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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 11/27. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — BDL
Oct 14 — Oct 211
Tue 10/14
Tue 10/21
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 September 14, 2025.

Round-trip from

$82
(Priceline)

One-way from

$41
(CheapOair)

Popular in

April

Cheapest in

February

Average price

$196
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. 2% potential increase in price ($3 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 September 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 September 14, 2025.

This Priceline deal was found by Cheapflights users on 9/11. 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.
Sat 9/2710:05 pmORF - PVD
Nonstop1h 26mBreeze Airways
Wed 10/17:00 amPVD - ORF
Nonstop1h 36mBreeze Airways
Deal found 9/11$82
This Breeze Airways deal was found by Cheapflights users on 9/12. 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 10/110:05 pmORF - PVD
Nonstop1h 26mBreeze Airways
Mon 10/67:00 amPVD - ORF
Nonstop1h 36mBreeze Airways
Deal found 9/12$99
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2910:05 pmORF - PVD
Nonstop1h 26mBreeze Airways
Fri 10/37:00 amPVD - ORF
Nonstop1h 36mBreeze Airways
Deal found 9/14$102
This Breeze Airways deal was found by Cheapflights users on 9/14. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/103:56 pmORF - HVN
Nonstop1h 30mBreeze Airways
Mon 10/134:06 pmHVN - ORF
Nonstop1h 30mBreeze Airways
Deal found 9/14$103
This Breeze Airways deal was found by Cheapflights users on 9/12. 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 9/12$103
This Breeze Airways deal was found by Cheapflights users on 9/13. 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 9/2710:05 pmORF - PVD
Nonstop1h 26mBreeze Airways
Thu 10/23:15 pmPVD - ORF
Nonstop1h 36mBreeze Airways
Deal found 9/13$104
This Breeze Airways deal was found by Cheapflights users on 9/14. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/31:56 pmORF - HVN
Nonstop1h 30mBreeze Airways
Mon 10/64:06 pmHVN - ORF
Nonstop1h 30mBreeze Airways
Deal found 9/14$113
This Breeze Airways deal was found by Cheapflights users on 9/12. 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 10/29:49 pmORF - PVD
Nonstop1h 26mBreeze Airways
Mon 10/67:00 amPVD - ORF
Nonstop1h 36mBreeze Airways
Deal found 9/12$114
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 11/209:45 pmORF - PVD
Nonstop1h 26mBreeze Airways
Thu 11/273:11 pmPVD - ORF
Nonstop1h 36mBreeze Airways
Deal found 9/14$119
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/294:57 pmORF - HVN
Nonstop1h 30mBreeze Airways
Fri 10/34:06 pmHVN - ORF
Nonstop1h 30mBreeze Airways
Deal found 9/14$120
This CheapOair deal was found by Cheapflights users on 9/12. 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.
Fri 10/2410:05 pmORF - PVD
Nonstop1h 26mBreeze Airways
Mon 10/277:00 amPVD - ORF
Nonstop1h 36mBreeze Airways
Deal found 9/12$122
This Breeze Airways deal was found by Cheapflights users on 9/12. 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 9/1510:05 pmORF - PVD
Nonstop1h 26mBreeze Airways
Wed 9/177:00 amPVD - ORF
Nonstop1h 36mBreeze Airways
Deal found 9/12$128

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 September 14, 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 9/27

10:05 pm-11:31 pm

Nonstop1h 26m

Providence-TFGreen

Wed 10/1

7:00 am-8:36 am

Nonstop1h 36m

$82

NorfolkNew Haven

ORF - HVN

ORFHVN

Norfolk

Fri 10/10

3:56 pm-5:26 pm

Nonstop1h 30m

Tweed-New Haven

Mon 10/13

4:06 pm-5:36 pm

Nonstop1h 30m

$103

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

Sat 9/27

10:05 pm-11:31 pm

Nonstop1h 26m

Providence-TFGreen

Thu 10/2

3:15 pm-4:51 pm

Nonstop1h 36m

$104

NorfolkProvidence

ORF - PVD

ORFPVD

Norfolk

Thu 10/30

9:49 pm-11:15 pm

Nonstop1h 26m

Providence-TFGreen

Sat 11/1

7:00 am-8:36 am

Nonstop1h 36m

$104

NorfolkProvidence

ORF - PVD

ORFPVD

Norfolk

Mon 9/29

10:05 pm-11:31 pm

Nonstop1h 26m

Providence-TFGreen

Thu 10/2

3:15 pm-4:51 pm

Nonstop1h 36m

$108

NorfolkNew Haven

ORF - HVN

ORFHVN

Norfolk

Fri 10/3

1:56 pm-3:26 pm

Nonstop1h 30m

Tweed-New Haven

Mon 10/6

4:06 pm-5:36 pm

Nonstop1h 30m

$113

NorfolkProvidence

ORF - PVD

ORFPVD

Norfolk

Thu 10/2

9:49 pm-11:15 pm

Nonstop1h 26m

Providence-TFGreen

Mon 10/6

7:00 am-8:36 am

Nonstop1h 36m

$114

NorfolkNew Haven

ORF - HVN

ORFHVN

Norfolk

Mon 9/29

4:57 pm-6:27 pm

Nonstop1h 30m

Tweed-New Haven

Fri 10/3

4:06 pm-5:36 pm

Nonstop1h 30m

$120

NorfolkNew Haven

ORF - HVN

ORFHVN

Norfolk

Mon 9/29

5:38 pm-1:57 pm

1 stop20h 19m

Tweed-New Haven

Fri 10/3

4:06 pm-5:36 pm

Nonstop1h 30m

$154

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

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, November is the cheapest month in which you can book a flight from Chesapeake to Connecticut (average of $287). Flying from Chesapeake to Connecticut in December is currently the most expensive (average of $351). 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 September 14, 2025.

When flying from Chesapeake to Connecticut, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 September 14, 2025.
Get a feel of what it's like to fly with Southwest, Breeze Airways, and United 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.
Southwest
8.0
Very good
4,245 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Breeze Airways
8.0
Very good
205 reviews
Southwest
8.0
Very good
4,245 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,931 reviews
Southwest
8.0
Very good
4,245 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,245 reviews

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 22m. Chesapeake and Connecticut are separated by a distance of 296 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 Frontier from $72 and Southwest from $77 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 $39. On average you can expect to pay $124. The most popular route, (Norfolk - New York LaGuardia), can usually be booked for $159.

  • 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, November is the cheapest month in which you can book a flight from Chesapeake to Connecticut (average of $287). Flying from Chesapeake to Connecticut in December is currently the most expensive (average of $351). 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 September 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$56Average$111FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$101Average$276FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$176Average$344FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$188Average$327FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$196Average$345FlexibilityNo cancel feeOn-time71%

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