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$50+ 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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — BDL
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
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 February 4, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/4. 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 2/191:17 pm
ORF
-
HVN
Nonstop1h 29m
Breeze Airways
Sun 3/13:26 pm
HVN
-
ORF
Nonstop1h 39m
Breeze Airways
Deal found 2/4$97
This Mytrip deal was found by Cheapflights users on 2/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/269:04 pm
ORF
-
BDL
Nonstop1h 27m
Breeze Airways
Sun 3/297:15 am
BDL
-
ORF
Nonstop1h 38m
Breeze Airways
Deal found 2/4$99
This CheapOair deal was found by Cheapflights users on 2/3. 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 2/191:17 pm
ORF
-
HVN
Nonstop1h 29m
Breeze Airways
Sun 2/223:26 pm
HVN
-
ORF
Nonstop1h 39m
Breeze Airways
Deal found 2/3$102
This Mytrip deal was found by Cheapflights users on 2/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2010:31 pm
ORF
-
PVD
Nonstop1h 28m
Breeze Airways
Sun 5/241:56 pm
PVD
-
ORF
Nonstop1h 33m
Breeze Airways
Deal found 2/3$106
This Mytrip deal was found by Cheapflights users on 2/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3010:30 pm
ORF
-
BDL
Nonstop1h 29m
Breeze Airways
Wed 6/37:35 am
BDL
-
ORF
Nonstop1h 31m
Breeze Airways
Deal found 2/3$110
This Mytrip deal was found by Cheapflights users on 2/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/199:04 pm
ORF
-
BDL
Nonstop1h 27m
Breeze Airways
Mon 2/237:00 am
BDL
-
ORF
Nonstop1h 38m
Breeze Airways
Deal found 2/3$111
This Mytrip deal was found by Cheapflights users on 2/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/239:18 pm
ORF
-
BDL
Nonstop1h 27m
Breeze Airways
Fri 2/277:00 am
BDL
-
ORF
Nonstop1h 38m
Breeze Airways
Deal found 2/3$113
This CheapOair deal was found by Cheapflights users on 2/3. 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 3/510:22 am
ORF
-
PVD
Nonstop1h 27m
Breeze Airways
Thu 3/128:05 am
PVD
-
ORF
Nonstop1h 37m
Breeze Airways
Deal found 2/3$117
This CheapOair deal was found by Cheapflights users on 2/1. 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 5/288:35 pm
ORF
-
PVD
Nonstop1h 28m
Breeze Airways
Fri 5/297:20 am
PVD
-
ORF
Nonstop1h 33m
Breeze Airways
Deal found 2/1$122
This Mytrip deal was found by Cheapflights users on 2/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2010:30 pm
ORF
-
BDL
Nonstop1h 29m
Breeze Airways
Sun 5/247:15 am
BDL
-
ORF
Nonstop1h 31m
Breeze Airways
Deal found 2/3$122
This Breeze Airways deal was found by Cheapflights users on 2/3. 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 5/1412:16 pm
ORF
-
HVN
Nonstop1h 23m
Breeze Airways
Sun 5/242:39 pm
HVN
-
ORF
Nonstop1h 24m
Breeze Airways
Deal found 2/3$123
This Mytrip deal was found by Cheapflights users on 2/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/37:31 pm
ORF
-
EWR
1 stop15h 26m
Spirit Airlines
Tue 3/1012:02 pm
EWR
-
ORF
1 stop6h 24m
Spirit Airlines
Deal found 2/2$125

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 February 4, 2026.

Round-trip from

$97
(Kiwi.com)

One-way from

$50
(Booking.com)

Popular in

April

Cheapest in

February

Average price

$106
From Chesapeake to Connecticut
Search Deals
One-way flight from Chesapeake to Connecticut
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($6 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 4, 2026.
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

NorfolkNew Haven

ORF - HVN

ORFHVN

Norfolk

Thu 2/19

1:17 pm-2:46 pm

Nonstop1h 29m

Tweed-New Haven

Sun 3/1

3:26 pm-5:05 pm

Nonstop1h 39m

$97

NorfolkNew Haven

ORF - HVN

ORFHVN

Norfolk

Thu 3/19

1:17 pm-2:46 pm

Nonstop1h 29m

Tweed-New Haven

Sun 3/22

3:26 pm-5:05 pm

Nonstop1h 39m

$97

NorfolkNew Haven

ORF - HVN

ORFHVN

Norfolk

Thu 2/19

1:17 pm-2:46 pm

Nonstop1h 29m

Tweed-New Haven

Sun 2/22

3:26 pm-5:05 pm

Nonstop1h 39m

$102

NorfolkNew Haven

ORF - HVN

ORFHVN

Norfolk

Thu 3/26

1:17 pm-2:46 pm

Nonstop1h 29m

Tweed-New Haven

Sun 3/29

3:26 pm-5:05 pm

Nonstop1h 39m

$102

NorfolkProvidence

ORF - PVD

ORFPVD

Norfolk

Sat 5/30

10:31 pm-11:59 pm

Nonstop1h 28m

Providence-TFGreen

Thu 6/4

1:56 pm-3:29 pm

Nonstop1h 33m

$122

NorfolkNew Haven

ORF - HVN

ORFHVN

Norfolk

Thu 5/14

12:16 pm-1:39 pm

Nonstop1h 23m

Tweed-New Haven

Sun 5/24

2:39 pm-4:03 pm

Nonstop1h 24m

$123

NorfolkProvidence

ORF - PVD

ORFPVD

Norfolk

Wed 5/27

10:31 pm-11:59 pm

Nonstop1h 28m

Providence-TFGreen

Fri 5/29

7:20 am-8:53 am

Nonstop1h 33m

$132

NorfolkProvidence

ORF - PVD

ORFPVD

Norfolk

Tue 6/16

2:16 pm-3:44 pm

Nonstop1h 28m

Providence-TFGreen

Tue 6/23

4:29 pm-6:02 pm

Nonstop1h 33m

$133

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Fri 3/20

9:18 pm-10:45 pm

Nonstop1h 27m

Hartford Bradley Intl

Sun 3/22

7:15 am-8:53 am

Nonstop1h 38m

$133

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Thu 2/19

9:04 pm-10:31 pm

Nonstop1h 27m

Hartford Bradley Intl

Mon 2/23

10:52 am-12:05 pm

1 stop25h 13m

$134

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/3

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 $43). 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 February 4, 2026.

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 afternoon tend to be the most expensive. A flight in the morning could potentially save you up to 37% on airfare.

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 February 4, 2026.
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
263 reviews

Entertainment

6.6

Comfort

8.2

Crew

8.7

Boarding

8.3

Food

6.7

Overall

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Breeze Airways
8.2
Very good
263 reviews
Breeze Airways
8.2
Very good
263 reviews

Entertainment

6.6

Comfort

8.2

Crew

8.7

Boarding

8.3

Food

6.7

Overall

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Southwest
8.0
Very good
4,274 reviews
Breeze Airways
8.2
Very good
263 reviews

Entertainment

6.6

Comfort

8.2

Crew

8.7

Boarding

8.3

Food

6.7

Overall

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
American Airlines
7.2
Good
11,220 reviews
Breeze Airways
8.2
Very good
263 reviews

Entertainment

6.6

Comfort

8.2

Crew

8.7

Boarding

8.3

Food

6.7

Overall

8.2

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.

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 $179, Breeze Airways can have you in Connecticut from Chesapeake in 1h 20m. Chesapeake and Connecticut are separated by a distance of 296 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 $44 on Breeze Airways. Other airlines that offer cheap prices include Delta from $88 and American Airlines from $90 one-way.

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

    Most travelers choose Norfolk - Newark, Norfolk - New York John F Kennedy Intl or Norfolk - New York LaGuardia 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 $138. The most popular route, (Norfolk - Newark), can usually be booked for $125.

  • 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 $43). 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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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 February 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$58Average$121FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$101Average$273FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$156Average$256FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$176Average$320FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$275Average$401FlexibilityNo cancel feeOn-time69%

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