$54+ Cheap flights from Chesapeake, VA to Connecticut
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — BDL
Oct 17 — Oct 241
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 September 17, 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 September 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Mon 12/79:22 pm -
Nonstop1h 27m
Tue 12/157:15 am -
Nonstop1h 38m
Deal found 9/15![Breeze Airways logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 12/89:06 pm -
Nonstop1h 27m
Tue 12/157:15 am -
Nonstop1h 38m
Deal found 9/14![Breeze Airways logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 12/109:06 pm -
Nonstop1h 27m
Tue 12/157:15 am -
Nonstop1h 38m
Deal found 9/14![Breeze Airways logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 12/119:22 pm -
Nonstop1h 27m
Tue 12/157:15 am -
Nonstop1h 38m
Deal found 9/14![Breeze Airways logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Mon 12/79:22 pm -
Nonstop1h 27m
Fri 12/187:05 am -
Nonstop1h 38m
Deal found 9/14![Breeze Airways logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 11/129:06 pm -
Nonstop1h 27m
Sun 11/157:15 am -
Nonstop1h 38m
Deal found 9/14![Breeze Airways logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 12/159:06 pm -
Nonstop1h 27m
Fri 12/187:05 am -
Nonstop1h 38m
Deal found 9/14![Breeze Airways logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 11/63:49 pm -
Nonstop1h 27m
Mon 11/95:56 pm -
Nonstop1h 27m
Deal found 9/15![Breeze Airways logo]()
$138
This Breeze Airways deal was found by Cheapflights users on 9/14. 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 9/249:48 am -
Nonstop1h 27m
Mon 10/57:05 am -
Nonstop1h 38m
Deal found 9/14![Breeze Airways logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/149:59 pm -
Nonstop1h 27m
Sat 10/177:00 am -
Nonstop1h 37m
Deal found 9/14![Breeze Airways logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 11/69:22 pm -
Nonstop1h 27m
Sun 11/87:15 am -
Nonstop1h 38m
Deal found 9/16![Breeze Airways logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/299:25 pm -
Nonstop1h 27m
Mon 11/25:56 pm -
Nonstop1h 27m
Deal found 9/16![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 September 17, 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 September 17, 2026.
This Breeze Airways deal was found by Cheapflights users on 9/13. 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 10/79:59 pm -
Nonstop1h 27m
Sat 10/1012:17 pm -
1 stop5h 46m
Deal found 9/13![Breeze Airways logo]()
$204
This Delta deal was found by Cheapflights users on 9/15. 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 12/71:32 pm -
1 stop7h 03m
Tue 12/159:39 am -
1 stop6h 32m
Deal found 9/15![Delta logo]()
$249
This Southwest deal was found by Cheapflights users on 9/16. 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 11/65:55 pm -
1 stop5h 55m
Mon 11/912:45 pm -
2 stops9h 25m
Deal found 9/16![Southwest logo]()
$285
This United Airlines deal was found by Cheapflights users on 9/14. 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 11/46:24 pm -
Nonstop1h 41m
Thu 11/126:00 am -
1 stop3h 43m
Deal found 9/14![United Airlines logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/217:41 pm -
1 stop23h 33m
Mon 10/266:24 pm -
2 stops24h 20m
Deal found 9/16![Multiple Airlines logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/109:59 pm -
Nonstop1h 27m
Sat 10/1712:17 pm -
1 stop5h 46m
Deal found 9/12![Breeze Airways logo]()
$253
This Delta deal was found by Cheapflights users on 9/12. 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 12/122:35 pm -
Nonstop1h 30m
Sat 1/911:45 am -
Nonstop1h 33m
Deal found 9/12![Delta logo]()
$293
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Mon 11/236:02 pm -
Nonstop2h 00m
Mon 11/307:59 pm -
1 stop3h 45m
Deal found 9/16![United Airlines logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 10/159:50 pm -
1 stop25h 59m
Mon 10/195:56 pm -
Nonstop1h 27m
Deal found 9/17![Breeze Airways logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 11/73:50 pm -
2 stops44h 00m
Fri 11/1312:30 pm -
1 stop11h 48m
Deal found 9/15![Multiple Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 9/14. 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 11/175:19 pm -
1 stop6h 40m
Sun 11/226:00 am -
1 stop6h 21m
Deal found 9/14![Delta logo]()
$305
This United Airlines deal was found by Cheapflights users on 9/12. 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.
Sat 10/105:49 pm -
Nonstop1h 46m
Sat 10/179:17 pm -
Nonstop1h 36m
Deal found 9/12![United Airlines logo]()
$307
This CheapOair deal was found by Cheapflights users on 9/12. 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 10/229:25 pm -
Nonstop1h 27m
Sun 10/252:40 pm -
Nonstop1h 37m
Deal found 9/12![Breeze Airways logo]()
$285
This Southwest deal was found by Cheapflights users on 9/15. 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 12/221:25 pm -
1 stop6h 15m
Tue 12/298:30 am -
1 stop4h 15m
Deal found 9/15![Southwest logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 11/123:49 pm -
1 stop20h 01m
Sun 11/157:54 pm -
1 stop18h 55m
Deal found 9/13![Multiple Airlines logo]()
$341
This Delta deal was found by Cheapflights users on 9/15. 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 12/28:29 am -
Nonstop1h 30m
Sat 12/57:59 pm -
Nonstop1h 38m
Deal found 9/15![Delta logo]()
$313
This Southwest deal was found by Cheapflights users on 9/12. 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.
Sat 10/1010:45 am -
2 stops11h 20m
Sat 10/175:40 am -
2 stops10h 40m
Deal found 9/12![Southwest logo]()
$369
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Sat 10/246:00 am -
Nonstop1h 34m
Sun 10/259:03 pm -
Nonstop1h 39m
Deal found 9/15![United Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 9/14. 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 10/1312:00 pm -
Nonstop1h 29m
Sat 10/179:50 am -
Nonstop1h 32m
Deal found 9/14![Delta logo]()
$313
This Breeze Airways deal was found by Cheapflights users on 9/14. 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 10/19:25 pm -
Nonstop1h 27m
Wed 10/712:17 pm -
1 stop5h 46m
Deal found 9/14![Breeze Airways logo]()
$328
This Delta deal was found by Cheapflights users on 9/14. 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 10/1312:00 pm -
Nonstop1h 29m
Tue 10/209:47 am -
Nonstop1h 33m
Deal found 9/14![Delta logo]()
$313
This Southwest deal was found by Cheapflights users on 9/14. 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.
Mon 10/126:05 pm -
1 stop5h 50m
Thu 10/158:50 am -
2 stops13h 00m
Deal found 9/14![Southwest logo]()
$388
This United Airlines deal was found by Cheapflights users on 9/15. 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 10/166:15 am -
1 stop3h 42m
Sun 10/187:59 pm -
1 stop3h 45m
Deal found 9/15![United Airlines logo]()
$354
This Breeze Airways deal was found by Cheapflights users on 9/12. 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 9/12![Breeze Airways logo]()
$333
This Delta deal was found by Cheapflights users on 9/13. 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 10/62:25 pm -
Nonstop1h 33m
Wed 10/147:45 am -
Nonstop1h 28m
Deal found 9/13![Delta logo]()
$328
This United Airlines deal was found by Cheapflights users on 9/12. 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 11/86:00 am -
1 stop3h 43m
Deal found 9/12![United Airlines logo]()
$369
This CheapOair deal was found by Cheapflights users on 9/12. 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 10/19:06 pm -
Nonstop1h 27m
Sat 10/107:36 pm -
1 stop16h 46m
Deal found 9/12![Multiple Airlines logo]()
$456
This Southwest deal was found by Cheapflights users on 9/14. 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.
Wed 2/177:45 am -
1 stop7h 45m
Sun 2/2112:30 pm -
2 stops10h 55m
Deal found 9/14![Southwest logo]()
$416
This Delta deal was found by Cheapflights users on 9/12. 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 11/255:10 pm -
Nonstop1h 43m
Sat 11/282:58 pm -
Nonstop1h 31m
Deal found 9/12![Delta logo]()
$333
This United Airlines deal was found by Cheapflights users on 9/15. 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 11/126:00 am -
Nonstop1h 44m
Mon 11/167:59 pm -
1 stop3h 45m
Deal found 9/15![United Airlines logo]()
$369
Last-minute flights from Chesapeake to ConnecticutDiscover last-minute flight deals from Chesapeake to Connecticut. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chesapeake to Connecticut. Data last updated September 17, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 9/14. 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.
Wed 9/239:59 pm -
Nonstop1h 27m
Wed 9/307:00 am -
Nonstop1h 37m
Deal found 9/14![Breeze Airways logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 9/239:59 pm -
Nonstop1h 27m
Sat 10/37:00 am -
Nonstop1h 37m
Deal found 9/14![Breeze Airways logo]()
$172
This Breeze Airways deal was found by Cheapflights users on 9/14. 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 9/249:48 am -
Nonstop1h 27m
Mon 10/57:05 am -
Nonstop1h 38m
Deal found 9/14![Breeze Airways logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 9/249:48 am -
Nonstop1h 27m
Mon 9/287:05 am -
Nonstop1h 38m
Deal found 9/12![Breeze Airways logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 9/309:59 pm -
Nonstop1h 27m
Fri 10/25:56 pm -
Nonstop1h 27m
Deal found 9/16![Breeze Airways logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 10/109:59 pm -
Nonstop1h 27m
Sat 10/177:00 am -
Nonstop1h 37m
Deal found 9/12![Breeze Airways logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/149:59 pm -
Nonstop1h 27m
Sat 10/177:00 am -
Nonstop1h 37m
Deal found 9/14![Breeze Airways logo]()
$142
This Breeze Airways deal was found by Cheapflights users on 9/14. 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 10/229:06 pm -
Nonstop1h 27m
Sun 10/257:15 am -
Nonstop1h 38m
Deal found 9/14![Breeze Airways logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/229:06 pm -
Nonstop1h 27m
Fri 10/237:05 am -
Nonstop1h 38m
Deal found 9/13![Breeze Airways logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/299:25 pm -
Nonstop1h 27m
Mon 11/25:56 pm -
Nonstop1h 27m
Deal found 9/16![Breeze Airways logo]()
$143
This CheapOair deal was found by Cheapflights users on 9/12. 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 10/299:25 pm -
Nonstop1h 27m
Sun 11/12:40 pm -
Nonstop1h 37m
Deal found 9/12![Breeze Airways logo]()
$173
This CheapOair deal was found by Cheapflights users on 9/17. 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 10/303:49 pm -
Nonstop1h 27m
Sun 11/12:40 pm -
Nonstop1h 37m
Deal found 9/17![Breeze Airways logo]()
$167
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 September 17, 2026.
Search for one-way flight options from Chesapeake to Connecticut. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/279:06 pm -
Nonstop1h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Breeze Airways logo]()
$54
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 12/109:25 pm -
Nonstop1h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Breeze Airways logo]()
$69
This CheapOair deal was found by Cheapflights users on 9/16. 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.
Wed 10/219:59 pm -
Nonstop1h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Breeze Airways logo]()
$71
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/249:59 pm -
Nonstop1h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Breeze Airways logo]()
$73
This CheapOair deal was found by Cheapflights users on 9/16. 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.
Wed 9/309:59 pm -
Nonstop1h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Breeze Airways logo]()
$74
This CheapOair deal was found by Cheapflights users on 9/16. 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Breeze Airways logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Mon 10/269:22 pm -
Nonstop1h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Breeze Airways logo]()
$78
This CheapOair deal was found by Cheapflights users on 9/16. 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.
Sun 1/177:41 pm -
Nonstop1h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Breeze Airways logo]()
$81
This CheapOair deal was found by Cheapflights users on 9/16. 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 10/233:49 pm -
Nonstop1h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Breeze Airways logo]()
$86
This CheapOair deal was found by Cheapflights users on 9/16. 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.
Sun 2/77:41 pm -
Nonstop1h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Breeze Airways logo]()
$87
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 12/69:06 pm -
Nonstop1h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Breeze Airways logo]()
$88
This Priceline deal was found by Cheapflights users on 9/16. 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.
Tue 11/31:44 pm -
1 stop7h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$89
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 September 17, 2026.
Round-trip from | $87 (Kiwi.com) |
|---|---|
One-way from | $54 (Kiwi.com) |
Popular in | February |
Cheapest in | September |
Average price | $172 |
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 7,457,451 searches. Data last updated September 17, 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
NorfolkProvidence
ORF Norfolk - PVD Providence-TFGreen
ORFPVD
Norfolk
Thu 1/21
7:41 pm-9:08 pm
Nonstop1h 27m
Providence-TFGreen
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$71
NorfolkProvidence
ORF Norfolk - PVD Providence-TFGreen
ORFPVD
Norfolk
Wed 11/4
9:59 pm-11:26 pm
Nonstop1h 27m
Providence-TFGreen
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$71
NorfolkProvidence
ORF Norfolk - PVD Providence-TFGreen
ORFPVD
Norfolk
Wed 12/9
9:59 pm-11:26 pm
Nonstop1h 27m
Providence-TFGreen
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$71
NorfolkProvidence
ORF Norfolk - PVD Providence-TFGreen
ORFPVD
Norfolk
Thu 1/28
7:41 pm-9:08 pm
Nonstop1h 27m
Providence-TFGreen
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$71
NorfolkProvidence
ORF Norfolk - PVD Providence-TFGreen
ORFPVD
Norfolk
Sat 11/14
9:59 pm-11:26 pm
Nonstop1h 27m
Providence-TFGreen
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$71
NorfolkProvidence
ORF Norfolk - PVD Providence-TFGreen
ORFPVD
Norfolk
Sun 1/31
7:41 pm-9:08 pm
Nonstop1h 27m
Providence-TFGreen
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$76
NorfolkProvidence
ORF Norfolk - PVD Providence-TFGreen
ORFPVD
Norfolk
Sun 1/24
7:41 pm-9:08 pm
Nonstop1h 27m
Providence-TFGreen
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$81
NorfolkProvidence
ORF Norfolk - PVD Providence-TFGreen
ORFPVD
Norfolk
Sun 10/18
9:25 pm-10:52 pm
Nonstop1h 27m
Providence-TFGreen
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$92
NorfolkProvidence
ORF Norfolk - PVD Providence-TFGreen
ORFPVD
Norfolk
Tue 12/22
9:06 pm-10:33 pm
Nonstop1h 27m
Providence-TFGreen
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$102
NorfolkProvidence
ORF Norfolk - PVD Providence-TFGreen
ORFPVD
Norfolk
Fri 1/1
3:49 pm-5:16 pm
Nonstop1h 27m
Providence-TFGreen
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$113
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-PVD
ORF-BDL
ORF-EWR
ORF-JFK
ORF-HVN
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-PVD
ORF-BDL
ORF-EWR
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 September 17, 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 53% 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 $116 and $389 in January.The cheapest round-trip price found within the last 5 days was $87 on Breeze Airways (Jan 21-Jan 25).
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 September 17, 2026.
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.
Comfort
8.2
Boarding
8.4
Crew
8.8
Food
6.8
Overall
8.2
Entertainment
6.8
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Comfort
8.2
Boarding
8.4
Crew
8.8
Food
6.8
Overall
8.2
Entertainment
6.8
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Comfort
8.2
Boarding
8.4
Crew
8.8
Food
6.8
Overall
8.2
Entertainment
6.8
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Comfort
8.2
Boarding
8.4
Crew
8.8
Food
6.8
Overall
8.2
Entertainment
6.8
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Comfort
8.2
Boarding
8.4
Crew
8.8
Food
6.8
Overall
8.2
Entertainment
6.8
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 September 17, 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 7,457,451 searches. Data last updated September 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$78 | Average$151 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$188 | Average$319 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$198 | Average$501 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$275 | Average$461 | FlexibilityNo cancel fee | On-time69% |