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Chesapeake

$55+ 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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — DFW
May 29 — Jun 51
Fri 5/29
Fri 6/5
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 April 29, 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

NorfolkFort Lauderdale

ORF - FLL

ORFFLL

Norfolk

Thu 6/4

6:42 pm-9:01 pm

Nonstop2h 19m

Fort Lauderdale

Sun 6/7

3:28 pm-5:39 pm

Nonstop2h 11m

$147

NorfolkFort Lauderdale

ORF - FLL

ORFFLL

Norfolk

Fri 7/24

10:09 am-12:24 pm

Nonstop2h 15m

Fort Lauderdale

Mon 7/27

7:05 am-9:13 am

Nonstop2h 08m

$207

NorfolkFort Lauderdale

ORF - FLL

ORFFLL

Norfolk

Thu 7/9

12:59 pm-11:53 pm

1 stop10h 54m

Fort Lauderdale

Mon 7/13

4:04 pm-10:48 pm

1 stop6h 44m

$227

NorfolkFort Lauderdale

ORF - FLL

ORFFLL

Norfolk

Sun 5/24

12:05 pm-2:25 pm

Nonstop2h 20m

Fort Lauderdale

Thu 5/28

9:00 am-11:13 am

Nonstop2h 13m

$227

NorfolkFort Lauderdale

ORF - FLL

ORFFLL

Norfolk

Fri 7/24

7:00 am-2:57 pm

1 stop7h 57m

Fort Lauderdale

Fri 7/31

4:04 pm-10:48 pm

1 stop6h 44m

$227

NorfolkNew York

ORF - LGA

ORFLGA

Norfolk

Fri 6/5

3:10 pm-4:38 pm

Nonstop1h 28m

New York LaGuardia

Sat 6/6

4:39 pm-6:17 pm

Nonstop1h 38m

$229

NorfolkNewark

ORF - EWR

ORFEWR

Norfolk

Thu 8/13

6:07 pm-8:00 pm

Nonstop1h 53m

Newark

Tue 8/18

9:17 pm-10:53 pm

Nonstop1h 36m

$229

NorfolkNew York

ORF - LGA

ORFLGA

Norfolk

Thu 5/28

3:10 pm-4:38 pm

Nonstop1h 28m

New York LaGuardia

Mon 6/1

9:05 pm-10:43 pm

Nonstop1h 38m

$229

NorfolkNewark

ORF - EWR

ORFEWR

Norfolk

Wed 5/27

5:50 am-7:29 am

Nonstop1h 39m

Newark

Wed 6/3

5:40 pm-7:22 pm

Nonstop1h 42m

$229

NorfolkNew York

ORF - LGA

ORFLGA

Norfolk

Wed 6/24

10:20 am-11:55 am

Nonstop1h 35m

New York LaGuardia

Mon 6/29

8:06 am-9:40 am

Nonstop1h 34m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/26

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 Dallas/Fort Worth. Price data was last updated on April 25, 2026.

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

Which airlines fly from Chesapeake?

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

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 April 29, 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, andUnited 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
4,314 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,314 reviews
Southwest
8.0
Very good
4,314 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,465 reviews
Southwest
8.0
Very good
4,314 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,680 reviews
Southwest
8.0
Very good
4,314 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,678 reviews
Southwest
8.0
Very good
4,314 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
2,970 reviews
Southwest
8.0
Very good
4,314 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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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 April 29, 2026.

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

    Istanbul airport offers the cheapest routes to Atlanta, 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.

  • 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 Frankfurt am Main to Tirana from $29 round trip
    Fly from Brussels to Budapest from $31 round trip
    Fly from Brussels to Warsaw from $32 round trip

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