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$41+ Cheap flights from Chesapeake, VA to Connecticut

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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — BDL
Jan 16 — Jan 231
Fri 1/16
Fri 1/23
1 adult, Economy
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Cheap flight deals from Chesapeake to Connecticut

Cheapest flights from Chesapeake to Connecticut
Explore the most affordable flight options available from Chesapeake to Connecticut. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 17, 2025.

This Breeze Airways deal was found by Cheapflights users on 12/15. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/299:25 pmORF - BDL
Nonstop1h 27mBreeze Airways
Mon 1/57:10 amBDL - ORF
Nonstop1h 37mBreeze Airways
Deal found 12/15$128
This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
Thu 12/258:56 pmORF - BDL
Nonstop1h 27mBreeze Airways
Sun 1/47:15 amBDL - ORF
Nonstop1h 37mBreeze Airways
Deal found 12/17$142
This CheapOair deal was found by Cheapflights users on 12/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/189:45 pmORF - PVD
Nonstop1h 26mBreeze Airways
Mon 1/57:00 amPVD - ORF
Nonstop1h 36mBreeze Airways
Deal found 12/15$143
This CheapOair deal was found by Cheapflights users on 12/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/259:45 pmORF - PVD
Nonstop1h 26mBreeze Airways
Sat 1/37:00 amPVD - ORF
Nonstop1h 36mBreeze Airways
Deal found 12/14$163
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 12/303:01 pmORF - EWR
2 stops34h 04mMultiple Airlines
Wed 1/75:23 pmEWR - ORF
1 stop25h 15mMultiple Airlines
Deal found 12/15$172
This CheapOair deal was found by Cheapflights users on 12/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1710:05 pmORF - PVD
Nonstop1h 26mBreeze Airways
Fri 12/197:00 amPVD - ORF
Nonstop1h 36mBreeze Airways
Deal found 12/15$173
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
Sat 12/2010:05 pmORF - PVD
Nonstop1h 26mBreeze Airways
Sun 12/213:11 pmPVD - ORF
Nonstop1h 36mBreeze Airways
Deal found 12/16$178
This CheapOair deal was found by Cheapflights users on 12/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1710:05 pmORF - PVD
Nonstop1h 26mBreeze Airways
Thu 12/183:11 pmPVD - ORF
Nonstop1h 36mBreeze Airways
Deal found 12/15$183
This Delta deal was found by Cheapflights users on 12/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:00 amORF - LGA
Nonstop1h 35mDelta
Mon 1/58:20 amLGA - ORF
Nonstop1h 29mDelta
Deal found 12/15$188
This CheapOair deal was found by Cheapflights users on 12/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/189:45 pmORF - PVD
Nonstop1h 26mBreeze Airways
Mon 12/227:00 amPVD - ORF
Nonstop1h 36mBreeze Airways
Deal found 12/15$193
This American Airlines deal was found by Cheapflights users on 12/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/249:05 amORF - LGA
Nonstop1h 28mAmerican Airlines
Mon 12/297:00 amLGA - ORF
Nonstop1h 26mAmerican Airlines
Deal found 12/15$196
This United Airlines deal was found by Cheapflights users on 12/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2511:41 amORF - EWR
Nonstop1h 48mUnited Airlines
Sat 1/38:29 amEWR - ORF
Nonstop1h 39mUnited Airlines
Deal found 12/15$196

Find flight deals from Chesapeake to Connecticut

Keep the following information in mind while searching for Chesapeake to Connecticut flight deals. Data was last updated December 17, 2025.

Round-trip from

$77
(Kiwi.com)

One-way from

$41
(CheapOair)

Popular in

April

Cheapest in

February

Average price

$186
From Chesapeake to Connecticut
Search Deals
One-way flight from Chesapeake to Connecticut
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($8 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chesapeake to Connecticut that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 17, 2025.
Use the filters below to find and compare flights from Chesapeake to Connecticut that are best for you.

Fly from

Chesapeake

Fly to

Connecticut

Route

Depart

Return

Price

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Thu 1/15

9:04 pm-10:31 pm

Nonstop1h 27m

Hartford Bradley Intl

Sun 1/18

7:15 am-8:53 am

Nonstop1h 38m

$88

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Thu 1/1

8:56 pm-10:23 pm

Nonstop1h 27m

Hartford Bradley Intl

Thu 1/8

7:10 am-8:48 am

Nonstop1h 38m

$108

NorfolkProvidence

ORF - PVD

ORFPVD

Norfolk

Thu 1/15

7:21 pm-8:48 pm

Nonstop1h 27m

Providence-TFGreen

Sun 1/18

8:00 am-4:50 pm

1 stop8h 50m

$115

NorfolkProvidence

ORF - PVD

ORFPVD

Norfolk

Thu 1/29

7:21 pm-8:48 pm

Nonstop1h 27m

Providence-TFGreen

Sun 2/1

8:00 am-4:50 pm

1 stop8h 50m

$118

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Mon 1/12

9:18 pm-10:45 pm

Nonstop1h 27m

Hartford Bradley Intl

Fri 1/16

7:00 am-8:38 am

Nonstop1h 38m

$118

NorfolkProvidence

ORF - PVD

ORFPVD

Norfolk

Fri 1/2

10:05 pm-11:31 pm

Nonstop1h 26m

Providence-TFGreen

Mon 1/5

7:00 am-8:36 am

Nonstop1h 36m

$128

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Mon 12/29

9:25 pm-10:52 pm

Nonstop1h 27m

Hartford Bradley Intl

Mon 1/5

7:10 am-8:47 am

Nonstop1h 37m

$128

NorfolkProvidence

ORF - PVD

ORFPVD

Norfolk

Thu 1/15

7:33 pm-4:50 pm

2 stops21h 17m

Providence-TFGreen

Sun 1/18

5:04 pm-6:41 pm

Nonstop1h 37m

$132

NorfolkProvidence

ORF - PVD

ORFPVD

Norfolk

Thu 1/29

7:33 pm-4:50 pm

2 stops21h 17m

Providence-TFGreen

Sun 2/1

5:04 pm-6:41 pm

Nonstop1h 37m

$133

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Fri 1/9

9:18 pm-10:45 pm

Nonstop1h 27m

Hartford Bradley Intl

Mon 1/12

7:00 am-8:38 am

Nonstop1h 38m

$133

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

Showing 1-10 of 60 results
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Best time to book a flight from Chesapeake to Connecticut

Have a flexible travel schedule? Discover the best time to fly to Connecticut 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.

Cheapflights Insights

Everything you need to know about your flight from Chesapeake to Connecticut

What is the cheapest month to book a flight from Chesapeake to Connecticut?

Currently, February is the cheapest month in which you can book a flight from Chesapeake to Connecticut (average of $40). Flying from Chesapeake to Connecticut in September is currently the most expensive (average of $99). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from C6E to CT?

Find hourly flight availability from Chesapeake to Connecticut. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 17, 2025.

One of the essential ways to save on airfare from Chesapeake to Connecticut is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the morning could potentially save you up to 33% on airfare.

What is the cheapest day to fly from Chesapeake to Connecticut?

Use this chart to determine the cheapest time to fly round-trip from Chesapeake to Connecticut. Price data was last updated on June 22, 2025.

Travelers seeking maximum savings on their Chesapeake to Connecticut flight should consider departing on Saturday evenings when fares are most often at their lowest. Saturday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Connecticut

Get insights into the airlines that provide service to Connecticut. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Connecticut. Reviews last updated December 17, 2025.
Get a feel of what it's like to fly with Breeze Airways, Southwest, and American Airlines from Chesapeake to Connecticut by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.2
Very good
248 reviews

Comfort

8.2

Entertainment

6.7

Boarding

8.4

Crew

8.8

Overall

8.2

Food

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Breeze Airways
8.2
Very good
248 reviews
Breeze Airways
8.2
Very good
248 reviews

Comfort

8.2

Entertainment

6.7

Boarding

8.4

Crew

8.8

Overall

8.2

Food

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Southwest
7.9
Good
4,249 reviews
Breeze Airways
8.2
Very good
248 reviews

Comfort

8.2

Entertainment

6.7

Boarding

8.4

Crew

8.8

Overall

8.2

Food

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
American Airlines
7.2
Good
11,051 reviews
Breeze Airways
8.2
Very good
248 reviews

Comfort

8.2

Entertainment

6.7

Boarding

8.4

Crew

8.8

Overall

8.2

Food

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.

Related info for your journey

Find useful and relevant information for your journey from Chesapeake to Connecticut. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chesapeake to Connecticut?

    For as low as $88, Breeze Airways can have you in Connecticut from Chesapeake in 1h 27m. Chesapeake and Connecticut are separated by a distance of 395 mi. Generally, flights for this route are nonstop.

  • What are the cheapest airlines to fly from Chesapeake to Connecticut one-way?

    One-way options have recently been found by users for as low as $41 on Breeze Airways. Other airlines that offer cheap prices include Delta from $88 and Southwest from $99 one-way.

  • What are the most popular routes from Chesapeake to Connecticut?

    Most travelers choose Norfolk - New York John F Kennedy Intl, Norfolk - New York LaGuardia or Norfolk - Newark when deciding on the best route from Chesapeake to Connecticut.

  • What are the cheapest flights from Chesapeake to Connecticut?

    The cheapest flight price from Chesapeake to Connecticut is $79. On average you can expect to pay $170. The most popular route, (Norfolk - New York John F Kennedy Intl), can usually be booked for $179.

  • Can I find deals for flights from Chesapeake to Connecticut that include hotel bookings?

    Yes. In addition to deals on Chesapeake to Connecticut flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chesapeake to Connecticut?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chesapeake to Connecticut.

  • Can I find deals for business class flights from Chesapeake to Connecticut?

    Yes. Cheapflights offers flight deals from Chesapeake to Connecticut by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chesapeake to Connecticut?

    Currently, February is the cheapest month in which you can book a flight from Chesapeake to Connecticut (average of $40). Flying from Chesapeake to Connecticut in September is currently the most expensive (average of $99). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Top 5 airlines flying from Chesapeake to Connecticut

Discover the top 5 airlines that operate flights from Chesapeake to Connecticut. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$56Average$114FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$101Average$276FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$176Average$364FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$188Average$288FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$191Average$391FlexibilityNo cancel feeOn-time69%

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