$82+ Cheap flights from Connecticut to Key West (EYW)
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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — EYW
Dec 8 — Dec 151
Round-trip
1 adult, Economy
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Find cheap flights from Connecticut to Key West with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Connecticut to Key West
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Cheapest flights from Connecticut to Key WestExplore the most affordable flight options available from Connecticut to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 8, 2026.
Explore the most affordable flight options available from Connecticut to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 8, 2026.
This CheapOair deal was found by Cheapflights users on 11/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/212:40 pm -
Nonstop3h 27m
Wed 11/256:52 pm -
Nonstop3h 13m
Deal found 11/6![Avelo Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Wed 12/166:00 am -
1 stop28h 19m
Fri 12/2512:59 pm -
1 stop4h 55m
Deal found 11/3![Breeze Airways logo]()
$229
This Breeze Airways deal was found by Cheapflights users on 11/4. 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.
Fri 11/277:00 am -
1 stop26h 24m
Fri 12/412:59 pm -
1 stop4h 55m
Deal found 11/4![Breeze Airways logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 11/178:10 am -
1 stop25h 14m
Tue 11/2411:04 am -
1 stop11h 20m
Deal found 11/5![Breeze Airways logo]()
$266
This Breeze Airways deal was found by Cheapflights users on 11/6. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/147:00 am -
1 stop5h 19m
Fri 12/1810:59 am -
1 stop25h 55m
Deal found 11/6![Breeze Airways logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 12/107:05 am -
1 stop11h 27m
Tue 12/1510:59 am -
1 stop25h 55m
Deal found 11/6![Multiple Airlines logo]()
$272
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Mon 12/217:00 am -
1 stop5h 19m
Fri 12/2512:59 pm -
1 stop4h 55m
Deal found 11/3![Breeze Airways logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Wed 12/166:00 am -
1 stop28h 19m
Thu 12/2410:59 am -
2 stops12h 37m
Deal found 11/3![Breeze Airways logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/197:10 am -
1 stop28h 11m
Fri 12/2512:59 pm -
1 stop4h 55m
Deal found 11/3![Breeze Airways logo]()
$278
This Trip.com deal was found by Cheapflights users on 11/7. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/207:54 pm -
1 stop14h 25m
Wed 12/307:02 pm -
Nonstop3h 13m
Deal found 11/7![Multiple Airlines logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 11/7. 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 12/207:54 pm -
1 stop14h 25m
Thu 12/3112:01 pm -
2 stops22h 22m
Deal found 11/7![Breeze Airways logo]()
$370
This Kiwi.com deal was found by Cheapflights users on 11/7. 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 12/177:54 pm -
1 stop14h 25m
Thu 12/3112:01 pm -
2 stops22h 22m
Deal found 11/7![Breeze Airways logo]()
$374
Best flights from Connecticut to Key WestDiscover carefully curated flight deals from Connecticut to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 8, 2026.
Discover carefully curated flight deals from Connecticut to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 8, 2026.
This Breeze Airways deal was found by Cheapflights users on 11/6. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/147:00 am -
1 stop5h 19m
Fri 12/1810:59 am -
1 stop25h 55m
Deal found 11/6![Breeze Airways logo]()
$271
This United Airlines deal was found by Cheapflights users on 11/7. 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 12/176:00 am -
2 stops11h 11m
Mon 12/2112:22 pm -
2 stops11h 24m
Deal found 11/7![United Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 11/6. 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.
Tue 12/227:05 am -
1 stop6h 50m
Fri 12/252:50 pm -
1 stop5h 11m
Deal found 11/6![Delta logo]()
$414
This Breeze Airways deal was found by Cheapflights users on 11/7. 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.
Sun 12/612:04 pm -
1 stop23h 15m
Fri 12/1110:59 am -
1 stop25h 55m
Deal found 11/7![Breeze Airways logo]()
$285
This Gotogate deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/138:50 am -
Nonstop3h 37m
Wed 2/1712:19 pm -
2 stops28h 43m
Deal found 11/8![Multiple Airlines logo]()
$619
This Breeze Airways deal was found by Cheapflights users on 11/5. 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 11/277:00 am -
1 stop5h 19m
Fri 12/410:59 am -
2 stops11h 27m
Deal found 11/5![Breeze Airways logo]()
$301
This Breeze Airways deal was found by Cheapflights users on 11/8. 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 2/276:00 am -
1 stop5h 39m
Tue 3/210:59 am -
1 stop28h 05m
Deal found 11/8![Breeze Airways logo]()
$311
This Breeze Airways deal was found by Cheapflights users on 11/8. 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 1/17:00 am -
1 stop5h 19m
Tue 1/510:59 am -
1 stop25h 57m
Deal found 11/8![Breeze Airways logo]()
$324
This Breeze Airways deal was found by Cheapflights users on 11/5. 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 4/303:25 pm -
2 stops18h 51m
Wed 5/512:22 pm -
1 stop24h 24m
Deal found 11/5![Breeze Airways logo]()
$398
This Breeze Airways deal was found by Cheapflights users on 11/3. 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.
Thu 1/212:36 pm -
2 stops19h 43m
Sun 1/2410:59 am -
2 stops27h 34m
Deal found 11/3![Breeze Airways logo]()
$404
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/1211:25 am -
2 stops21h 35m
Mon 3/1511:59 am -
1 stop6h 05m
Deal found 11/4![Multiple Airlines logo]()
$660
This Breeze Airways deal was found by Cheapflights users on 11/8. 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 12/77:00 am -
1 stop5h 19m
Sat 12/1210:45 am -
1 stop26h 24m
Deal found 11/8![Breeze Airways logo]()
$418
This Breeze Airways deal was found by Cheapflights users on 11/4. 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.
Mon 3/292:41 pm -
2 stops20h 35m
Tue 4/611:56 am -
1 stop24h 49m
Deal found 11/4![Breeze Airways logo]()
$424
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:34 pm -
2 stops38h 50m
Mon 11/2311:59 am -
1 stop6h 05m
Deal found 11/4![Breeze Airways logo]()
$495
This KAYAK deal was found by Cheapflights users on 11/6. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/207:54 pm -
1 stop14h 25m
Thu 12/2412:01 pm -
2 stops22h 22m
Deal found 11/6![Breeze Airways logo]()
$613
This KAYAK deal was found by Cheapflights users on 11/3. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/226:34 pm -
2 stops22h 21m
Thu 12/2410:59 am -
1 stop8h 15m
Deal found 11/3![Breeze Airways logo]()
$682
This KAYAK deal was found by Cheapflights users on 11/3. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/107:54 pm -
1 stop14h 25m
Thu 12/1710:59 am -
1 stop8h 15m
Deal found 11/3![Breeze Airways logo]()
$695
This KAYAK deal was found by Cheapflights users on 11/3. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/206:34 pm -
2 stops17h 45m
Sat 12/265:35 pm -
2 stops24h 19m
Deal found 11/3![Breeze Airways logo]()
$719
This KAYAK deal was found by Cheapflights users on 11/4. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/186:44 pm -
2 stops22h 11m
Wed 12/305:35 pm -
2 stops24h 19m
Deal found 11/4![Breeze Airways logo]()
$729
This Booking.com deal was found by Cheapflights users on 11/5. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/1811:25 am -
3 stops25h 11m
Fri 1/2211:59 am -
1 stop6h 05m
Deal found 11/5![Breeze Airways logo]()
$738
This KAYAK deal was found by Cheapflights users on 11/5. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/285:42 pm -
2 stops18h 37m
Mon 2/110:59 am -
2 stops7h 05m
Deal found 11/5![Breeze Airways logo]()
$758
Last-minute flights from Connecticut to Key WestDiscover last-minute flight deals from Connecticut to Key West. Data last updated November 8, 2026 and is based on user searches.
Discover last-minute flight deals from Connecticut to Key West. Data last updated November 8, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 11/178:10 am -
1 stop25h 14m
Tue 11/2411:04 am -
1 stop11h 20m
Deal found 11/5![Breeze Airways logo]()
$266
This CheapOair deal was found by Cheapflights users on 11/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/212:40 pm -
Nonstop3h 27m
Wed 11/256:52 pm -
Nonstop3h 13m
Deal found 11/6![Avelo Airlines logo]()
$148
This Breeze Airways deal was found by Cheapflights users on 11/4. 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.
Fri 11/277:00 am -
1 stop26h 24m
Fri 12/412:59 pm -
1 stop4h 55m
Deal found 11/4![Breeze Airways logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 12/107:05 am -
1 stop11h 27m
Tue 12/1510:59 am -
1 stop25h 55m
Deal found 11/6![Multiple Airlines logo]()
$272
This Breeze Airways deal was found by Cheapflights users on 11/6. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/147:00 am -
1 stop5h 19m
Fri 12/1810:59 am -
1 stop25h 55m
Deal found 11/6![Breeze Airways logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Wed 12/166:00 am -
1 stop28h 19m
Fri 12/2512:59 pm -
1 stop4h 55m
Deal found 11/3![Breeze Airways logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Wed 12/166:00 am -
1 stop28h 19m
Thu 12/2410:59 am -
2 stops12h 37m
Deal found 11/3![Breeze Airways logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 11/7. 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 12/177:54 pm -
1 stop14h 25m
Thu 12/3112:01 pm -
2 stops22h 22m
Deal found 11/7![Breeze Airways logo]()
$374
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/197:10 am -
1 stop28h 11m
Fri 12/2512:59 pm -
1 stop4h 55m
Deal found 11/3![Breeze Airways logo]()
$278
This Trip.com deal was found by Cheapflights users on 11/7. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/207:54 pm -
1 stop14h 25m
Wed 12/307:02 pm -
Nonstop3h 13m
Deal found 11/7![Multiple Airlines logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 11/7. 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 12/207:54 pm -
1 stop14h 25m
Thu 12/3112:01 pm -
2 stops22h 22m
Deal found 11/7![Breeze Airways logo]()
$370
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Mon 12/217:00 am -
1 stop5h 19m
Fri 12/2512:59 pm -
1 stop4h 55m
Deal found 11/3![Breeze Airways logo]()
$274
One-way flights from Connecticut to Key WestSearch for one-way flight options from Connecticut to Key West. Find affordable one-way fares based on user searches. Data last updated November 8, 2026.
Search for one-way flight options from Connecticut to Key West. Find affordable one-way fares based on user searches. Data last updated November 8, 2026.
This Expedia deal was found by Cheapflights users on 11/8. 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.
Wed 1/137:00 am -
Nonstop3h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Avelo Airlines logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 1/3112:36 pm -
1 stop22h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Breeze Airways logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Mon 1/116:39 pm -
2 stops40h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Breeze Airways logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Sun 1/107:15 am -
2 stops27h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Breeze Airways logo]()
$150
This Orbitz deal was found by Cheapflights users on 11/8. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/177:30 am -
Nonstop3h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Avelo Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/226:39 pm -
2 stops20h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Multiple Airlines logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Fri 1/156:39 pm -
2 stops39h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Breeze Airways logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Mon 1/1110:45 am -
1 stop23h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Multiple Airlines logo]()
$179
This Travelocity deal was found by Cheapflights users on 11/5. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/173:10 pm -
Nonstop3h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Avelo Airlines logo]()
$183
This Breeze Airways deal was found by Cheapflights users on 11/3. 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.
Thu 1/212:36 pm -
2 stops19h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Breeze Airways logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/1512:03 pm -
3 stops46h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Breeze Airways logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 1/16:02 am -
1 stop29h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Multiple Airlines logo]()
$197
Find flight deals from Connecticut to Key West
Keep the following information in mind while searching for Connecticut to Key West flight deals. Data was last updated November 8, 2026.
Round-trip from | $148 (CheapOair) |
|---|---|
One-way from | $82 (Expedia) |
Popular in | October |
Cheapest in | September |
Average price | $582 |
Cheapflights Fare Finder
Customize your flight search to find flights from Connecticut to Key West 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 November 8, 2026.
Use the filters below to find and compare flights from Connecticut to Key West that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
New HavenKey West
HVN Tweed-New Haven - EYW Key West
HVNEYW
Tweed-New Haven
Wed 1/13
7:00 am-10:37 am
Nonstop3h 37m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$82
HartfordKey West
BDL Hartford Bradley Intl - EYW Key West
BDLEYW
Hartford Bradley Intl
Sun 1/10
12:36 pm-11:19 am
1 stop22h 43m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$162
HartfordKey West
BDL Hartford Bradley Intl - EYW Key West
BDLEYW
Hartford Bradley Intl
Mon 1/11
10:45 am-10:19 am
1 stop23h 34m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$179
Quickest round-trip
New HavenKey West
HVN Tweed-New Haven - EYW Key West
HVNEYW
Tweed-New Haven
Wed 3/17
3:10 pm-6:26 pm
Nonstop3h 16m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$183
New HavenKey West
HVN Tweed-New Haven - EYW Key West
HVNEYW
Tweed-New Haven
Fri 1/15
12:03 pm-10:19 am
3 stops46h 16m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$190
New HavenKey West
HVN Tweed-New Haven - EYW Key West
HVNEYW
Tweed-New Haven
Wed 2/10
8:50 am-12:27 pm
Nonstop3h 37m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$203
HartfordKey West
BDL Hartford Bradley Intl - EYW Key West
BDLEYW
Hartford Bradley Intl
Fri 1/1
6:39 pm-4:55 pm
2 stops22h 16m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$221
HartfordKey West
BDL Hartford Bradley Intl - EYW Key West
BDLEYW
Hartford Bradley Intl
Fri 1/22
7:00 am-12:19 pm
1 stop5h 19m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$226
HartfordKey West
BDL Hartford Bradley Intl - EYW Key West
BDLEYW
Hartford Bradley Intl
Thu 2/18
7:04 pm-11:57 am
1 stop16h 53m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$238
HartfordKey West
BDL Hartford Bradley Intl - EYW Key West
BDLEYW
Hartford Bradley Intl
Mon 12/14
7:00 am-12:19 pm
1 stop5h 19m
Key West
Fri 12/18
10:59 am-12:54 pm
1 stop25h 55m
$271
Showing 1-10 of 40 resultsSorted by cheapest first
Best time to book a flight from Connecticut to Key West
Have a flexible travel schedule? Discover the best time to fly to Key West from Connecticut with our price prediction graph.
HVN-EYW
BDL-EYW
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 Connecticut to Key West
USCT-EYW
HVN-EYW
BDL-EYW
What is the cheapest month to book a flight from Connecticut to Key West?
Currently, September is the cheapest month in which you can book a flight from Connecticut to Key West (average of $345). Flying from Connecticut to Key West in October is currently the most expensive (average of $608). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from Connecticut to Key West?
Airfare is below average for this route at the moment.
Connecticut to Key West flights typically cost between $473 and $792 in November.The cheapest round-trip price found within the last 5 days was $253 on Breeze Airways (Nov 27-Dec 4).
How far ahead should I book a flight from Connecticut to Key West?
The best time to book flights from Connecticut to Key West is 69 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Related info for your journey
Find useful and relevant information for your journey from Connecticut to Key West. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Connecticut to Key West
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Complete your trip
Complete your trip to Key West by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Connecticut to Key West by cabin class
Find flights from Connecticut to Key West, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Key West
Explore flights to Key West departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on November 8, 2026.
Connecticut and Key West flights
Browse other Connecticut and Key West flight options. Last updated on November 8, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Connecticut to Key West flights
Consider these flights traveling from Connecticut to Key West.
Top 5 airlines flying from Connecticut to Key West
Discover the top 5 airlines that operate flights from Connecticut to Key West. 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 November 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$155 | Average$234 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$202 | Average$340 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$283 | Average$505 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$322 | Average$465 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$338 | Average$452 | FlexibilityNo cancel fee | On-time69% |