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$36+ 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 5/21. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — BDL
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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Cheap flight deals from Chesapeake to Connecticut

Discover tips and strategies to find the most affordable flight options for your journey from Chesapeake (C6E) to Connecticut (USCT). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$55
(Mytrip)

One-way from

$36
(Mytrip)
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 January 21, 2025.

This Mytrip deal was found by Cheapflights users on 1/21. 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.
Thu 2/63:00 pmORF - HVN
Nonstop1h 20mBreeze Airways
Sun 2/97:15 amHVN - ORF
Nonstop1h 30mBreeze Airways
Deal found 1/21$55
This Mytrip deal was found by Cheapflights users on 1/21. 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.
Fri 1/319:14 pmORF - BDL
Nonstop1h 26mBreeze Airways
Sun 2/27:05 amBDL - ORF
Nonstop1h 34mBreeze Airways
Deal found 1/21$75
This Gotogate deal was found by Cheapflights users on 1/21. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/138:00 amORF - PVD
Nonstop1h 27mBreeze Airways
Sun 3/1610:07 amPVD - ORF
Nonstop1h 32mBreeze Airways
Deal found 1/21$76
This Frontier deal was found by Cheapflights users on 1/21. 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.
Tue 3/43:37 pmORF - EWR
1 stop5h 33mFrontier
Wed 3/510:10 pmEWR - ORF
1 stop10h 28mFrontier
Deal found 1/21$110
This CheapOair deal was found by Cheapflights users on 1/20. 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.
Sat 2/158:58 amORF - EWR
1 stop12h 02mMultiple Airlines
Wed 2/196:25 amEWR - ORF
1 stop9h 07mMultiple Airlines
Deal found 1/20$140
This United Airlines deal was found by Cheapflights users on 1/21. 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.
Wed 4/26:00 amORF - EWR
Nonstop1h 37mUnited Airlines
Tue 4/811:12 amEWR - ORF
Nonstop1h 36mUnited Airlines
Deal found 1/21$163
This CheapOair deal was found by Cheapflights users on 1/21. 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 2/610:57 amORF - EWR
1 stop11h 03mSpirit Airlines
Tue 2/116:41 pmEWR - ORF
1 stop20h 51mSpirit Airlines
Deal found 1/21$165
This American Airlines deal was found by Cheapflights users on 1/20. 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.
Fri 2/285:45 amORF - LGA
Nonstop1h 35mAmerican Airlines
Sun 3/210:30 amLGA - ORF
Nonstop1h 23mAmerican Airlines
Deal found 1/20$179
This Delta deal was found by Cheapflights users on 1/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/203:27 pmORF - JFK
Nonstop1h 24mDelta
Sun 2/239:20 pmJFK - ORF
Nonstop1h 32mDelta
Deal found 1/19$179
This CheapOair deal was found by Cheapflights users on 1/21. 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 2/284:29 pmORF - LGA
1 stop6h 20mMultiple Airlines
Mon 3/35:59 pmLGA - ORF
1 stop23h 35mMultiple Airlines
Deal found 1/21$182
This Delta deal was found by Cheapflights users on 1/21. 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.
Wed 4/21:15 pmORF - EWR
1 stop7h 15mDelta
Tue 4/85:56 pmEWR - ORF
1 stop6h 07mDelta
Deal found 1/21$183
This American Airlines deal was found by Cheapflights users on 1/21. 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.
Fri 2/285:35 amORF - JFK
Nonstop1h 30mAmerican Airlines
Mon 3/39:45 pmJFK - ORF
Nonstop1h 29mAmerican Airlines
Deal found 1/21$186

Find flights from Chesapeake to Connecticut within your budget

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

NorfolkNew Haven

ORF - HVN

ORFHVN

Norfolk

Thu 2/6

3:00 pm-4:20 pm

Nonstop1h 20m

Tweed-New Haven

Sun 2/9

7:15 am-8:45 am

Nonstop1h 30m

$55

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

Fri 1/31

9:14 pm-10:40 pm

Nonstop1h 26m

Hartford Bradley Intl

Sun 2/2

7:05 am-8:39 am

Nonstop1h 34m

$75

NorfolkProvidence

ORF - PVD

ORFPVD

Norfolk

Thu 3/13

8:00 am-9:27 am

Nonstop1h 27m

Providence-TFGreen

Sun 3/16

10:07 am-11:39 am

Nonstop1h 32m

$76

NorfolkNewark

ORF - EWR

ORFEWR

Norfolk

Tue 3/4

3:37 pm-9:10 pm

1 stop5h 33m

Newark

Wed 3/5

10:10 pm-8:38 am

1 stop10h 28m

$110

NorfolkNewark

ORF - EWR

ORFEWR

Norfolk

Sat 2/15

8:58 am-9:00 pm

1 stop12h 02m

Newark

Wed 2/19

6:25 am-3:32 pm

1 stop9h 07m

$140

NorfolkNewark

ORF - EWR

ORFEWR

Norfolk

Wed 4/2

6:00 am-7:37 am

Nonstop1h 37m

Newark

Tue 4/8

11:12 am-12:48 pm

Nonstop1h 36m

$163

NorfolkNewark

ORF - EWR

ORFEWR

Norfolk

Thu 2/6

10:57 am-10:00 pm

1 stop11h 03m

Newark

Tue 2/11

6:41 pm-3:32 pm

1 stop20h 51m

$165

NorfolkNew York

ORF - LGA

ORFLGA

Norfolk

Fri 2/28

5:45 am-7:20 am

Nonstop1h 35m

New York LaGuardia

Sun 3/2

10:30 am-11:53 am

Nonstop1h 23m

$179

NorfolkNew York

ORF - JFK

ORFJFK

Norfolk

Thu 2/20

3:27 pm-4:51 pm

Nonstop1h 24m

New York John F Kennedy Intl

Sun 2/23

9:20 pm-10:52 pm

Nonstop1h 32m

$179

NorfolkNew York

ORF - LGA

ORFLGA

Norfolk

Fri 2/28

4:29 pm-10:49 pm

1 stop6h 20m

New York LaGuardia

Mon 3/3

5:59 pm-5:34 pm

1 stop23h 35m

$182

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

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.

Travel insights for flights from Chesapeake to Connecticut

Get recent, data-driven insights about flights from Chesapeake to Connecticut including ideal travel times, pricing trends, and more.

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 January 21, 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 January 21, 2025.
See what other customers who have flown with Delta, American Airlines and Frontier from Chesapeake to Connecticut have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Breeze Airways
8.1
Very good
144 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,201 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,985 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $36 on Breeze Airways. Other airlines that offer cheap prices include Frontier from $55 and Spirit Airlines from $72 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 $39. On average you can expect to pay $141. The most popular route, (Norfolk - Newark), can usually be booked for $140.

  • 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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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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$58Average$126FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$165Average$342FlexibilityNo cancel feeOn-time69%
DeltaCheapest$175Average$247FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$191Average$365FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$211Average$341FlexibilityNo cancel feeOn-time63%
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