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Connecticut

Cheap flights from Chesapeake, VA to Connecticut

RIC — BDL
Dec 5 — Dec 121
Sat 12/5
Sat 12/12
1 adult, Economy
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Find flight deals from Chesapeake to Connecticut

Popular in

February

Cheapest in

September

Average price

$250
Highest demand for flights based on searches. 17% potential increase in price ($45 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in November 2026
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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?

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 48% on airfare.

Reviews of airlines servicing Connecticut

Get a feel of what it's like to fly with Breeze Airways,Southwest, andUnited 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
324 reviews

Boarding

8.4

Comfort

8.2

Entertainment

6.8

Food

6.7

Overall

8.2

Crew

8.8

Reviews

1 / 18
10.0
Excellent

James,Oct 2026

RSW - RDU

The plane was clean and modern. The crew was excellent. The flight left early and arrived ~ 30 mintues early. As such, our bags were delayed in arriving. Food (snacks) were average.
Breeze Airways
8.2
Very good
324 reviews
Breeze Airways
8.2
Very good
324 reviews

Boarding

8.4

Comfort

8.2

Entertainment

6.8

Food

6.7

Overall

8.2

Crew

8.8

Reviews

1 / 18
10.0
Excellent

James,Oct 2026

RSW - RDU

The plane was clean and modern. The crew was excellent. The flight left early and arrived ~ 30 mintues early. As such, our bags were delayed in arriving. Food (snacks) were average.
Southwest
8.0
Very good
4,212 reviews
Breeze Airways
8.2
Very good
324 reviews

Boarding

8.4

Comfort

8.2

Entertainment

6.8

Food

6.7

Overall

8.2

Crew

8.8

Reviews

1 / 18
10.0
Excellent

James,Oct 2026

RSW - RDU

The plane was clean and modern. The crew was excellent. The flight left early and arrived ~ 30 mintues early. As such, our bags were delayed in arriving. Food (snacks) were average.
United Airlines
7.3
Good
10,463 reviews
Breeze Airways
8.2
Very good
324 reviews

Boarding

8.4

Comfort

8.2

Entertainment

6.8

Food

6.7

Overall

8.2

Crew

8.8

Reviews

1 / 18
10.0
Excellent

James,Oct 2026

RSW - RDU

The plane was clean and modern. The crew was excellent. The flight left early and arrived ~ 30 mintues early. As such, our bags were delayed in arriving. Food (snacks) were average.
American Airlines
7.0
Good
12,228 reviews
Breeze Airways
8.2
Very good
324 reviews

Boarding

8.4

Comfort

8.2

Entertainment

6.8

Food

6.7

Overall

8.2

Crew

8.8

Reviews

1 / 18
10.0
Excellent

James,Oct 2026

RSW - RDU

The plane was clean and modern. The crew was excellent. The flight left early and arrived ~ 30 mintues early. As such, our bags were delayed in arriving. Food (snacks) were average.

Related info for your journey

  • 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.

  • 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 $64 on Breeze Airways. Other airlines that offer cheap prices include United Airlines from $79 and American Airlines from $79 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 $79. On average you can expect to pay $153. The most popular route, (Norfolk - Newark), can usually be booked for $278.

  • 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 4 airlines flying from Chesapeake to Connecticut

AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$78Average$151FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$188Average$358FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$198Average$511FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$275Average$519FlexibilityNo cancel feeOn-time69%

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