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$39+ 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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — BDL
juin 17 — juin 241
mar. 6/17
mar. 6/24
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 juin 12, 2025.

Round-trip from

$81
(Kiwi.com)

One-way from

$39
(CheapOair)
From Chesapeake to Connecticut
Search Deals
One-way flight from Chesapeake to Connecticut
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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 juin 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 6/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 8/239:49 pmORF - PVD
Nonstop1h 26mBreeze Airways
lun. 8/257:15 amPVD - ORF
Nonstop1h 32mBreeze Airways
Deal found 6/11$81
This Orbitz deal was found by Cheapflights users on 6/11. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/84:26 pmORF - HVN
Nonstop1h 20mBreeze Airways
mar. 7/159:30 amHVN - ORF
Nonstop1h 30mBreeze Airways
Deal found 6/11$92
This Priceline deal was found by Cheapflights users on 6/10. 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.
mer. 7/99:50 pmORF - BDL
Nonstop1h 25mBreeze Airways
mer. 7/167:05 amBDL - ORF
Nonstop1h 32mBreeze Airways
Deal found 6/10$92
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
dim. 6/291:01 pmORF - LGA
Nonstop1h 28mSpirit Airlines
mer. 7/96:00 amLGA - ORF
1 stop10h 25mSpirit Airlines
Deal found 6/10$160
This American Airlines deal was found by Cheapflights users on 6/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 8/226:00 amORF - JFK
Nonstop1h 20mAmerican Airlines
sam. 8/3010:30 amJFK - ORF
Nonstop1h 32mAmerican Airlines
Deal found 6/11$163
This Delta deal was found by Cheapflights users on 6/10. 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.
mer. 7/210:59 amORF - LGA
Nonstop1h 30mDelta
lun. 7/74:30 pmLGA - ORF
Nonstop1h 40mDelta
Deal found 6/10$169
This Delta deal was found by Cheapflights users on 6/10. 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.
mar. 7/17:00 amORF - JFK
Nonstop1h 22mDelta
jeu. 7/103:55 pmJFK - ORF
Nonstop1h 53mDelta
Deal found 6/10$169
This United Airlines deal was found by Cheapflights users on 6/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 7/115:27 pmORF - EWR
Nonstop1h 33mUnited Airlines
dim. 7/1310:00 pmEWR - ORF
Nonstop1h 41mUnited Airlines
Deal found 6/11$179
This American Airlines deal was found by Cheapflights users on 6/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 9/274:04 pmORF - EWR
1 stop5h 56mAmerican Airlines
dim. 9/285:00 amEWR - ORF
1 stop5h 10mAmerican Airlines
Deal found 6/12$199
This Mytrip deal was found by Cheapflights users on 6/10. 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.
lun. 6/301:51 pmORF - EWR
1 stop18h 07mSpirit Airlines
mar. 7/85:15 amEWR - ORF
1 stop13h 22mSpirit Airlines
Deal found 6/10$200
This American Airlines deal was found by Cheapflights users on 6/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 8/1410:03 amORF - LGA
Nonstop1h 26mAmerican Airlines
dim. 8/178:29 pmLGA - ORF
Nonstop1h 34mAmerican Airlines
Deal found 6/12$201
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/195:30 amORF - EWR
1 stop5h 24mDelta
sam. 8/2310:33 amEWR - ORF
2 stops7h 20mDelta
Deal found 6/11$204

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 juin 12, 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

sam. 8/23

9:49 pm-11:15 pm

Nonstop1h 26m

Providence-TFGreen

lun. 8/25

7:15 am-8:47 am

Nonstop1h 32m

$81

NorfolkNew Haven

ORF - HVN

ORFHVN

Norfolk

mar. 7/8

4:26 pm-5:46 pm

Nonstop1h 20m

Tweed-New Haven

mar. 7/15

9:30 am-11:00 am

Nonstop1h 30m

$92

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

mer. 7/9

9:50 pm-11:15 pm

Nonstop1h 25m

Hartford Bradley Intl

mer. 7/16

7:05 am-8:37 am

Nonstop1h 32m

$92

NorfolkNew York

ORF - LGA

ORFLGA

Norfolk

dim. 6/29

1:01 pm-2:29 pm

Nonstop1h 28m

New York LaGuardia

mer. 7/9

6:00 am-4:25 pm

1 stop10h 25m

$160

NorfolkNew York

ORF - JFK

ORFJFK

Norfolk

ven. 8/22

6:00 am-7:20 am

Nonstop1h 20m

New York John F Kennedy Intl

sam. 8/30

10:30 am-12:02 pm

Nonstop1h 32m

$163

NorfolkNew York

ORF - LGA

ORFLGA

Norfolk

mer. 7/2

10:59 am-12:29 pm

Nonstop1h 30m

New York LaGuardia

mar. 7/8

12:59 pm-2:30 pm

Nonstop1h 31m

$169

NorfolkNew York

ORF - JFK

ORFJFK

Norfolk

mar. 7/1

7:00 am-8:22 am

Nonstop1h 22m

New York John F Kennedy Intl

jeu. 7/10

3:55 pm-5:48 pm

Nonstop1h 53m

$169

NorfolkNewark

ORF - EWR

ORFEWR

Norfolk

ven. 7/11

5:27 pm-7:00 pm

Nonstop1h 33m

Newark

dim. 7/13

10:00 pm-11:41 pm

Nonstop1h 41m

$179

NorfolkNewark

ORF - EWR

ORFEWR

Norfolk

mar. 8/19

5:30 am-10:54 am

1 stop5h 24m

Newark

sam. 8/23

6:35 pm-12:22 am

1 stop5h 47m

$199

NorfolkNewark

ORF - EWR

ORFEWR

Norfolk

lun. 6/30

1:51 pm-7:58 am

1 stop18h 07m

Newark

mar. 7/8

5:15 am-6:37 pm

1 stop13h 22m

$200

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

Showing 1-10 of 59 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 juin 12, 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.

Rainfall in Connecticut by month

Plan your trip to Connecticut by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Connecticut ranges from 3.1 - 4.1 inches per month. September is typically the wettest month, when rainfall can reach 4.1 in. February is typically the driest time to visit Connecticut when rainfall is around 3.1 in.

Temperature in Connecticut by month

Plan your trip to Connecticut by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Connecticut, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 24.8 F).

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 juin 12, 2025.
See what other customers who have flown with Breeze Airways, Alaska Airlines and Southwest from Chesapeake to Connecticut have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Crew

8.8

Entertainment

6.6

Comfort

8.2

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
178 reviews
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Crew

8.8

Entertainment

6.6

Comfort

8.2

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Alaska Airlines
8.0
Very good
10,000 reviews
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Crew

8.8

Entertainment

6.6

Comfort

8.2

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Southwest
8.0
Very good
4,287 reviews
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Crew

8.8

Entertainment

6.6

Comfort

8.2

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Delta
8.0
Very good
7,950 reviews
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Crew

8.8

Entertainment

6.6

Comfort

8.2

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
United Airlines
7.4
Good
8,790 reviews
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Crew

8.8

Entertainment

6.6

Comfort

8.2

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

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.

  • 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 $39 on Breeze Airways. Other airlines that offer cheap prices include Spirit Airlines from $60 and Delta from $115 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 $54. On average you can expect to pay $89. The most popular route, (Norfolk - New York John F Kennedy Intl), can usually be booked for $139.

  • 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.

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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 juin 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$55Average$97FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$101Average$276FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$176Average$321FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$186Average$365FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$211Average$331FlexibilityNo cancel feeOn-time63%

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