Flights from Boston to Key West
North AmericaYear-round

Cheap Flights from Boston to Key West

Track economy fares on the BOS → EYW route and get alerts when prices drop.

From
Boston
BOS
To
Key West
EYW

Route Intelligence: Boston → Key West

Flight Duration

3 hr 30 min (Direct)

Price Guidance

A good deal is under $250 roundtrip. Standard fare is $350–$500+.

Peak Season

Nov-Mar

Top Airlines

American Airlines, Delta Air Lines, United Airlines

Booking Tip

Book 1-3 months in advance for the best domestic fares.

Track Boston → Key West Fares

Set your target price and FlightKitten will scan this route twice daily. The instant economy fares drop below your budget, you'll get an email with the price, airline, and a direct booking link.

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Route Summary: Boston → Key West

From
Boston (BOS)
To
Key West (EYW)
Duration
3 hr 30 min (Direct)
Airlines
American Airlines, Delta Air Lines, United Airlines
Price Guide
A good deal is under $250 roundtrip. Standard fare is $350–$500+.
Tracking
FlightKitten scans 220+ airlines 2× daily
220+
Airlines Monitored
2×
Daily Scanning
AI
Deal Briefings
7-Day
Free Trial
Premium Cabin

Prefer business class on this route?

CEOFLIGHTSon board with your vision

Everyone deserves comfort at an affordable price. CEOFLIGHTS Personal Travel Managers find you the best business class fares and handle every detail of your journey.

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Also available: BestBusinessClass.com

Other Routes to Key West

New York→Key WestLos Angeles→Key WestChicago→Key WestMiami→Key WestSan Francisco→Key WestSeattle→Key West

More Destinations in North America

Anchorage
Anchorage
Atlanta
Atlanta
Austin
Austin
Boston
Boston
Charleston
Charleston
Charlotte
Charlotte

Route Briefing: Boston to Key West

Escaping Boston for the laid-back charm of the Florida Keys takes about 3 hours and 30 minutes over 1,375 miles. Major carriers like American, Delta, and United provide direct and easy one-stop flights into Key West International Airport (EYW), placing you right in the heart of tropical paradise.

Key West offers a wonderfully eccentric island atmosphere where roosters roam past Victorian conch houses. Rent a bicycle to explore Old Town, tour Ernest Hemingway's historic home, and join the lively sunset celebration at Mallory Square featuring street acrobats and musicians. Enjoy fresh conch fritters, peel-and-eat pink shrimp, and a slice of tart key lime pie while listening to live acoustic music along Duval Street.

Roundtrip economy fares under $190 are a solid deal, with standard fares ranging from $290 to $440. Peak season runs from November through April when winter travelers seek warm sunshine and calm turquoise waters. Book 6 to 10 weeks ahead for the best economy ticket savings.

How much are flights from Boston to Key West in 2026?

Flight prices from Boston (BOS) to Key West (EYW) vary significantly depending on the season, day of the week, and how far in advance you book. A good deal is under $250 roundtrip. Standard fare is $350–$500+. Popular carriers on this route include American Airlines, Delta Air Lines, United Airlines. FlightKitten eliminates the guesswork by monitoring 220+ airlines twice daily and alerting you the moment economy fares hit your target price.

How does FlightKitten track Boston to Key West fares?

FlightKitten is an economy flight price monitoring platform that scans 220+ airlines twice every day for economy fares on the BOS to EYW route. When you set a target price, FlightKitten continuously monitors this route and sends an email alert the moment fares drop below your budget. Each alert includes the exact fare, airline, dates, and an AI-powered briefing that explains whether the deal is genuinely good compared to historical pricing on this route. No more obsessive price checking — set your budget and let FlightKitten do the watching. Learn more about how FlightKitten tracking works.

See our full Key West destination guide for all available routes. Also popular: Boston to Anchorage.

Pro tip: Book 1-3 months in advance for the best domestic fares.

Looking for business class on this route? CEOFLIGHTS pairs you with a Personal Travel Manager who finds affordable business class fares and handles every detail of your journey. Alternatively, BestBusinessClass.com offers free expert quotes with real savings.