HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chesapeake

$29+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MCO
Aug 2 — Aug 91
Sat 8/2
Sat 8/9
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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 July 28, 2025.

Cheapest one-way flight

$44

Cheapest round-trip flight

$49

Cheapest airline

American Airlines

Most popular destination

Atlanta Hartsfield-Jackson (ATL)
The cheapest one-way flight from Chesapeake is currently to Hartford Bradley Intl.
Search Deals
The cheapest round-trip flight from Chesapeake is currently to Jacksonville.
Search Deals
On average, American Airlines currently has the cheapest one-way flight from Chesapeake (avg. price of $248).
Search Deals
Atlanta Hartsfield-Jackson (ATL) is currently the most popular flight destination from Chesapeake (average round-trip price of $231).
Search Deals

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 July 28, 2025.

Fri 8/291:39 pmORF - DTW
Nonstop1h 56mSpirit Airlines
Mon 9/111:05 amDTW - ORF
Nonstop1h 39mSpirit Airlines
Deal found 7/28$79
Sun 9/145:38 pmORF - MCO
Nonstop2h 10mSpirit Airlines
Sun 9/212:39 pmMCO - ORF
Nonstop2h 04mSpirit Airlines
Deal found 7/28$88
Thu 9/45:38 pmORF - MCO
Nonstop2h 10mMultiple Airlines
Sun 9/72:50 pmMCO - ORF
Nonstop2h 07mMultiple Airlines
Deal found 7/28$90
Thu 9/1112:25 pmORF - MCO
Nonstop2h 15mSouthwest
Tue 9/169:05 amMCO - ORF
Nonstop1h 55mSouthwest
Deal found 7/27$103
Thu 8/2810:02 pmORF - MCO
Nonstop2h 11mFrontier
Sun 8/316:56 pmMCO - ORF
Nonstop2h 11mFrontier
Deal found 7/26$111
Sat 10/183:27 pmORF - ATL
Nonstop1h 57mMultiple Airlines
Mon 10/209:59 amATL - ORF
1 stop6h 44mMultiple Airlines
Deal found 7/26$112
Fri 10/103:27 pmORF - ATL
Nonstop1h 57mFrontier
Mon 10/1312:47 pmATL - ORF
Nonstop1h 40mFrontier
Deal found 7/28$123
Thu 11/68:01 amORF - ATL
1 stop4h 46mSpirit Airlines
Sun 11/91:42 pmATL - ORF
1 stop10h 25mSpirit Airlines
Deal found 7/28$142
Thu 8/2810:02 pmORF - DTW
1 stop20h 43mMultiple Airlines
Mon 9/111:05 amDTW - ORF
Nonstop1h 39mMultiple Airlines
Deal found 7/28$157
Wed 9/106:15 amORF - MIA
Nonstop2h 26mAmerican Airlines
Wed 9/179:34 pmMIA - ORF
Nonstop2h 25mAmerican Airlines
Deal found 7/27$158
Sat 10/184:23 pmORF - ATL
Nonstop1h 56mDelta
Sun 10/197:30 amATL - ORF
Nonstop1h 30mDelta
Deal found 7/28$159
Mon 8/255:20 pmORF - DFW
1 stop7h 34mSpirit Airlines
Mon 9/16:45 amDFW - ORF
1 stop4h 59mSpirit Airlines
Deal found 7/28$161

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

Fly to

Orlando

Route

Depart

Return

Price

NorfolkDetroit

ORF - DTW

ORFDTW

Norfolk

Fri 8/29

1:39 pm-3:35 pm

Nonstop1h 56m

Detroit Metropolitan Wayne County

Mon 9/1

11:05 am-12:44 pm

Nonstop1h 39m

$79

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sun 9/14

5:38 pm-7:48 pm

Nonstop2h 10m

Orlando

Sun 9/21

2:39 pm-4:43 pm

Nonstop2h 04m

$88

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Thu 9/4

5:38 pm-7:48 pm

Nonstop2h 10m

Orlando

Sun 9/7

2:50 pm-4:57 pm

Nonstop2h 07m

$90

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Thu 9/11

12:25 pm-2:40 pm

Nonstop2h 15m

Orlando

Tue 9/16

9:05 am-11:00 am

Nonstop1h 55m

$103

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Thu 8/28

10:02 pm-12:13 am

Nonstop2h 11m

Orlando

Sun 8/31

6:56 pm-9:07 pm

Nonstop2h 11m

$111

NorfolkAtlanta

ORF - ATL

ORFATL

Norfolk

Sat 10/18

3:27 pm-5:24 pm

Nonstop1h 57m

Atlanta Hartsfield-Jackson

Mon 10/20

9:59 am-4:43 pm

1 stop6h 44m

$112

NorfolkAtlanta

ORF - ATL

ORFATL

Norfolk

Fri 10/10

3:27 pm-5:24 pm

Nonstop1h 57m

Atlanta Hartsfield-Jackson

Mon 10/13

12:47 pm-2:27 pm

Nonstop1h 40m

$123

NorfolkAtlanta

ORF - ATL

ORFATL

Norfolk

Thu 11/6

8:01 am-12:47 pm

1 stop4h 46m

Atlanta Hartsfield-Jackson

Sun 11/9

1:42 pm-12:07 am

1 stop10h 25m

$142

NorfolkDetroit

ORF - DTW

ORFDTW

Norfolk

Thu 8/28

10:02 pm-6:45 pm

1 stop20h 43m

Detroit Metropolitan Wayne County

Mon 9/1

11:05 am-12:44 pm

Nonstop1h 39m

$157

NorfolkMiami

ORF - MIA

ORFMIA

Norfolk

Wed 9/10

6:15 am-8:41 am

Nonstop2h 26m

Miami

Wed 9/17

9:34 pm-11:59 pm

Nonstop2h 25m

$158

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/26

Showing 1-10 of 60 results
1
2
3
...
6

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 July 25, 2025.

To ensure you get the cheapest price possible for a flight from Chesapeake, you should look to book at least 53 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, August is the cheapest month in which you can book a flight from Chesapeake (average of $43). 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 July 27, 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 Sunday at noon when fares are usually the most expensive.

Which airlines fly from Chesapeake?

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

American Airlines
American Airlines
From $131
Delta
Delta
From $88
United Airlines
United Airlines
From $150
Southwest
Southwest
From $158

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 July 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 Breeze Airways 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
4,238 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,975 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Breeze Airways
8.0
Very good
190 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Spirit Airlines
6.3
Okay
8,040 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 July 28, 2025.

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

    Istanbul airport offers the cheapest routes to Montreal, 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?

    August 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 Cartagena from $24 round trip
    Fly from Burbank to Las Vegas from $34 round trip
    Fly from Las Vegas to Santa Ana from $35 round trip

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.