Food

7.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

8.1

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

Food

7.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

8.1

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

Food

7.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

8.1

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

Food

7.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

8.1

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

Food

7.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

8.1

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

Food

7.0

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

8.1

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

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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 octubre 28, 2025.
  • What is the cheapest airport to fly out of Chesapeake?

    Istanbul airport offers the cheapest routes to Shanghai, 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?

    September 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 Medellín to Montería from $27 round trip
    Fly from Larnaca to Tel Aviv from $27 round trip
    Fly from Stockholm to Luleå from $28 round trip

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