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Connecticut

$58+ 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 7/22. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — BDL
Jul 19 — Jul 261
Sun 7/19
Sun 7/26
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 June 19, 2026.

This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Wed 8/2610:30 pm
ORF
-
BDL
Nonstop1h 29m
Breeze Airways
Sun 8/308:00 am
BDL
-
ORF
Nonstop1h 31m
Breeze Airways
Deal found 6/15$91
This Kiwi.com deal was found by Cheapflights users on 6/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:11 pm
ORF
-
HVN
Nonstop1h 23m
Breeze Airways
Sun 8/302:34 pm
HVN
-
ORF
Nonstop1h 24m
Breeze Airways
Deal found 6/14$97
This Breeze Airways deal was found by Cheapflights users on 6/19. 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 7/110:30 pm
ORF
-
BDL
Nonstop1h 29m
Breeze Airways
Wed 7/87:35 am
BDL
-
ORF
Nonstop1h 31m
Breeze Airways
Deal found 6/19$133
This CheapOair deal was found by Cheapflights users on 6/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/179:25 pm
ORF
-
PVD
Nonstop1h 27m
Breeze Airways
Sat 9/197:00 am
PVD
-
ORF
Nonstop1h 37m
Breeze Airways
Deal found 6/17$142
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Wed 7/810:31 pm
ORF
-
PVD
Nonstop1h 28m
Breeze Airways
Wed 7/157:35 am
PVD
-
ORF
Nonstop1h 33m
Breeze Airways
Deal found 6/16$147
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 7/410:30 pm
ORF
-
BDL
Nonstop1h 29m
Breeze Airways
Sun 7/58:00 am
BDL
-
ORF
Nonstop1h 31m
Breeze Airways
Deal found 6/18$147
This Breeze Airways deal was found by Cheapflights users on 6/16. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/179:25 pm
ORF
-
PVD
Nonstop1h 27m
Breeze Airways
Sun 9/202:40 pm
PVD
-
ORF
Nonstop1h 37m
Breeze Airways
Deal found 6/16$148
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Thu 7/212:11 pm
ORF
-
HVN
Nonstop1h 23m
Breeze Airways
Sun 7/52:34 pm
HVN
-
ORF
Nonstop1h 24m
Breeze Airways
Deal found 6/15$152
This Expedia deal was found by Cheapflights users on 6/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1510:31 pm
ORF
-
PVD
Nonstop1h 28m
Breeze Airways
Wed 7/227:35 am
PVD
-
ORF
Nonstop1h 33m
Breeze Airways
Deal found 6/15$152
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Sat 7/1110:30 pm
ORF
-
BDL
Nonstop1h 29m
Breeze Airways
Fri 7/176:00 am
BDL
-
ORF
Nonstop1h 31m
Breeze Airways
Deal found 6/17$152
This Breeze Airways deal was found by Cheapflights users on 6/17. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/2312:11 pm
ORF
-
HVN
Nonstop1h 23m
Breeze Airways
Sun 7/262:34 pm
HVN
-
ORF
Nonstop1h 24m
Breeze Airways
Deal found 6/17$153
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Mon 7/1310:08 pm
ORF
-
PVD
Nonstop1h 28m
Breeze Airways
Wed 7/227:35 am
PVD
-
ORF
Nonstop1h 33m
Breeze Airways
Deal found 6/16$153

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 June 19, 2026.

Round-trip from

$91
(Kiwi.com)

One-way from

$58
(Kiwi.com)

Popular in

February

Cheapest in

November

Average price

$189
From Chesapeake to Connecticut
Search Deals
One-way flight from Chesapeake to Connecticut
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 19, 2026.
Use the filters below to find and compare flights from Chesapeake to Connecticut that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Wed 7/1

10:30 pm-11:59 pm

Nonstop1h 29m

Hartford Bradley Intl

Wed 7/8

7:35 am-9:06 am

Nonstop1h 31m

$138

NorfolkProvidence

ORF - PVD

ORFPVD

Norfolk

Wed 7/15

10:31 pm-11:59 pm

Nonstop1h 28m

Providence-TFGreen

Wed 7/22

7:35 am-9:08 am

Nonstop1h 33m

$148
Quickest round-trip

NorfolkNew Haven

ORF - HVN

ORFHVN

Norfolk

Thu 7/23

12:11 pm-1:34 pm

Nonstop1h 23m

Tweed-New Haven

Sun 7/26

2:34 pm-3:58 pm

Nonstop1h 24m

$153

NorfolkNew Haven

ORF - HVN

ORFHVN

Norfolk

Thu 7/16

12:11 pm-1:34 pm

Nonstop1h 23m

Tweed-New Haven

Sun 7/19

2:34 pm-3:58 pm

Nonstop1h 24m

$157

NorfolkNew Haven

ORF - HVN

ORFHVN

Norfolk

Thu 7/2

12:11 pm-1:34 pm

Nonstop1h 23m

Tweed-New Haven

Thu 7/2

2:34 pm-3:58 pm

Nonstop1h 24m

$158

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Wed 7/15

10:30 pm-11:59 pm

Nonstop1h 29m

Hartford Bradley Intl

Sun 7/19

8:00 am-9:31 am

Nonstop1h 31m

$158

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Sun 7/12

10:11 am-11:40 am

Nonstop1h 29m

Hartford Bradley Intl

Thu 7/16

8:00 am-9:31 am

Nonstop1h 31m

$163

NorfolkProvidence

ORF - PVD

ORFPVD

Norfolk

Fri 8/14

10:08 pm-11:36 pm

Nonstop1h 28m

Providence-TFGreen

Tue 8/18

4:29 pm-6:02 pm

Nonstop1h 33m

$173

NorfolkProvidence

ORF - PVD

ORFPVD

Norfolk

Wed 8/19

10:31 pm-11:59 pm

Nonstop1h 28m

Providence-TFGreen

Mon 8/24

7:20 am-8:53 am

Nonstop1h 33m

$173

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Sat 7/18

10:30 pm-11:59 pm

Nonstop1h 29m

Hartford Bradley Intl

Mon 7/20

6:00 am-7:31 am

Nonstop1h 31m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

Showing 1-10 of 60 resultsSorted by cheapest first
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6

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 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 June 19, 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 47% on airfare.

How much does it cost to fly round-trip from Chesapeake to Connecticut?

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 June 19, 2026.
Get a feel of what it's like to fly with Breeze Airways,Southwest, andAmerican 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
291 reviews

Boarding

8.3

Comfort

8.2

Crew

8.8

Overall

8.2

Entertainment

6.6

Food

6.7

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Breeze Airways
8.2
Very good
291 reviews
Breeze Airways
8.2
Very good
291 reviews

Boarding

8.3

Comfort

8.2

Crew

8.8

Overall

8.2

Entertainment

6.6

Food

6.7

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Southwest
7.9
Good
4,239 reviews
Breeze Airways
8.2
Very good
291 reviews

Boarding

8.3

Comfort

8.2

Crew

8.8

Overall

8.2

Entertainment

6.6

Food

6.7

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
American Airlines
7.1
Good
11,699 reviews
Breeze Airways
8.2
Very good
291 reviews

Boarding

8.3

Comfort

8.2

Crew

8.8

Overall

8.2

Entertainment

6.6

Food

6.7

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.

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 popular is this Chesapeake to Connecticut flight route?

    Within the past month, 1 users have taken a look at flights from Chesapeake to Connecticut.

  • How long is the flight from Chesapeake to Connecticut?

    For as low as $138, Breeze Airways can have you in Connecticut from Chesapeake in 1h 29m. 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 $49 on Breeze Airways. Other airlines that offer cheap prices include United Airlines from $79 and American Airlines from $88 one-way.

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

    Most travelers choose Norfolk - New York John F Kennedy Intl, Norfolk - Newark 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 $67. On average you can expect to pay $150. The most popular route, (Norfolk - New York John F Kennedy Intl), can usually be booked for $239.

  • 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.

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 June 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$78Average$150FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$109Average$273FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$156Average$308FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$196Average$425FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$288Average$468FlexibilityNo cancel feeOn-time69%

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