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$40+ 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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — BDL
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 April 24, 2025.

Round-trip from

$79
(CheapOair)

One-way from

$41
(Priceline)
From Chesapeake to Connecticut
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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 April 24, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
Sun 9/149:47 pmORF - PVD
Nonstop1h 26mBreeze Airways
Mon 9/227:00 amPVD - ORF
Nonstop1h 36mBreeze Airways
Deal found 4/22$80
This Priceline deal was found by Cheapflights users on 4/23. 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 6/54:01 pmORF - HVN
Nonstop1h 20mBreeze Airways
Sun 6/88:00 amHVN - ORF
Nonstop1h 30mBreeze Airways
Deal found 4/23$82
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 8/289:49 amORF - BDL
Nonstop1h 25mBreeze Airways
Mon 9/17:00 amBDL - ORF
Nonstop1h 32mBreeze Airways
Deal found 4/23$91
This Priceline deal was found by Cheapflights users on 4/23. 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.
Sun 5/1111:21 amORF - BDL
1 stop7h 53mMultiple Airlines
Wed 5/147:05 amBDL - ORF
Nonstop1h 32mMultiple Airlines
Deal found 4/23$156
This United Airlines deal was found by Cheapflights users on 4/23. 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.
Tue 5/276:15 amORF - EWR
Nonstop1h 31mUnited Airlines
Sat 5/3110:05 pmEWR - ORF
Nonstop1h 39mUnited Airlines
Deal found 4/23$163
This Delta deal was found by Cheapflights users on 4/23. 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.
Fri 8/225:00 pmORF - JFK
1 stop6h 24mDelta
Sat 8/303:15 pmJFK - ORF
Nonstop1h 39mDelta
Deal found 4/23$169
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Sat 6/72:45 pmORF - LGA
Nonstop1h 30mAmerican Airlines
Wed 6/119:57 amLGA - ORF
1 stop4h 49mAmerican Airlines
Deal found 4/23$171
This Booking.com deal was found by Cheapflights users on 4/22. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/273:28 pmORF - JFK
1 stop19h 01mFrontier
Sat 5/316:15 amJFK - ORF
1 stop10h 12mFrontier
Deal found 4/22$172
This Booking.com deal was found by Cheapflights users on 4/23. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1012:13 pmORF - LGA
1 stop6h 51mSpirit Airlines
Tue 5/134:05 pmLGA - ORF
Nonstop1h 21mSpirit Airlines
Deal found 4/23$176
This Delta deal was found by Cheapflights users on 4/23. 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.
Tue 8/2610:40 amORF - LGA
Nonstop1h 34mDelta
Thu 8/284:29 pmLGA - ORF
Nonstop1h 41mDelta
Deal found 4/23$178
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Thu 6/126:00 amORF - JFK
Nonstop1h 19mAmerican Airlines
Fri 6/209:30 amJFK - ORF
Nonstop1h 34mAmerican Airlines
Deal found 4/23$179
This Frontier deal was found by Cheapflights users on 4/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/84:48 pmORF - LGA
1 stop6h 15mFrontier
Mon 5/126:30 amLGA - ORF
1 stop8h 26mFrontier
Deal found 4/23$180

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 April 24, 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

Sun 9/14

9:47 pm-11:13 pm

Nonstop1h 26m

Providence-TFGreen

Mon 9/22

7:00 am-8:36 am

Nonstop1h 36m

$79

NorfolkNew Haven

ORF - HVN

ORFHVN

Norfolk

Thu 6/5

4:01 pm-5:21 pm

Nonstop1h 20m

Tweed-New Haven

Sun 6/8

8:00 am-9:30 am

Nonstop1h 30m

$82

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Thu 8/28

9:49 am-11:14 am

Nonstop1h 25m

Hartford Bradley Intl

Mon 9/1

7:00 am-8:32 am

Nonstop1h 32m

$91

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Sun 5/11

11:21 am-7:14 pm

1 stop7h 53m

Hartford Bradley Intl

Wed 5/14

7:05 am-8:37 am

Nonstop1h 32m

$156

NorfolkNewark

ORF - EWR

ORFEWR

Norfolk

Tue 5/27

6:15 am-7:46 am

Nonstop1h 31m

Newark

Sat 5/31

10:05 pm-11:44 pm

Nonstop1h 39m

$163

NorfolkNew York

ORF - LGA

ORFLGA

Norfolk

Sat 6/7

2:45 pm-4:15 pm

Nonstop1h 30m

New York LaGuardia

Wed 6/11

9:57 am-2:46 pm

1 stop4h 49m

$171

NorfolkNew York

ORF - JFK

ORFJFK

Norfolk

Wed 6/4

7:00 am-8:21 am

Nonstop1h 21m

New York John F Kennedy Intl

Fri 6/13

9:10 pm-11:02 pm

Nonstop1h 52m

$171

NorfolkNew York

ORF - JFK

ORFJFK

Norfolk

Tue 5/27

3:28 pm-10:29 am

1 stop19h 01m

New York John F Kennedy Intl

Sat 5/31

6:15 am-4:27 pm

1 stop10h 12m

$172

NorfolkNew York

ORF - LGA

ORFLGA

Norfolk

Sat 5/10

12:13 pm-7:04 pm

1 stop6h 51m

New York LaGuardia

Tue 5/13

4:05 pm-5:26 pm

Nonstop1h 21m

$176

NorfolkNew York

ORF - LGA

ORFLGA

Norfolk

Tue 8/26

10:40 am-12:14 pm

Nonstop1h 34m

New York LaGuardia

Thu 8/28

4:29 pm-6:10 pm

Nonstop1h 41m

$178

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 58 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 June is currently the most expensive (average of $357). 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 April 24, 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 April 24, 2025.
See what other customers who have flown with Breeze Airways, Southwest and Delta 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
159 reviews

Comfort

8.2

Crew

8.8

Overall

8.1

Entertainment

6.7

Boarding

8.3

Food

6.7

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
159 reviews
Breeze Airways
8.1
Very good
159 reviews

Comfort

8.2

Crew

8.8

Overall

8.1

Entertainment

6.7

Boarding

8.3

Food

6.7

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
159 reviews

Comfort

8.2

Crew

8.8

Overall

8.1

Entertainment

6.7

Boarding

8.3

Food

6.7

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
7,920 reviews
Breeze Airways
8.1
Very good
159 reviews

Comfort

8.2

Crew

8.8

Overall

8.1

Entertainment

6.7

Boarding

8.3

Food

6.7

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
8,685 reviews
Breeze Airways
8.1
Very good
159 reviews

Comfort

8.2

Crew

8.8

Overall

8.1

Entertainment

6.7

Boarding

8.3

Food

6.7

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!
JetBlue
7.3
Good
2,924 reviews
Breeze Airways
8.1
Very good
159 reviews

Comfort

8.2

Crew

8.8

Overall

8.1

Entertainment

6.7

Boarding

8.3

Food

6.7

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 $41 on Breeze Airways. Other airlines that offer cheap prices include Frontier from $81 and American Airlines from $97 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 $46. On average you can expect to pay $93. The most popular route, (Norfolk - New York John F Kennedy Intl), 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 June is currently the most expensive (average of $357). 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$37Average$101FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$176Average$276FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$176Average$329FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$186Average$354FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$211Average$341FlexibilityNo cancel feeOn-time63%

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