$51+ 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 9/3. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — BDL
Sep 5 — Sep 121
Round-trip
1 adult, Economy
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Cheapest flights from Chesapeake to ConnecticutExplore 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 August 6, 2026.
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 August 6, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
Sat 9/510:30 pm -
Nonstop1h 29m
Sun 9/68:00 am -
Nonstop1h 31m
Deal found 8/5![Breeze Airways logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 8/2710:11 am -
Nonstop1h 29m
Sun 8/308:00 am -
Nonstop1h 31m
Deal found 8/3![Breeze Airways logo]()
$102
This Breeze Airways deal was found by Cheapflights users on 8/2. 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.
Thu 8/2710:11 am -
Nonstop1h 29m
Sat 8/297:35 am -
Nonstop1h 31m
Deal found 8/2![Breeze Airways logo]()
$103
This CheapOair deal was found by Cheapflights users on 8/4. 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 8/2712:11 pm -
Nonstop1h 23m
Sun 8/302:34 pm -
Nonstop1h 24m
Deal found 8/4![Breeze Airways logo]()
$107
This Breeze Airways deal was found by Cheapflights users on 8/4. 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.
Thu 8/2012:11 pm -
Nonstop1h 23m
Sun 8/232:34 pm -
Nonstop1h 24m
Deal found 8/4![Breeze Airways logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
Fri 9/119:22 pm -
Nonstop1h 27m
Sun 9/137:30 am -
Nonstop1h 38m
Deal found 8/5![Breeze Airways logo]()
$132
This Breeze Airways deal was found by Cheapflights users on 8/3. 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.
Tue 11/179:06 pm -
Nonstop1h 27m
Sun 11/227:15 am -
Nonstop1h 38m
Deal found 8/3![Breeze Airways logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
Tue 9/82:16 pm -
Nonstop1h 28m
Sat 9/127:00 am -
Nonstop1h 37m
Deal found 8/5![Breeze Airways logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Tue 9/12:16 pm -
Nonstop1h 28m
Sun 9/67:30 am -
Nonstop1h 33m
Deal found 8/3![Breeze Airways logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 8/2. 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.
Sat 9/129:59 pm -
Nonstop1h 27m
Sat 9/197:00 am -
Nonstop1h 37m
Deal found 8/2![Breeze Airways logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 8/6. 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 11/59:06 pm -
Nonstop1h 27m
Mon 11/97:05 am -
Nonstop1h 38m
Deal found 8/6![Breeze Airways logo]()
$142
This Breeze Airways deal was found by Cheapflights users on 8/2. 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.
Sat 8/2210:30 pm -
Nonstop1h 29m
Sat 8/297:35 am -
Nonstop1h 31m
Deal found 8/2![Breeze Airways logo]()
$143
Best flights from Chesapeake to ConnecticutDiscover carefully curated flight deals from Chesapeake to Connecticut that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 6, 2026.
Discover carefully curated flight deals from Chesapeake to Connecticut that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 6, 2026.
This CheapOair deal was found by Cheapflights users on 8/5. 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 8/2712:11 pm -
Nonstop1h 23m
Sun 8/302:34 pm -
Nonstop1h 24m
Deal found 8/5![Breeze Airways logo]()
$107
This Delta deal was found by Cheapflights users on 8/2. 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 9/158:00 am -
1 stop8h 07m
Sat 9/195:13 pm -
1 stop6h 20m
Deal found 8/2![Delta logo]()
$189
This Breeze Airways deal was found by Cheapflights users on 8/4. 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.
Thu 8/2012:11 pm -
Nonstop1h 23m
Sun 8/232:34 pm -
Nonstop1h 24m
Deal found 8/4![Breeze Airways logo]()
$108
This United Airlines deal was found by Cheapflights users on 8/4. 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.
Fri 11/66:00 am -
Nonstop1h 44m
Sun 11/88:55 pm -
Nonstop1h 39m
Deal found 8/4![United Airlines logo]()
$249
This Southwest deal was found by Cheapflights users on 8/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:15 am -
1 stop3h 25m
Wed 9/28:05 am -
2 stops9h 15m
Deal found 8/5![Southwest logo]()
$274
This JetBlue deal was found by Cheapflights users on 8/5. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:25 am -
1 stop6h 42m
Mon 9/281:00 pm -
1 stop5h 23m
Deal found 8/5![JetBlue logo]()
$291
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 8/1612:11 pm -
Nonstop1h 23m
Tue 8/181:11 pm -
2 stops51h 00m
Deal found 8/5![Multiple Airlines logo]()
$296
This Breeze Airways deal was found by Cheapflights users on 8/5. 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.
Wed 9/239:59 pm -
Nonstop1h 27m
Fri 9/255:56 pm -
Nonstop1h 27m
Deal found 8/5![Breeze Airways logo]()
$153
This Delta deal was found by Cheapflights users on 8/1. 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.
Mon 9/215:02 pm -
1 stop6h 57m
Wed 9/235:55 pm -
1 stop6h 40m
Deal found 8/1![Delta logo]()
$189
This Breeze Airways deal was found by Cheapflights users on 8/1. 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.
Thu 9/179:25 pm -
Nonstop1h 27m
Sun 9/202:40 pm -
Nonstop1h 37m
Deal found 8/1![Breeze Airways logo]()
$158
This Breeze Airways deal was found by Cheapflights users on 8/4. 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.
Sat 8/2210:30 pm -
Nonstop1h 29m
Sat 8/297:35 am -
Nonstop1h 31m
Deal found 8/4![Breeze Airways logo]()
$158
This Delta deal was found by Cheapflights users on 8/2. 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 11/175:30 am -
1 stop6h 50m
Sun 11/221:25 pm -
1 stop6h 57m
Deal found 8/2![Delta logo]()
$199
This Breeze Airways deal was found by Cheapflights users on 8/3. 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.
Fri 11/69:22 pm -
Nonstop1h 27m
Tue 11/107:15 am -
Nonstop1h 38m
Deal found 8/3![Breeze Airways logo]()
$158
This Delta deal was found by Cheapflights users on 8/3. 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 10/75:30 am -
1 stop4h 49m
Sat 10/105:14 pm -
1 stop6h 18m
Deal found 8/3![Delta logo]()
$214
This United Airlines deal was found by Cheapflights users on 8/4. 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.
Fri 1/17:50 pm -
1 stop4h 11m
Fri 1/86:00 am -
1 stop3h 35m
Deal found 8/4![United Airlines logo]()
$269
This Southwest deal was found by Cheapflights users on 8/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:45 pm -
1 stop5h 30m
Wed 9/3012:55 pm -
2 stops8h 00m
Deal found 8/4![Southwest logo]()
$283
This JetBlue deal was found by Cheapflights users on 8/4. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:25 am -
1 stop6h 42m
Mon 9/141:00 pm -
1 stop5h 23m
Deal found 8/4![JetBlue logo]()
$291
This JetBlue deal was found by Cheapflights users on 8/4. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:25 am -
1 stop6h 42m
Fri 9/253:45 pm -
1 stop6h 56m
Deal found 8/4![JetBlue logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 8/1. 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.
Fri 10/2312:57 pm -
1 stop7h 58m
Mon 10/266:25 am -
2 stops17h 53m
Deal found 8/1![Multiple Airlines logo]()
$346
This United Airlines deal was found by Cheapflights users on 8/4. 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.
Thu 11/510:47 am -
Nonstop1h 41m
Sun 11/88:55 pm -
Nonstop1h 39m
Deal found 8/4![United Airlines logo]()
$319
This Breeze Airways deal was found by Cheapflights users on 8/1. 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.
Sat 10/109:59 pm -
Nonstop1h 27m
Mon 10/125:56 pm -
Nonstop1h 27m
Deal found 8/1![Breeze Airways logo]()
$218
This Delta deal was found by Cheapflights users on 8/1. 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 10/712:08 pm -
Nonstop1h 31m
Wed 10/219:20 pm -
Nonstop1h 43m
Deal found 8/1![Delta logo]()
$273
This United Airlines deal was found by Cheapflights users on 8/5. 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 9/16:10 pm -
Nonstop1h 50m
Tue 9/89:22 pm -
Nonstop1h 32m
Deal found 8/5![United Airlines logo]()
$319
This Breeze Airways deal was found by Cheapflights users on 8/5. 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.
Fri 8/218:06 pm -
Nonstop1h 29m
Sun 8/238:00 am -
Nonstop1h 31m
Deal found 8/5![Breeze Airways logo]()
$218
This Delta deal was found by Cheapflights users on 8/4. 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.
Sat 9/195:35 pm -
Nonstop1h 48m
Sat 9/269:00 pm -
Nonstop1h 41m
Deal found 8/4![Delta logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 8/1612:11 pm -
Nonstop1h 23m
Mon 8/176:55 pm -
3 stops17h 30m
Deal found 8/5![Multiple Airlines logo]()
$375
This United Airlines deal was found by Cheapflights users on 8/3. 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.
Thu 9/36:15 am -
1 stop5h 32m
Sun 9/69:25 pm -
Nonstop1h 37m
Deal found 8/3![United Airlines logo]()
$329
This Breeze Airways deal was found by Cheapflights users on 8/5. 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.
Fri 8/2110:08 pm -
Nonstop1h 28m
Sun 8/237:30 am -
Nonstop1h 33m
Deal found 8/5![Breeze Airways logo]()
$228
This Delta deal was found by Cheapflights users on 8/6. 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.
Sat 9/122:00 pm -
Nonstop1h 32m
Sun 9/207:50 am -
Nonstop1h 28m
Deal found 8/6![Delta logo]()
$283
This United Airlines deal was found by Cheapflights users on 8/3. 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 8/256:00 am -
Nonstop1h 35m
Mon 8/318:15 am -
1 stop6h 00m
Deal found 8/3![United Airlines logo]()
$329
Last-minute flights from Chesapeake to ConnecticutDiscover last-minute flight deals from Chesapeake to Connecticut. Data last updated August 6, 2026 and is based on user searches.
Discover last-minute flight deals from Chesapeake to Connecticut. Data last updated August 6, 2026 and is based on user searches.
This Breeze Airways deal was found by Cheapflights users on 8/4. 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.
Thu 8/2012:11 pm -
Nonstop1h 23m
Sun 8/232:34 pm -
Nonstop1h 24m
Deal found 8/4![Breeze Airways logo]()
$108
This Breeze Airways deal was found by Cheapflights users on 8/2. 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.
Sat 8/2210:30 pm -
Nonstop1h 29m
Sat 8/297:35 am -
Nonstop1h 31m
Deal found 8/2![Breeze Airways logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 8/3. 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 8/2710:11 am -
Nonstop1h 29m
Sun 8/308:00 am -
Nonstop1h 31m
Deal found 8/3![Breeze Airways logo]()
$102
This Breeze Airways deal was found by Cheapflights users on 8/2. 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.
Thu 8/2710:11 am -
Nonstop1h 29m
Sat 8/297:35 am -
Nonstop1h 31m
Deal found 8/2![Breeze Airways logo]()
$103
This CheapOair deal was found by Cheapflights users on 8/4. 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 8/2712:11 pm -
Nonstop1h 23m
Sun 8/302:34 pm -
Nonstop1h 24m
Deal found 8/4![Breeze Airways logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Tue 9/12:16 pm -
Nonstop1h 28m
Sun 9/67:30 am -
Nonstop1h 33m
Deal found 8/3![Breeze Airways logo]()
$138
This CheapOair deal was found by Cheapflights users on 8/5. 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.
Tue 9/12:16 pm -
Nonstop1h 28m
Wed 9/27:35 am -
Nonstop1h 33m
Deal found 8/5![Breeze Airways logo]()
$147
This Breeze Airways deal was found by Cheapflights users on 8/3. 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.
Fri 9/48:06 pm -
Nonstop1h 29m
Sun 9/68:00 am -
Nonstop1h 31m
Deal found 8/3![Breeze Airways logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
Sat 9/510:30 pm -
Nonstop1h 29m
Sun 9/68:00 am -
Nonstop1h 31m
Deal found 8/5![Breeze Airways logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
Tue 9/82:16 pm -
Nonstop1h 28m
Sat 9/127:00 am -
Nonstop1h 37m
Deal found 8/5![Breeze Airways logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
Fri 9/119:22 pm -
Nonstop1h 27m
Sun 9/137:30 am -
Nonstop1h 38m
Deal found 8/5![Breeze Airways logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 8/2. 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.
Sat 9/129:59 pm -
Nonstop1h 27m
Sat 9/197:00 am -
Nonstop1h 37m
Deal found 8/2![Breeze Airways logo]()
$142
One-way flights from Chesapeake to ConnecticutSearch for one-way flight options from Chesapeake to Connecticut. Find affordable one-way fares based on user searches. Data last updated August 6, 2026.
Search for one-way flight options from Chesapeake to Connecticut. Find affordable one-way fares based on user searches. Data last updated August 6, 2026.
This CheapOair deal was found by Cheapflights users on 8/2. 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 9/310:11 am -
Nonstop1h 23m
Deal found 8/2![Breeze Airways logo]()
$51
This Kiwi.com deal was found by Cheapflights users on 8/5. 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 8/1612:11 pm -
Nonstop1h 23m
Deal found 8/5![Breeze Airways logo]()
$63
This Kiwi.com deal was found by Cheapflights users on 8/2. 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.
Fri 8/288:06 pm -
Nonstop1h 29m
Deal found 8/2![Breeze Airways logo]()
$64
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Sat 9/510:31 pm -
Nonstop1h 28m
Deal found 8/3![Breeze Airways logo]()
$69
This CheapOair deal was found by Cheapflights users on 8/1. 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.
Tue 9/82:16 pm -
Nonstop1h 28m
Deal found 8/1![Breeze Airways logo]()
$71
This Kiwi.com deal was found by Cheapflights users on 8/6. 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.
Sat 9/129:59 pm -
Nonstop1h 27m
Deal found 8/6![Breeze Airways logo]()
$73
This Kiwi.com deal was found by Cheapflights users on 8/1. 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.
Wed 8/1910:30 pm -
Nonstop1h 29m
Deal found 8/1![Breeze Airways logo]()
$73
This CheapOair deal was found by Cheapflights users on 8/1. 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 11/133:49 pm -
Nonstop1h 27m
Deal found 8/1![Breeze Airways logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 8/2010:11 am -
Nonstop1h 29m
Deal found 8/1![Breeze Airways logo]()
$79
This CheapOair deal was found by Cheapflights users on 8/2. 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 10/179:59 pm -
Nonstop1h 27m
Deal found 8/2![Breeze Airways logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
Fri 9/410:08 pm -
Nonstop1h 28m
Deal found 8/5![Breeze Airways logo]()
$83
This Super.com deal was found by Cheapflights users on 8/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/221:18 pm -
1 stop8h 06m
Deal found 8/3![Frontier logo]()
$84
Find flight deals from Chesapeake to Connecticut
Keep the following information in mind while searching for Chesapeake to Connecticut flight deals. Data was last updated August 6, 2026.
Round-trip from | $88 (Kiwi.com) |
|---|---|
One-way from | $51 (CheapOair) |
Popular in | February |
Cheapest in | January |
Average price | $193 |
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 August 6, 2026.
Use the filters below to find and compare flights from Chesapeake to Connecticut that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
NorfolkNew Haven
ORF Norfolk - HVN Tweed-New Haven
ORFHVN
Norfolk
Thu 8/27
12:11 pm-1:34 pm
Nonstop1h 23m
Tweed-New Haven
Sun 8/30
2:34 pm-3:58 pm
Nonstop1h 24m
$107
NorfolkNew Haven
ORF Norfolk - HVN Tweed-New Haven
ORFHVN
Norfolk
Thu 8/20
12:11 pm-1:34 pm
Nonstop1h 23m
Tweed-New Haven
Sun 8/23
2:34 pm-3:58 pm
Nonstop1h 24m
$108
NorfolkProvidence
ORF Norfolk - PVD Providence-TFGreen
ORFPVD
Norfolk
Wed 9/23
9:59 pm-11:26 pm
Nonstop1h 27m
Providence-TFGreen
Fri 9/25
5:56 pm-7:23 pm
Nonstop1h 27m
$153
NorfolkProvidence
ORF Norfolk - PVD Providence-TFGreen
ORFPVD
Norfolk
Thu 9/17
9:25 pm-10:52 pm
Nonstop1h 27m
Providence-TFGreen
Sun 9/20
2:40 pm-4:17 pm
Nonstop1h 37m
$158
NorfolkHartford
ORF Norfolk - BDL Hartford Bradley Intl
ORFBDL
Norfolk
Sat 8/22
10:30 pm-11:59 pm
Nonstop1h 29m
Hartford Bradley Intl
Sat 8/29
7:35 am-9:06 am
Nonstop1h 31m
$158
NorfolkHartford
ORF Norfolk - BDL Hartford Bradley Intl
ORFBDL
Norfolk
Fri 11/6
9:22 pm-10:49 pm
Nonstop1h 27m
Hartford Bradley Intl
Tue 11/10
7:15 am-8:53 am
Nonstop1h 38m
$158
NorfolkHartford
ORF Norfolk - BDL Hartford Bradley Intl
ORFBDL
Norfolk
Tue 9/15
8:00 am-4:07 pm
1 stop8h 07m
Hartford Bradley Intl
Sat 9/19
5:13 pm-11:33 pm
1 stop6h 20m
$189
NorfolkHartford
ORF Norfolk - BDL Hartford Bradley Intl
ORFBDL
Norfolk
Mon 9/21
5:02 pm-11:59 pm
1 stop6h 57m
Hartford Bradley Intl
Wed 9/23
5:55 pm-12:35 am
1 stop6h 40m
$189
NorfolkProvidence
ORF Norfolk - PVD Providence-TFGreen
ORFPVD
Norfolk
Tue 11/17
5:30 am-12:20 pm
1 stop6h 50m
Providence-TFGreen
Sun 11/22
1:25 pm-8:22 pm
1 stop6h 57m
$199
NorfolkHartford
ORF Norfolk - BDL Hartford Bradley Intl
ORFBDL
Norfolk
Wed 10/7
5:30 am-10:19 am
1 stop4h 49m
Hartford Bradley Intl
Sat 10/10
5:14 pm-11:32 pm
1 stop6h 18m
$214
Showing 1-10 of 60 resultsSorted by cheapest first
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.
ORF-BDL
ORF-HVN
ORF-PVD
ORF-JFK
ORF-LGA
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
C6E-USCT
ORF-BDL
ORF-HVN
ORF-PVD
ORF-JFK
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 August 6, 2026.
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 49% on airfare.
How much does it cost to fly round-trip from Chesapeake to Connecticut?
Airfare is below average for this route at the moment.
Chesapeake to Connecticut flights typically cost between $173 and $222 in September.The cheapest round-trip price found within the last 5 days was $88 on Breeze Airways (Sep 5-Sep 6).
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 August 6, 2026.
Get a feel of what it's like to fly with Breeze Airways,Southwest, andAmerican 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.
Entertainment
6.7
Food
6.7
Comfort
8.2
Crew
8.7
Overall
8.2
Boarding
8.3
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Entertainment
6.7
Food
6.7
Comfort
8.2
Crew
8.7
Overall
8.2
Boarding
8.3
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Entertainment
6.7
Food
6.7
Comfort
8.2
Crew
8.7
Overall
8.2
Boarding
8.3
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Entertainment
6.7
Food
6.7
Comfort
8.2
Crew
8.7
Overall
8.2
Boarding
8.3
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
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.
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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.
Complete your trip
Complete your trip to Connecticut by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chesapeake to Connecticut by cabin class
Find flights from Chesapeake to Connecticut, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chesapeake and Connecticut flights
Browse other Chesapeake and Connecticut flight options. Last updated on August 6, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Connecticut
Find the right flight back to Chesapeake after your stay in Connecticut
Top 4 airlines flying from Chesapeake to Connecticut
Discover the top 4 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 August 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$78 | Average$151 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$156 | Average$346 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$196 | Average$470 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$290 | Average$437 | FlexibilityNo cancel fee | On-time69% |