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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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — BDL
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Cheap flight deals from Chesapeake to Connecticut

Keep the following information in mind while searching for Chesapeake to Connecticut flight deals. Data was last updated October 29, 2025.

Round-trip from

$77
(Kiwi.com)

One-way from

$41
(CheapOair)

Popular in

April

Cheapest in

February

Average price

$188
From Chesapeake to Connecticut
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One-way flight from Chesapeake to Connecticut
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Highest demand for flights based on searches. 3% potential increase in price ($7 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find 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 October 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/49:45 pmORF - PVD
Nonstop1h 26mBreeze Airways
Mon 12/87:00 amPVD - ORF
Nonstop1h 36mBreeze Airways
Deal found 10/28$77
This Breeze Airways deal was found by Cheapflights users on 10/28. 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.
Sat 12/610:05 pmORF - PVD
Nonstop1h 26mBreeze Airways
Sun 12/73:11 pmPVD - ORF
Nonstop1h 36mBreeze Airways
Deal found 10/28$78
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Fri 12/510:05 pmORF - PVD
Nonstop1h 26mBreeze Airways
Mon 12/87:00 amPVD - ORF
Nonstop1h 36mBreeze Airways
Deal found 10/27$81
This CheapOair deal was found by Cheapflights users on 10/27. 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 12/310:05 pmORF - PVD
Nonstop1h 26mBreeze Airways
Thu 12/43:11 pmPVD - ORF
Nonstop1h 36mBreeze Airways
Deal found 10/27$87
This CheapOair deal was found by Cheapflights users on 10/27. 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 12/119:45 pmORF - PVD
Nonstop1h 26mBreeze Airways
Sat 12/137:00 amPVD - ORF
Nonstop1h 36mBreeze Airways
Deal found 10/27$92
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Fri 11/149:25 pmORF - BDL
Nonstop1h 27mBreeze Airways
Mon 11/177:10 amBDL - ORF
Nonstop1h 37mBreeze Airways
Deal found 10/29$97
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Fri 11/141:56 pmORF - HVN
Nonstop1h 30mBreeze Airways
Mon 11/174:06 pmHVN - ORF
Nonstop1h 30mBreeze Airways
Deal found 10/28$98
This Breeze Airways deal was found by Cheapflights users on 10/29. 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.
Fri 11/2110:05 pmORF - PVD
Nonstop1h 26mBreeze Airways
Fri 11/287:00 amPVD - ORF
Nonstop1h 36mBreeze Airways
Deal found 10/29$98
This Expedia deal was found by Cheapflights users on 10/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2110:05 pmORF - PVD
Nonstop1h 26mBreeze Airways
Mon 11/247:00 amPVD - ORF
Nonstop1h 36mBreeze Airways
Deal found 10/29$100
This Priceline deal was found by Cheapflights users on 10/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/48:51 pmORF - BDL
Nonstop1h 27mBreeze Airways
Mon 12/87:10 amBDL - ORF
Nonstop1h 37mBreeze Airways
Deal found 10/28$102
This Breeze Airways deal was found by Cheapflights users on 10/27. 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.
Thu 12/118:51 pmORF - BDL
Nonstop1h 27mBreeze Airways
Thu 12/187:10 amBDL - ORF
Nonstop1h 37mBreeze Airways
Deal found 10/27$103
This Breeze Airways deal was found by Cheapflights users on 10/28. 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.
Wed 11/1910:05 pmORF - PVD
Nonstop1h 26mBreeze Airways
Fri 11/217:00 amPVD - ORF
Nonstop1h 36mBreeze Airways
Deal found 10/28$104

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 October 29, 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

NorfolkProvidence

ORF - PVD

ORFPVD

Norfolk

Sat 12/6

10:05 pm-11:31 pm

Nonstop1h 26m

Providence-TFGreen

Sun 12/7

3:11 pm-4:47 pm

Nonstop1h 36m

$78

NorfolkProvidence

ORF - PVD

ORFPVD

Norfolk

Thu 1/15

7:21 pm-8:48 pm

Nonstop1h 27m

Providence-TFGreen

Sun 1/18

5:04 pm-6:41 pm

Nonstop1h 37m

$85

NorfolkProvidence

ORF - PVD

ORFPVD

Norfolk

Wed 12/3

10:05 pm-11:31 pm

Nonstop1h 26m

Providence-TFGreen

Thu 12/4

3:11 pm-4:47 pm

Nonstop1h 36m

$87

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Fri 11/14

9:25 pm-10:52 pm

Nonstop1h 27m

Hartford Bradley Intl

Mon 11/17

7:10 am-8:47 am

Nonstop1h 37m

$97

NorfolkNew Haven

ORF - HVN

ORFHVN

Norfolk

Fri 11/14

1:56 pm-3:26 pm

Nonstop1h 30m

Tweed-New Haven

Mon 11/17

4:06 pm-5:36 pm

Nonstop1h 30m

$98

NorfolkProvidence

ORF - PVD

ORFPVD

Norfolk

Fri 11/21

10:05 pm-11:31 pm

Nonstop1h 26m

Providence-TFGreen

Fri 11/28

7:00 am-8:36 am

Nonstop1h 36m

$98

NorfolkProvidence

ORF - PVD

ORFPVD

Norfolk

Fri 11/21

10:05 pm-11:31 pm

Nonstop1h 26m

Providence-TFGreen

Mon 11/24

7:00 am-8:36 am

Nonstop1h 36m

$100

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Thu 12/4

8:51 pm-10:18 pm

Nonstop1h 27m

Hartford Bradley Intl

Mon 12/8

7:10 am-8:47 am

Nonstop1h 37m

$102

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Thu 12/11

8:51 pm-10:18 pm

Nonstop1h 27m

Hartford Bradley Intl

Thu 12/18

7:10 am-8:47 am

Nonstop1h 37m

$103

NorfolkProvidence

ORF - PVD

ORFPVD

Norfolk

Wed 11/19

10:05 pm-11:31 pm

Nonstop1h 26m

Providence-TFGreen

Fri 11/21

7:00 am-8:36 am

Nonstop1h 36m

$104

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

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 October 29, 2025.

One of the essential ways to save on airfare from Chesapeake to Connecticut is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the afternoon could potentially save you up to 35% 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 October 29, 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
8.1
Very good
221 reviews

Entertainment

6.6

Comfort

8.2

Boarding

8.3

Overall

8.1

Crew

8.7

Food

6.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Breeze Airways
8.1
Very good
221 reviews
Breeze Airways
8.1
Very good
221 reviews

Entertainment

6.6

Comfort

8.2

Boarding

8.3

Overall

8.1

Crew

8.7

Food

6.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Southwest
8.0
Very good
4,241 reviews
Breeze Airways
8.1
Very good
221 reviews

Entertainment

6.6

Comfort

8.2

Boarding

8.3

Overall

8.1

Crew

8.7

Food

6.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
American Airlines
7.2
Good
11,032 reviews
Breeze Airways
8.1
Very good
221 reviews

Entertainment

6.6

Comfort

8.2

Boarding

8.3

Overall

8.1

Crew

8.7

Food

6.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!

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 $78, Breeze Airways can have you in Connecticut from Chesapeake in 1h 26m. Chesapeake and Connecticut are separated by a distance of 420 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 Spirit Airlines from $81 and Frontier from $81 one-way.

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

    Most travelers choose Norfolk - New York LaGuardia, Norfolk - New York John F Kennedy Intl 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 $78. On average you can expect to pay $168. The most popular route, (Norfolk - New York LaGuardia), can usually be booked for $157.

  • 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.

See more FAQs

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Alternative routes for Chesapeake to Connecticut

See prices for flight routes from nearby airports that may be better suited for you.
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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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$56Average$113FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$101Average$276FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$176Average$364FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$188Average$327FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$191Average$391FlexibilityNo cancel feeOn-time69%

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