HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Connecticut

$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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — BDL
ago. 5 — ago. 121
mar. 8/5
mar. 8/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chesapeake to Connecticut with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 julio 31, 2025.

Round-trip from

$78
(Breeze Airways)

One-way from

$41
(CheapOair)
From Chesapeake to Connecticut
Search Deals
One-way flight from Chesapeake to Connecticut
Search Deals

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 julio 31, 2025.

This Breeze Airways deal was found by Cheapflights users on 7/30. 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.
dom. 9/149:47 pmORF - PVD
Nonstop1h 26mBreeze Airways
lun. 9/227:00 amPVD - ORF
Nonstop1h 36mBreeze Airways
Deal found 7/30$78
This Breeze Airways deal was found by Cheapflights users on 7/30. 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.
jue. 9/1810:32 amORF - BDL
Nonstop1h 27mBreeze Airways
dom. 9/218:15 amBDL - ORF
Nonstop1h 37mBreeze Airways
Deal found 7/30$103
This Breeze Airways deal was found by Cheapflights users on 7/28. 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.
vie. 10/101:56 pmORF - HVN
Nonstop1h 30mBreeze Airways
lun. 10/134:06 pmHVN - ORF
Nonstop1h 30mBreeze Airways
Deal found 7/28$113
This Booking.com deal was found by Cheapflights users on 7/30. 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.
mié. 8/135:30 amORF - EWR
1 stop12h 29mSpirit Airlines
sáb. 8/3010:31 amEWR - ORF
1 stop12h 03mSpirit Airlines
Deal found 7/30$178
This Delta deal was found by Cheapflights users on 7/30. 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.
vie. 8/226:06 amORF - LGA
Nonstop1h 24mDelta
lun. 8/254:25 pmLGA - ORF
Nonstop1h 42mDelta
Deal found 7/30$179
This United Airlines deal was found by Cheapflights users on 7/29. 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.
jue. 8/286:00 amORF - EWR
Nonstop1h 20mUnited Airlines
dom. 8/3110:00 pmEWR - ORF
Nonstop1h 31mUnited Airlines
Deal found 7/29$179
This Delta deal was found by Cheapflights users on 7/31. 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.
jue. 8/215:31 pmORF - JFK
Nonstop1h 39mDelta
dom. 8/249:20 pmJFK - ORF
Nonstop1h 56mDelta
Deal found 7/31$179
This Booking.com deal was found by Cheapflights users on 7/30. 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.
vie. 9/52:05 pmORF - LGA
1 stop8h 33mSpirit Airlines
sáb. 9/610:59 amLGA - ORF
1 stop11h 49mSpirit Airlines
Deal found 7/30$180
This American Airlines deal was found by Cheapflights users on 7/31. 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.
vie. 9/126:00 amORF - JFK
Nonstop1h 24mAmerican Airlines
sáb. 9/1310:50 amJFK - ORF
Nonstop1h 24mAmerican Airlines
Deal found 7/31$181
This American Airlines deal was found by Cheapflights users on 7/31. 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.
vie. 8/225:51 pmORF - LGA
Nonstop1h 38mAmerican Airlines
sáb. 8/302:44 pmLGA - ORF
Nonstop1h 29mAmerican Airlines
Deal found 7/31$183
This Frontier deal was found by Cheapflights users on 7/30. 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.
dom. 8/1012:53 pmORF - LGA
1 stop8h 06mFrontier
mié. 8/1310:00 pmLGA - ORF
1 stop13h 51mFrontier
Deal found 7/30$188
This Frontier deal was found by Cheapflights users on 7/30. 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.
sáb. 10/113:27 pmORF - JFK
1 stop9h 13mFrontier
lun. 10/136:15 amJFK - ORF
1 stop8h 12mFrontier
Deal found 7/30$188

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 julio 31, 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

dom. 9/14

9:47 pm-11:13 pm

Nonstop1h 26m

Providence-TFGreen

lun. 9/22

7:00 am-8:36 am

Nonstop1h 36m

$78

NorfolkHartford

ORF - BDL

ORFBDL

Norfolk

jue. 9/18

10:32 am-11:59 am

Nonstop1h 27m

Hartford Bradley Intl

dom. 9/21

8:15 am-9:52 am

Nonstop1h 37m

$103

NorfolkNew Haven

ORF - HVN

ORFHVN

Norfolk

vie. 10/10

1:56 pm-3:26 pm

Nonstop1h 30m

Tweed-New Haven

lun. 10/13

4:06 pm-5:36 pm

Nonstop1h 30m

$113

NorfolkNewark

ORF - EWR

ORFEWR

Norfolk

mié. 8/13

5:30 am-5:59 pm

1 stop12h 29m

Newark

sáb. 8/30

10:31 am-10:34 pm

1 stop12h 03m

$178

NorfolkNew York

ORF - LGA

ORFLGA

Norfolk

vie. 8/22

6:06 am-7:30 am

Nonstop1h 24m

New York LaGuardia

lun. 8/25

4:25 pm-6:07 pm

Nonstop1h 42m

$179

NorfolkNewark

ORF - EWR

ORFEWR

Norfolk

jue. 8/28

6:00 am-7:20 am

Nonstop1h 20m

Newark

dom. 8/31

10:00 pm-11:31 pm

Nonstop1h 31m

$179

NorfolkNew York

ORF - JFK

ORFJFK

Norfolk

jue. 8/21

5:31 pm-7:10 pm

Nonstop1h 39m

New York John F Kennedy Intl

dom. 8/24

9:20 pm-11:16 pm

Nonstop1h 56m

$179

NorfolkNew York

ORF - LGA

ORFLGA

Norfolk

vie. 9/5

2:05 pm-10:38 pm

1 stop8h 33m

New York LaGuardia

sáb. 9/6

10:59 am-10:48 pm

1 stop11h 49m

$180

NorfolkNew York

ORF - JFK

ORFJFK

Norfolk

vie. 9/12

6:00 am-7:24 am

Nonstop1h 24m

New York John F Kennedy Intl

sáb. 9/13

10:50 am-12:14 pm

Nonstop1h 24m

$181

NorfolkNew York

ORF - LGA

ORFLGA

Norfolk

vie. 8/22

5:51 pm-7:29 pm

Nonstop1h 38m

New York LaGuardia

sáb. 8/30

2:44 pm-4:13 pm

Nonstop1h 29m

$183

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 47 results
1
2
3
...
5

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 julio 31, 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 julio 31, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and Breeze Airways 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
4,246 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Breeze Airways
8.0
Very good
191 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 Spirit Airlines from $81 and Frontier from $90 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 $69. On average you can expect to pay $121. The most popular route, (Norfolk - New York LaGuardia), can usually be booked for $167.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chesapeake to Connecticut

See prices for flight routes from nearby airports that may be better suited for you.
Dulles Intl to Miami flights
Dulles Intl to Dallas/Fort Worth flights
Reagan-National to O'Hare Intl flights
Dulles Intl to Las Vegas flights
Reagan-National to Seattle flights
Dulles Intl to O'Hare Intl flights
Reagan-National to Los Angeles flights
Reagan-National to Las Vegas flights
Reagan-National to Dallas/Fort Worth flights
Reagan-National to Boston flights
Dulles Intl to Atlanta flights
Dulles Intl to Los Angeles flights
Reagan-National to Miami flights
Dulles Intl to Boston flights
Dulles Intl to Hobby flights
Reagan-National to San Francisco flights
Dulles Intl to Orlando flights
Dulles Intl to Seattle flights
Dulles Intl to San Francisco flights
Dulles Intl to Fort Lauderdale flights
Raleigh to Las Vegas flights
Reagan-National to Orlando flights
Dulles Intl to Midway flights
Raleigh to O'Hare Intl flights
Reagan-National to Atlanta flights
Raleigh to LaGuardia flights
Dulles Intl to Minneapolis flights
Raleigh to John F Kennedy Intl flights
Reagan-National to Fort Lauderdale flights
Reagan-National to Minneapolis flights
Dulles Intl to George Bush Intcntl flights
Dulles Intl to Tampa flights
Reagan-National to Denver flights
Raleigh to Newark flights
Dulles Intl to Denver flights
Raleigh to Denver flights
Reagan-National to Hobby flights
Dulles Intl to New Orleans flights
Raleigh to Orlando flights
Raleigh to Miami flights
Reagan-National to Nashville flights
Dulles Intl to Ontario flights
Dulles Intl to Sky Harbor Intl flights
Dulles Intl to Cleveland flights
Reagan-National to Tampa flights
Dulles Intl to Honolulu flights
Reagan-National to Sky Harbor Intl flights
Reagan-National to George Bush Intcntl flights
Reagan-National to Cleveland flights
Raleigh to Boston flights

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 julio 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$55Average$105FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$101Average$276FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$176Average$339FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$186Average$366FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$211Average$331FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.