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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 6/6. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — MCO
Jun 13 — Jun 201
Sat 6/13
Sat 6/20
1 adult, Economy
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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 May 14, 2026. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

NorfolkAtlanta

ORF - ATL

ORFATL

Norfolk

Fri 6/19

6:20 am-8:07 am

Nonstop1h 47m

Atlanta Hartsfield-Jackson

Tue 6/23

9:50 am-11:34 am

Nonstop1h 44m

$119

NorfolkAtlanta

ORF - ATL

ORFATL

Norfolk

Thu 6/11

4:30 pm-10:15 pm

1 stop5h 45m

Atlanta Hartsfield-Jackson

Thu 8/6

9:05 am-12:30 pm

1 stop3h 25m

$146

NorfolkAtlanta

ORF - ATL

ORFATL

Norfolk

Fri 7/3

3:30 pm-10:40 pm

2 stops7h 10m

Atlanta Hartsfield-Jackson

Tue 7/7

10:20 am-2:25 pm

1 stop4h 05m

$240

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Thu 8/20

10:20 am-5:47 pm

1 stop7h 27m

Orlando

Sat 8/29

9:05 am-3:29 pm

1 stop6h 24m

$253

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Mon 9/14

6:05 pm-1:00 am

1 stop6h 55m

Orlando

Thu 9/17

6:15 am-11:36 am

1 stop5h 21m

$253

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Tue 11/3

8:00 am-4:55 pm

2 stops8h 55m

Orlando

Tue 11/10

6:35 am-5:20 pm

2 stops10h 45m

$269

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Fri 6/12

5:35 am-1:55 pm

1 stop8h 20m

Orlando

Wed 6/17

9:45 am-11:45 am

Nonstop2h 00m

$272

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Thu 7/2

4:30 pm-12:30 am

2 stops8h 00m

Orlando

Tue 7/7

8:00 am-12:00 pm

1 stop4h 00m

$287

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Wed 6/24

3:40 pm-9:05 pm

1 stop5h 25m

Orlando

Fri 7/3

7:05 am-3:05 pm

2 stops8h 00m

$287

NorfolkAtlanta

ORF - ATL

ORFATL

Norfolk

Tue 6/16

3:40 pm-9:00 pm

1 stop5h 20m

Atlanta Hartsfield-Jackson

Thu 6/18

7:40 am-3:05 pm

2 stops7h 25m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/10

Showing 1-10 of 60 resultsSorted by cheapest first
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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 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 May 9, 2026.

Those who are seeking the cheapest fare on flights departing from Chesapeake would be wise to consider leaving during Wednesday at noon when prices are typically at their lowest. When considering other options, price-conscious travelers should avoid Saturday 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, Frontier, Southwest, Breeze Airways, American Airlines. These airlines depart to the following popular destinations: Orlando.

American Airlines
American Airlines
From $158
Delta
Delta
From $88
United Airlines
United Airlines
From $128
Breeze Airways
Breeze Airways
From $56

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 May 14, 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 Breeze Airways,Southwest, andAmerican 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.
Breeze Airways
8.1
Very good
284 reviews

Overall

8.1

Food

6.7

Comfort

8.2

Entertainment

6.7

Boarding

8.3

Crew

8.7

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Breeze Airways
8.1
Very good
284 reviews
Breeze Airways
8.1
Very good
284 reviews

Overall

8.1

Food

6.7

Comfort

8.2

Entertainment

6.7

Boarding

8.3

Crew

8.7

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Southwest
8.0
Very good
4,298 reviews
Breeze Airways
8.1
Very good
284 reviews

Overall

8.1

Food

6.7

Comfort

8.2

Entertainment

6.7

Boarding

8.3

Crew

8.7

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
American Airlines
7.1
Good
11,666 reviews
Breeze Airways
8.1
Very good
284 reviews

Overall

8.1

Food

6.7

Comfort

8.2

Entertainment

6.7

Boarding

8.3

Crew

8.7

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Spirit Airlines
6.3
Okay
8,629 reviews
Breeze Airways
8.1
Very good
284 reviews

Overall

8.1

Food

6.7

Comfort

8.2

Entertainment

6.7

Boarding

8.3

Crew

8.7

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Frontier
5.7
Fair
2,953 reviews
Breeze Airways
8.1
Very good
284 reviews

Overall

8.1

Food

6.7

Comfort

8.2

Entertainment

6.7

Boarding

8.3

Crew

8.7

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.

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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 May 14, 2026.

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

    Medellín Jose Maria Cordova Intl airport offers the cheapest routes to Panama City, from $21; whereas Istanbul airport is typically cheaper if you're flying to Atlanta, from $23. It's best to make sure you are flexible on dates to find the cheapest possible flight options for your journey.

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

    Check out the cheapest flights from Chesapeake to embark to:
    Fly from Medellín to Santa Marta from $21 round trip
    Fly from Medellín to Cartagena from $23 round trip
    Fly from Istanbul to Ankara from $23 round trip
    Fly from Cheongju to Jeju City from $24 round trip
    Fly from Cartagena to Bogotá from $25 round trip

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