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Chesapeake

$25+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — HOU
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
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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 January 27, 2026.

Cheapest one-way flight

$25

Cheapest round-trip flight

$28

Cheapest airline

American Airlines

Most popular destination

Atlanta Hartsfield-Jackson (ATL)
The cheapest one-way flight from Chesapeake is currently to Fort Lauderdale.
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The cheapest round-trip flight from Chesapeake is currently to Fort Lauderdale.
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On average, American Airlines currently has the cheapest one-way flight from Chesapeake (avg. price of $248).
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Atlanta Hartsfield-Jackson (ATL) is currently the most popular flight destination from Chesapeake (average round-trip price of $262).
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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 January 27, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 1/25. 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.
Sun 2/87:33 pm
ORF
-
FLL
Nonstop2h 26m
Spirit Airlines
Sat 2/145:35 pm
FLL
-
ORF
Nonstop2h 14m
Spirit Airlines
Deal found 1/25$56
This Expedia deal was found by Cheapflights users on 1/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:44 pm
ORF
-
FLL
Nonstop2h 25m
Spirit Airlines
Wed 2/254:13 pm
FLL
-
ORF
Nonstop2h 13m
Spirit Airlines
Deal found 1/25$57
This Super.com deal was found by Cheapflights users on 1/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/78:44 pm
ORF
-
FLL
Nonstop2h 25m
Spirit Airlines
Tue 3/315:35 pm
FLL
-
ORF
Nonstop2h 11m
Spirit Airlines
Deal found 1/26$59
This Priceline deal was found by Cheapflights users on 1/26. 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.
Mon 2/97:33 pm
ORF
-
FLL
Nonstop2h 26m
Spirit Airlines
Thu 2/124:13 pm
FLL
-
ORF
Nonstop2h 13m
Spirit Airlines
Deal found 1/26$63
This Expedia deal was found by Cheapflights users on 1/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/197:31 pm
ORF
-
FLL
Nonstop2h 27m
Spirit Airlines
Tue 2/244:13 pm
FLL
-
ORF
Nonstop2h 13m
Spirit Airlines
Deal found 1/25$64
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 2/107:33 pm
ORF
-
FLL
Nonstop2h 26m
Spirit Airlines
Sat 2/145:35 pm
FLL
-
ORF
Nonstop2h 14m
Spirit Airlines
Deal found 1/25$65
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 2/97:33 pm
ORF
-
FLL
Nonstop2h 26m
Spirit Airlines
Sat 2/145:35 pm
FLL
-
ORF
Nonstop2h 14m
Spirit Airlines
Deal found 1/25$67
This Super.com deal was found by Cheapflights users on 1/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/157:31 pm
ORF
-
FLL
Nonstop2h 27m
Spirit Airlines
Tue 2/174:13 pm
FLL
-
ORF
Nonstop2h 13m
Spirit Airlines
Deal found 1/26$69
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 2/107:33 pm
ORF
-
FLL
Nonstop2h 26m
Spirit Airlines
Wed 2/184:13 pm
FLL
-
ORF
Nonstop2h 13m
Spirit Airlines
Deal found 1/25$70
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 2/107:33 pm
ORF
-
FLL
Nonstop2h 26m
Spirit Airlines
Fri 2/134:13 pm
FLL
-
ORF
Nonstop2h 13m
Spirit Airlines
Deal found 1/25$72
This Travelocity deal was found by Cheapflights users on 1/25. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/247:31 pm
ORF
-
FLL
Nonstop2h 27m
Spirit Airlines
Wed 3/412:40 pm
FLL
-
ORF
1 stop9h 10m
Spirit Airlines
Deal found 1/25$73
This Cheapflightsfares deal was found by Cheapflights users on 1/25. 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.
Fri 2/277:31 pm
ORF
-
FLL
Nonstop2h 27m
Spirit Airlines
Fri 3/64:13 pm
FLL
-
ORF
Nonstop2h 13m
Spirit Airlines
Deal found 1/25$74

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 January 27, 2026. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

Hobby

Route

Depart

Return

Price

NorfolkFort Lauderdale

ORF - FLL

ORFFLL

Norfolk

Wed 3/4

7:31 pm-9:58 pm

Nonstop2h 27m

Fort Lauderdale

Tue 3/10

4:13 pm-6:26 pm

Nonstop2h 13m

$57

NorfolkFort Lauderdale

ORF - FLL

ORFFLL

Norfolk

Wed 3/25

8:41 pm-10:59 pm

Nonstop2h 18m

Fort Lauderdale

Wed 4/1

5:35 pm-7:46 pm

Nonstop2h 11m

$59

NorfolkFort Lauderdale

ORF - FLL

ORFFLL

Norfolk

Wed 2/25

7:31 pm-9:58 pm

Nonstop2h 27m

Fort Lauderdale

Wed 3/4

12:40 pm-9:50 pm

1 stop9h 10m

$73

NorfolkFort Lauderdale

ORF - FLL

ORFFLL

Norfolk

Sun 2/8

7:33 pm-9:59 pm

Nonstop2h 26m

Fort Lauderdale

Wed 2/11

6:39 am-5:20 pm

1 stop10h 41m

$81

NorfolkFort Lauderdale

ORF - FLL

ORFFLL

Norfolk

Sun 2/8

11:45 am-7:18 am

1 stop19h 33m

Fort Lauderdale

Sat 2/14

5:35 pm-7:49 pm

Nonstop2h 14m

$90

NorfolkFort Lauderdale

ORF - FLL

ORFFLL

Norfolk

Fri 4/17

8:24 pm-10:51 pm

Nonstop2h 27m

Fort Lauderdale

Sun 4/19

5:16 pm-7:29 pm

Nonstop2h 13m

$92

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Mon 2/16

7:31 pm-11:54 pm

1 stop4h 23m

Orlando

Fri 2/20

12:26 pm-2:33 pm

Nonstop2h 07m

$97

NorfolkFort Lauderdale

ORF - FLL

ORFFLL

Norfolk

Sat 4/4

8:41 pm-10:59 pm

Nonstop2h 18m

Fort Lauderdale

Wed 4/8

5:35 pm-7:46 pm

Nonstop2h 11m

$105

NorfolkFort Lauderdale

ORF - FLL

ORFFLL

Norfolk

Fri 2/6

7:33 pm-9:59 pm

Nonstop2h 26m

Fort Lauderdale

Thu 2/12

4:13 pm-6:26 pm

Nonstop2h 13m

$107

NorfolkFort Lauderdale

ORF - FLL

ORFFLL

Norfolk

Mon 5/11

8:24 pm-10:51 pm

Nonstop2h 27m

Fort Lauderdale

Thu 5/14

5:16 pm-7:29 pm

Nonstop2h 13m

$110

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

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 Hobby. Price data was last updated on January 23, 2026.

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 $248). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

Which airlines fly from Chesapeake?

For flights departing from Chesapeake check dates and pricing for the following: United Airlines, Delta, American Airlines, Southwest, Spirit Airlines. These airlines depart to the following popular destinations: Houston.

American Airlines
American Airlines
From $164
Delta
Delta
From $88
United Airlines
United Airlines
From $138
Southwest
Southwest
From $147

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 January 27, 2026. 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.
Southwest
8.0
Very good
4,268 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

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
Southwest
8.0
Very good
4,268 reviews
Southwest
8.0
Very good
4,268 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

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
Delta
7.9
Good
8,118 reviews
Southwest
8.0
Very good
4,268 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

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
United Airlines
7.4
Good
9,205 reviews
Southwest
8.0
Very good
4,268 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

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
American Airlines
7.2
Good
11,197 reviews
Southwest
8.0
Very good
4,268 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

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
Spirit Airlines
6.3
Okay
8,384 reviews
Southwest
8.0
Very good
4,268 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

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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Popular routes from Chesapeake

These are the most popular flight routes from Chesapeake
Chesapeake to Las Vegas flights
Chesapeake to Miami flights
Chesapeake to Tampa flights
Chesapeake to Atlanta flights
Chesapeake to Denver flights
Chesapeake to Seattle flights
Chesapeake to Cancún flights
Chesapeake to Luis Munoz Marin Intl flights
Chesapeake to New Orleans flights
Chesapeake to Panama City flights
Chesapeake to San Diego flights
Chesapeake to Honolulu flights
Chesapeake to Punta Cana flights
Chesapeake to Cozumel flights
Chesapeake to Minneapolis flights
Chesapeake to Detroit flights
Chesapeake to Narita flights
Chesapeake to San Francisco flights
Chesapeake to Haneda flights
Chesapeake to Salt Lake City flights
Chesapeake to Charlotte flights
Chesapeake to Pensacola flights
Chesapeake to Heathrow flights
Chesapeake to Fort Myers flights
Chesapeake to Ontario flights
Chesapeake to Charleston flights
Chesapeake to Liberia flights

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 January 27, 2026.

  • What is the cheapest airport to fly out of Chesapeake?

    Istanbul airport offers the cheapest routes to Boston, 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 New York to Orlando from $27 round trip
    Fly from Las Vegas to Los Angeles from $31 round trip
    Fly from Bogotá to Medellín from $33 round trip

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