$43+ 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 8/28. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — BDL
May 30 — Jun 61
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 April 30, 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 April 30, 2026.
This Breeze Airways deal was found by Cheapflights users on 4/25. 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 5/1412:16 pm
ORF
- HVN
Nonstop1h 23m
Breeze Airways
Sun 5/242:39 pm
HVN
- ORF
Nonstop1h 24m
Breeze Airways
Deal found 4/25![Breeze Airways logo]()
$103
This Booking.com deal was found by Cheapflights users on 4/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/810:08 pm
ORF
- PVD
Nonstop1h 28m
Breeze Airways
Wed 6/107:35 am
PVD
- ORF
Nonstop1h 33m
Breeze Airways
Deal found 4/29![Breeze Airways logo]()
$107
This Breeze Airways deal was found by Cheapflights users on 4/28. 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.
Wed 5/1310:30 pm
ORF
- BDL
Nonstop1h 29m
Breeze Airways
Thu 5/147:15 am
BDL
- ORF
Nonstop1h 31m
Breeze Airways
Deal found 4/28![Breeze Airways logo]()
$108
This Super.com deal was found by Cheapflights users on 4/27. 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.
Sun 5/1012:16 pm
ORF
- HVN
Nonstop1h 23m
Breeze Airways
Sun 5/172:39 pm
HVN
- ORF
Nonstop1h 24m
Breeze Airways
Deal found 4/27![Breeze Airways logo]()
$112
This CheapOair deal was found by Cheapflights users on 4/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/110:08 pm
ORF
- PVD
Nonstop1h 28m
Breeze Airways
Tue 6/24:43 pm
PVD
- ORF
Nonstop1h 33m
Breeze Airways
Deal found 4/28![Breeze Airways logo]()
$112
This Breeze Airways deal was found by Cheapflights users on 4/28. 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.
Thu 5/2812:16 pm
ORF
- HVN
Nonstop1h 23m
Breeze Airways
Sun 5/312:39 pm
HVN
- ORF
Nonstop1h 24m
Breeze Airways
Deal found 4/28![Breeze Airways logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:16 pm
ORF
- HVN
Nonstop1h 23m
Breeze Airways
Thu 6/42:34 pm
HVN
- ORF
Nonstop1h 24m
Breeze Airways
Deal found 4/29![Breeze Airways logo]()
$118
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/810:08 pm
ORF
- PVD
Nonstop1h 28m
Breeze Airways
Thu 6/117:30 am
PVD
- ORF
Nonstop1h 33m
Breeze Airways
Deal found 4/30![Breeze Airways logo]()
$118
This Mytrip deal was found by Cheapflights users on 4/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1610:30 pm
ORF
- BDL
Nonstop1h 29m
Breeze Airways
Mon 5/186:00 am
BDL
- ORF
Nonstop1h 31m
Breeze Airways
Deal found 4/29![Breeze Airways logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 5/1012:16 pm
ORF
- HVN
Nonstop1h 23m
Breeze Airways
Thu 5/142:39 pm
HVN
- ORF
Nonstop1h 24m
Breeze Airways
Deal found 4/26![Breeze Airways logo]()
$122
This CheapOair deal was found by Cheapflights users on 4/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/42:16 pm
ORF
- PVD
Nonstop1h 28m
Breeze Airways
Tue 8/184:29 pm
PVD
- ORF
Nonstop1h 33m
Breeze Airways
Deal found 4/30![Breeze Airways logo]()
$122
This CheapOair deal was found by Cheapflights users on 4/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/712:16 pm
ORF
- HVN
Nonstop1h 23m
Breeze Airways
Thu 5/212:39 pm
HVN
- ORF
Nonstop1h 24m
Breeze Airways
Deal found 4/28![Breeze Airways logo]()
$123
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 April 30, 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 April 30, 2026.
This Breeze Airways deal was found by Cheapflights users on 4/25. 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 5/1412:16 pm
ORF
- HVN
Nonstop1h 23m
Breeze Airways
Sun 5/242:39 pm
HVN
- ORF
Nonstop1h 24m
Breeze Airways
Deal found 4/25![Breeze Airways logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:06 pm
ORF
- HVN
2 stops29h 45m
Multiple Airlines
Thu 6/42:34 pm
HVN
- ORF
Nonstop1h 24m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$196
This Super.com deal was found by Cheapflights users on 4/27. 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.
Sun 5/1012:16 pm
ORF
- HVN
Nonstop1h 23m
Breeze Airways
Sun 5/172:39 pm
HVN
- ORF
Nonstop1h 24m
Breeze Airways
Deal found 4/27![Breeze Airways logo]()
$112
This Delta deal was found by Cheapflights users on 4/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/242:42 pm
ORF
- LGA
Nonstop1h 33m
Delta
Sun 7/268:55 pm
LGA
- ORF
Nonstop1h 57m
Delta
Deal found 4/28![Delta logo]()
$229
This United Airlines deal was found by Cheapflights users on 4/26. 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 7/25:44 pm
ORF
- EWR
Nonstop1h 58m
United Airlines
Mon 7/67:59 pm
EWR
- ORF
Nonstop1h 43m
United Airlines
Deal found 4/26![United Airlines logo]()
$229
This Breeze Airways deal was found by Cheapflights users on 4/30. 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.
Thu 5/2812:16 pm
ORF
- HVN
Nonstop1h 23m
Breeze Airways
Sun 5/312:39 pm
HVN
- ORF
Nonstop1h 24m
Breeze Airways
Deal found 4/30![Breeze Airways logo]()
$113
This Expedia deal was found by Cheapflights users on 4/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/169:35 pm
ORF
- EWR
1 stop12h 55m
Frontier
Wed 6/1711:30 am
EWR
- ORF
1 stop9h 10m
Frontier
Deal found 4/25![Frontier logo]()
$250
This Breeze Airways deal was found by Cheapflights users on 4/29. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/412:11 pm
ORF
- HVN
Nonstop1h 23m
Breeze Airways
Sun 6/72:34 pm
HVN
- ORF
Nonstop1h 24m
Breeze Airways
Deal found 4/29![Breeze Airways logo]()
$123
This Southwest deal was found by Cheapflights users on 4/26. 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.
Thu 7/23:30 pm
ORF
- BDL
2 stops8h 45m
Southwest
Wed 8/1212:45 pm
BDL
- ORF
2 stops8h 05m
Southwest
Deal found 4/26![Southwest logo]()
$343
This Breeze Airways deal was found by Cheapflights users on 4/27. 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 5/192:31 pm
ORF
- PVD
Nonstop1h 28m
Breeze Airways
Sun 5/241:56 pm
PVD
- ORF
Nonstop1h 33m
Breeze Airways
Deal found 4/27![Breeze Airways logo]()
$148
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/112:44 pm
ORF
- LGA
Nonstop1h 37m
Delta
Tue 6/168:06 am
LGA
- ORF
Nonstop1h 34m
Delta
Deal found 4/25![Delta logo]()
$229
This Breeze Airways deal was found by Cheapflights users on 4/28. 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.
Tue 6/162:16 pm
ORF
- PVD
Nonstop1h 28m
Breeze Airways
Tue 6/234:29 pm
PVD
- ORF
Nonstop1h 33m
Breeze Airways
Deal found 4/28![Breeze Airways logo]()
$158
This United Airlines deal was found by Cheapflights users on 4/26. 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 5/226:05 am
ORF
- EWR
1 stop3h 47m
United Airlines
Mon 5/257:59 pm
EWR
- ORF
Nonstop1h 43m
United Airlines
Deal found 4/26![United Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 4/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/56:48 pm
ORF
- LGA
Nonstop1h 37m
Delta
Mon 6/84:43 pm
LGA
- ORF
Nonstop1h 40m
Delta
Deal found 4/28![Delta logo]()
$229
This Breeze Airways deal was found by Cheapflights users on 4/28. 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.
Mon 8/178:06 pm
ORF
- BDL
Nonstop1h 29m
Breeze Airways
Sat 8/227:35 am
BDL
- ORF
Nonstop1h 31m
Breeze Airways
Deal found 4/28![Breeze Airways logo]()
$163
This United Airlines deal was found by Cheapflights users on 4/27. 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 5/226:05 am
ORF
- EWR
1 stop3h 47m
United Airlines
Sun 5/247:29 pm
EWR
- ORF
1 stop4h 15m
United Airlines
Deal found 4/27![United Airlines logo]()
$244
This Delta deal was found by Cheapflights users on 4/26. 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 6/86:04 am
ORF
- LGA
Nonstop1h 26m
Delta
Sat 6/1310:20 am
LGA
- ORF
Nonstop1h 39m
Delta
Deal found 4/26![Delta logo]()
$229
This Breeze Airways deal was found by Cheapflights users on 4/27. 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 6/58:06 pm
ORF
- BDL
Nonstop1h 29m
Breeze Airways
Mon 6/86:00 am
BDL
- ORF
Nonstop1h 31m
Breeze Airways
Deal found 4/27![Breeze Airways logo]()
$163
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Thu 5/216:05 am
ORF
- EWR
1 stop3h 51m
United Airlines
Mon 5/257:29 pm
EWR
- ORF
1 stop4h 15m
United Airlines
Deal found 4/29![United Airlines logo]()
$244
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/72:42 pm
ORF
- LGA
Nonstop1h 33m
Delta
Mon 7/138:55 pm
LGA
- ORF
Nonstop1h 57m
Delta
Deal found 4/29![Delta logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 7/212:21 pm
ORF
- BDL
3 stops34h 27m
Multiple Airlines
Wed 8/127:35 am
BDL
- ORF
Nonstop1h 31m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$319
This Breeze Airways deal was found by Cheapflights users on 4/29. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/142:16 pm
ORF
- PVD
Nonstop1h 28m
Breeze Airways
Tue 7/214:29 pm
PVD
- ORF
Nonstop1h 33m
Breeze Airways
Deal found 4/29![Breeze Airways logo]()
$168
This United Airlines deal was found by Cheapflights users on 4/27. 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 5/116:05 am
ORF
- EWR
Nonstop1h 35m
United Airlines
Wed 5/2010:33 am
EWR
- ORF
Nonstop1h 31m
United Airlines
Deal found 4/27![United Airlines logo]()
$249
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:50 pm
ORF
- LGA
Nonstop1h 39m
Delta
Mon 10/124:29 pm
LGA
- ORF
Nonstop1h 36m
Delta
Deal found 4/29![Delta logo]()
$229
This Delta deal was found by Cheapflights users on 4/25. 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 6/106:04 am
ORF
- LGA
Nonstop1h 26m
Delta
Sat 6/1310:20 am
LGA
- ORF
Nonstop1h 39m
Delta
Deal found 4/25![Delta logo]()
$229
This United Airlines deal was found by Cheapflights users on 4/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/55:44 pm
ORF
- EWR
Nonstop1h 58m
United Airlines
Sun 6/76:00 am
EWR
- ORF
1 stop3h 39m
United Airlines
Deal found 4/28![United Airlines logo]()
$252
This Delta deal was found by Cheapflights users on 4/26. 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.
Fri 5/226:43 pm
ORF
- LGA
Nonstop1h 37m
Delta
Mon 5/258:15 am
LGA
- ORF
Nonstop1h 30m
Delta
Deal found 4/26![Delta logo]()
$229
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Thu 6/46:05 am
ORF
- EWR
1 stop3h 51m
United Airlines
Tue 6/95:40 pm
EWR
- ORF
Nonstop1h 42m
United Airlines
Deal found 4/29![United Airlines logo]()
$259
This Breeze Airways deal was found by Cheapflights users on 4/27. 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 6/198:06 pm
ORF
- BDL
Nonstop1h 29m
Breeze Airways
Sun 6/218:00 am
BDL
- ORF
Nonstop1h 31m
Breeze Airways
Deal found 4/27![Breeze Airways logo]()
$198
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/268:00 am
ORF
- LGA
Nonstop1h 30m
Delta
Sun 9/277:45 am
LGA
- ORF
Nonstop1h 34m
Delta
Deal found 4/29![Delta logo]()
$229
Last-minute flights from Chesapeake to ConnecticutDiscover last-minute flight deals from Chesapeake to Connecticut. Data last updated April 30, 2026 and is based on user searches.
Discover last-minute flight deals from Chesapeake to Connecticut. Data last updated April 30, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 4/26. 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 5/610:30 pm
ORF
- BDL
Nonstop1h 29m
Breeze Airways
Sun 5/107:15 am
BDL
- ORF
Nonstop1h 31m
Breeze Airways
Deal found 4/26![Breeze Airways logo]()
$137
This CheapOair deal was found by Cheapflights users on 4/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/712:16 pm
ORF
- HVN
Nonstop1h 23m
Breeze Airways
Thu 5/212:39 pm
HVN
- ORF
Nonstop1h 24m
Breeze Airways
Deal found 4/28![Breeze Airways logo]()
$123
This Super.com deal was found by Cheapflights users on 4/27. 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.
Sun 5/1012:16 pm
ORF
- HVN
Nonstop1h 23m
Breeze Airways
Sun 5/172:39 pm
HVN
- ORF
Nonstop1h 24m
Breeze Airways
Deal found 4/27![Breeze Airways logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 5/1012:16 pm
ORF
- HVN
Nonstop1h 23m
Breeze Airways
Thu 5/142:39 pm
HVN
- ORF
Nonstop1h 24m
Breeze Airways
Deal found 4/26![Breeze Airways logo]()
$122
This Breeze Airways deal was found by Cheapflights users on 4/28. 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.
Wed 5/1310:30 pm
ORF
- BDL
Nonstop1h 29m
Breeze Airways
Thu 5/147:15 am
BDL
- ORF
Nonstop1h 31m
Breeze Airways
Deal found 4/28![Breeze Airways logo]()
$108
This Breeze Airways deal was found by Cheapflights users on 4/25. 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 5/1412:16 pm
ORF
- HVN
Nonstop1h 23m
Breeze Airways
Sun 5/242:39 pm
HVN
- ORF
Nonstop1h 24m
Breeze Airways
Deal found 4/25![Breeze Airways logo]()
$103
This Mytrip deal was found by Cheapflights users on 4/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1610:30 pm
ORF
- BDL
Nonstop1h 29m
Breeze Airways
Mon 5/186:00 am
BDL
- ORF
Nonstop1h 31m
Breeze Airways
Deal found 4/29![Breeze Airways logo]()
$120
This Mytrip deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/192:31 pm
ORF
- PVD
Nonstop1h 28m
Breeze Airways
Sun 5/241:56 pm
PVD
- ORF
Nonstop1h 33m
Breeze Airways
Deal found 4/26![Breeze Airways logo]()
$136
This CheapOair deal was found by Cheapflights users on 4/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/2412:16 pm
ORF
- HVN
Nonstop1h 23m
Breeze Airways
Sun 5/312:39 pm
HVN
- ORF
Nonstop1h 24m
Breeze Airways
Deal found 4/29![Breeze Airways logo]()
$137
This Breeze Airways deal was found by Cheapflights users on 4/28. 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.
Thu 5/2812:16 pm
ORF
- HVN
Nonstop1h 23m
Breeze Airways
Sun 5/312:39 pm
HVN
- ORF
Nonstop1h 24m
Breeze Airways
Deal found 4/28![Breeze Airways logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:16 pm
ORF
- HVN
Nonstop1h 23m
Breeze Airways
Thu 6/42:34 pm
HVN
- ORF
Nonstop1h 24m
Breeze Airways
Deal found 4/29![Breeze Airways logo]()
$118
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:35 pm
ORF
- PVD
Nonstop1h 28m
Breeze Airways
Thu 6/41:56 pm
PVD
- ORF
Nonstop1h 33m
Breeze Airways
Deal found 4/30![Breeze Airways logo]()
$139
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 April 30, 2026.
Search for one-way flight options from Chesapeake to Connecticut. Find affordable one-way fares based on user searches. Data last updated April 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2810:08 pm
ORF
- PVD
Nonstop1h 28m
Breeze Airways
Deal found 4/29![Breeze Airways logo]()
$43
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/712:16 pm
ORF
- HVN
Nonstop1h 23m
Breeze Airways
Deal found 4/28![Breeze Airways logo]()
$49
This Booking.com deal was found by Cheapflights users on 4/30. 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.
Wed 5/2710:30 pm
ORF
- BDL
Nonstop1h 29m
Breeze Airways
Deal found 4/30![Breeze Airways logo]()
$49
This Kiwi.com deal was found by Cheapflights users on 4/27. 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 5/910:30 pm
ORF
- BDL
Nonstop1h 29m
Breeze Airways
Deal found 4/27![Breeze Airways logo]()
$53
This Booking.com deal was found by Cheapflights users on 4/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/810:08 pm
ORF
- PVD
Nonstop1h 28m
Breeze Airways
Deal found 4/29![Breeze Airways logo]()
$57
This CheapOair deal was found by Cheapflights users on 4/27. 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 6/22:31 pm
ORF
- PVD
Nonstop1h 28m
Breeze Airways
Deal found 4/27![Breeze Airways logo]()
$61
This Booking.com deal was found by Cheapflights users on 4/30. 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.
Thu 5/288:35 pm
ORF
- PVD
Nonstop1h 28m
Breeze Airways
Deal found 4/30![Breeze Airways logo]()
$63
This Breeze Airways deal was found by Cheapflights users on 4/28. 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.
Wed 7/110:30 pm
ORF
- BDL
Nonstop1h 29m
Breeze Airways
Deal found 4/28![Breeze Airways logo]()
$64
This CheapOair deal was found by Cheapflights users on 4/26. 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 6/1910:08 pm
ORF
- PVD
Nonstop1h 28m
Breeze Airways
Deal found 4/26![Breeze Airways logo]()
$66
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/612:00 pm
ORF
- LGA
1 stop11h 14m
Frontier
Deal found 4/30![Frontier logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 6/912:21 pm
ORF
- LGA
1 stop10h 53m
Frontier
Deal found 4/26![Frontier logo]()
$70
This CheapOair deal was found by Cheapflights users on 4/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/2412:16 pm
ORF
- HVN
Nonstop1h 23m
Breeze Airways
Deal found 4/29![Breeze Airways logo]()
$71
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 April 30, 2026.
Round-trip from | $103 (Breeze Airways) |
|---|---|
One-way from | $43 (Kiwi.com) |
Popular in | April |
Cheapest in | November |
Average price | $294 |
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 April 30, 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 - HVN
ORFHVN
Norfolk
Thu 5/14
12:16 pm-1:39 pm
Nonstop1h 23m
Tweed-New Haven
Sun 5/24
2:39 pm-4:03 pm
Nonstop1h 24m
$103
NorfolkNew Haven
ORF - HVN
ORFHVN
Norfolk
Sun 5/10
12:16 pm-1:39 pm
Nonstop1h 23m
Tweed-New Haven
Sun 5/17
2:39 pm-4:03 pm
Nonstop1h 24m
$112
NorfolkNew Haven
ORF - HVN
ORFHVN
Norfolk
Thu 5/28
12:16 pm-1:39 pm
Nonstop1h 23m
Tweed-New Haven
Sun 5/31
2:39 pm-4:03 pm
Nonstop1h 24m
$113
NorfolkNew Haven
ORF - HVN
ORFHVN
Norfolk
Thu 6/4
12:11 pm-1:34 pm
Nonstop1h 23m
Tweed-New Haven
Sun 6/7
2:34 pm-3:58 pm
Nonstop1h 24m
$123
NorfolkProvidence
ORF - PVD
ORFPVD
Norfolk
Tue 5/19
2:31 pm-3:59 pm
Nonstop1h 28m
Providence-TFGreen
Sun 5/24
1:56 pm-3:29 pm
Nonstop1h 33m
$148
NorfolkProvidence
ORF - PVD
ORFPVD
Norfolk
Tue 6/16
2:16 pm-3:44 pm
Nonstop1h 28m
Providence-TFGreen
Tue 6/23
4:29 pm-6:02 pm
Nonstop1h 33m
$158
NorfolkHartford
ORF - BDL
ORFBDL
Norfolk
Mon 8/17
8:06 pm-9:35 pm
Nonstop1h 29m
Hartford Bradley Intl
Sat 8/22
7:35 am-9:06 am
Nonstop1h 31m
$163
NorfolkHartford
ORF - BDL
ORFBDL
Norfolk
Fri 6/5
8:06 pm-9:35 pm
Nonstop1h 29m
Hartford Bradley Intl
Mon 6/8
6:00 am-7:31 am
Nonstop1h 31m
$163
NorfolkProvidence
ORF - PVD
ORFPVD
Norfolk
Tue 7/14
2:16 pm-3:44 pm
Nonstop1h 28m
Providence-TFGreen
Tue 7/21
4:29 pm-6:02 pm
Nonstop1h 33m
$168
NorfolkNew Haven
ORF - HVN
ORFHVN
Norfolk
Thu 5/28
12:06 pm-5:51 pm
2 stops29h 45m
Tweed-New Haven
Thu 6/4
2:34 pm-3:58 pm
Nonstop1h 24m
$196
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-HVN
ORF-BDL
ORF-PVD
ORF-LGA
ORF-JFK
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-HVN
ORF-BDL
ORF-PVD
ORF-LGA
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 April 30, 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 45% on airfare.
How much does it cost to fly round-trip from Chesapeake to Connecticut?
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 April 30, 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
Food
6.6
Entertainment
6.6
Boarding
8.3
Crew
8.7
Overall
8.1
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Comfort
8.2
Food
6.6
Entertainment
6.6
Boarding
8.3
Crew
8.7
Overall
8.1
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Comfort
8.2
Food
6.6
Entertainment
6.6
Boarding
8.3
Crew
8.7
Overall
8.1
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Comfort
8.2
Food
6.6
Entertainment
6.6
Boarding
8.3
Crew
8.7
Overall
8.1
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Comfort
8.2
Food
6.6
Entertainment
6.6
Boarding
8.3
Crew
8.7
Overall
8.1
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 April 30, 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 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 April 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$78 | Average$142 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$101 | Average$246 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$156 | Average$321 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$194 | Average$374 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$196 | Average$350 | FlexibilityNo cancel fee | On-time71% |