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Chesapeake

$54+ 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 11/3. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — ORD
Jul 13 — Jul 201
Mon 7/13
Mon 7/20
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 June 13, 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

Sat 9/19

8:00 am-5:15 pm

1 stop9h 15m

Fort Lauderdale

Wed 9/23

7:00 am-12:15 pm

1 stop5h 15m

$171

NorfolkFort Lauderdale

ORF - FLL

ORFFLL

Norfolk

Sat 8/15

7:06 pm-10:58 pm

1 stop3h 52m

Fort Lauderdale

Mon 8/24

4:04 pm-11:08 pm

1 stop7h 04m

$194

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sat 7/18

7:00 am-9:20 am

Nonstop2h 20m

Orlando

Wed 7/22

7:27 pm-9:45 pm

Nonstop2h 18m

$203

NorfolkFort Lauderdale

ORF - FLL

ORFFLL

Norfolk

Wed 8/5

12:15 pm-8:25 pm

2 stops8h 10m

Fort Lauderdale

Wed 8/19

7:00 am-11:35 am

1 stop4h 35m

$204

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Thu 8/13

7:59 pm-11:59 pm

1 stop4h 00m

Boston Logan Intl

Sat 8/15

5:45 am-9:34 am

1 stop3h 49m

$207

NorfolkOrlando

ORF - MCO

ORFMCO

Norfolk

Sun 7/19

7:00 am-9:12 am

Nonstop2h 12m

Orlando

Wed 7/22

7:27 pm-9:45 pm

Nonstop2h 18m

$218

NorfolkBoston

ORF - BOS

ORFBOS

Norfolk

Tue 9/8

6:00 pm-7:43 pm

Nonstop1h 43m

Boston Logan Intl

Mon 9/14

4:15 pm-6:10 pm

Nonstop1h 55m

$222

NorfolkFort Lauderdale

ORF - FLL

ORFFLL

Norfolk

Tue 8/11

6:00 am-8:15 am

Nonstop2h 15m

Fort Lauderdale

Wed 8/19

6:45 pm-9:02 pm

Nonstop2h 17m

$227

NorfolkFort Lauderdale

ORF - FLL

ORFFLL

Norfolk

Sat 10/24

7:00 am-4:11 pm

1 stop9h 11m

Fort Lauderdale

Sat 10/31

7:00 am-6:03 pm

1 stop11h 03m

$227

NorfolkFort Lauderdale

ORF - FLL

ORFFLL

Norfolk

Sat 7/11

7:06 pm-10:58 pm

1 stop3h 52m

Fort Lauderdale

Sat 7/18

2:39 pm-6:26 pm

1 stop3h 47m

$236

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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.

Which airlines fly from Chesapeake?

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

American Airlines
American Airlines
From $152
Delta
Delta
From $88
United Airlines
United Airlines
From $126
Breeze Airways
Breeze Airways
From $56

When is the cheapest time to fly from Chesapeake?

Use this chart to determine the cheapest time to fly round-trip from Chesapeake to O'Hare Intl. Price data was last updated on June 8, 2026.

Those who are seeking the cheapest fare on flights departing from Chesapeake would be wise to consider leaving during Wednesday evenings when prices are typically at their lowest. When considering other options, price-conscious travelers should avoid Saturday evenings 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 June 13, 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 United Airlines,American Airlines, andFrontier 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.
United Airlines
7.4
Good
9,819 reviews

Boarding

7.7

Food

6.6

Crew

8.1

Entertainment

7.1

Overall

7.4

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
United Airlines
7.4
Good
9,819 reviews
United Airlines
7.4
Good
9,819 reviews

Boarding

7.7

Food

6.6

Crew

8.1

Entertainment

7.1

Overall

7.4

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
American Airlines
7.1
Good
11,651 reviews
United Airlines
7.4
Good
9,819 reviews

Boarding

7.7

Food

6.6

Crew

8.1

Entertainment

7.1

Overall

7.4

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
Frontier
5.6
Fair
2,892 reviews
United Airlines
7.4
Good
9,819 reviews

Boarding

7.7

Food

6.6

Crew

8.1

Entertainment

7.1

Overall

7.4

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.

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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 June 13, 2026.

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

    Barranquilla E Cortissoz airport offers the cheapest routes to New York, from $20; 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 Barranquilla to Medellín from $20 round trip
    Fly from Istanbul to Ankara from $23 round trip
    Fly from Medellín to Santa Marta from $24 round trip
    Fly from Cheongju to Jeju City from $24 round trip
    Fly from Bogotá to Cartagena from $27 round trip

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