Cheap flights to Key West
Set your departure airport and your maximum budget: SniperAir tracks prices to Key West and alerts you the moment an opportunity matching your criteria appears.
Quick summary
Country
United States
Continent
North America
Airport
EYW
Currency
US dollar (USD)
Time zone
UTC-5
Opportunities already detected to Key West
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History
From Spanish claim to Cuban cigar town
First claimed by Spain in 1565 and sold to an American buyer in 1822, Key West has flown Spanish, British and American flags in turn, and its population still carries that mixed heritage. From the early 1830s, Cuban migrants — including scores of skilled cigar rollers — began settling on the island just 90 miles from Havana, and several of their former cigar factories and worker cottages still stand today. In 1892, Cuban independence leader José Martí delivered one of his best-known speeches from the balcony of the San Carlos Institute on Duval Street, a building that still honors that Cuban-American history.
Identity
The southernmost point of the continental United States
In 1983, the city planted a 20-ton striped concrete buoy near the corner of Whitehead and South Street, marked "Southernmost Point Continental U.S.A." — 90 miles from Cuba — and it has been drawing photo lines ever since, even though the actual southernmost spot on the island sits on nearby (closed) Navy land. Locals sometimes call the island the "Conch Republic," a nod to a tongue-in-cheek 1982 mock secession staged to protest a federal highway checkpoint, and the nickname has stuck as shorthand for Key West's famously laid-back, anything-goes atmosphere — a world away from mainland Florida just a few hours' drive north.
To discover
Duval Street and the Hemingway House
Duval Street cuts across the island from the Gulf to the Atlantic, lined with bars, galleries and shops, and running past the Key West Lighthouse and the house where Ernest Hemingway lived with his second wife, Pauline, from 1931 until their 1940 divorce. Built in 1851 out of native limestone by marine salvager Asa Tift, the two-story home is where an estimated 70% of Hemingway's published work was written; it is now the island's most-visited attraction, both for the writer's legacy and for the roughly 50 to 60 polydactyl, six-toed cats that live on the grounds, descended from one given to Hemingway by a ship's captain.
Not to be missed
Sunset Celebration at Mallory Square
Every evening since the 1960s, street performers, musicians, fortune tellers and food carts fill Mallory Square roughly two hours before sunset, building toward the moment the sun drops into the Gulf of Mexico — a nightly tradition often credited, informally, to playwright Tennessee Williams having been among the first to applaud the sunset here. It draws a genuine mix of visitors and locals rather than a staged show, and it's free to attend, though tips for performers are customary.
Food
Key lime pie, a dessert with a disputed origin
No one can say for certain who baked the first Key lime pie: the popular story credits "Aunt Sally," a cook for Key West's first millionaire William Curry, but that account only surfaces in print from the 1990s. Food historians point instead to late-19th-century sponge fishermen or cooks who combined the tart local Key lime with sweetened condensed milk — a practical choice on an island where fresh milk and refrigeration were scarce before the 1930s. Whatever its true origin, the tangy, custard-like pie with a graham-cracker crust is now sold everywhere on the island, from waterfront restaurants to small bakeries just off Duval Street.
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Getting there
EYW: a small airport, and the long way in by road
Key West International
A compact single-terminal airport handling around one million passengers a year, with nonstop flights from roughly 20 domestic destinations — a fraction of Miami's traffic, but with the runway to match: no widebody jets land here.
Most itineraries from Europe connect through Miami or another major US hub before the short final hop to EYW. Driving in instead means following the Overseas Highway (US Route 1) roughly 160 miles and about 4 hours from Miami, crossing 42 bridges including the 7-mile span over open water — one of the most scenic drives in the country, and reason enough on its own for some travelers to fly into Miami and rent a car. Price data for Key West is still limited: SniperAir has only just started tracking this route.
When to go
When to visit Key West?
Spring
The dry season winds down; warm and increasingly humid, before the summer heat sets in fully.
Summer
Hot and humid, with afternoon storms and the peak of the official hurricane season (June through November).
Autumn
Hurricane risk remains through November, but crowds and prices both drop noticeably.
Winter
Peak season: dry, mild and sunny, drawing travelers escaping colder climates further north.
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FAQ
Frequently asked questions about flights to Key West
What is Key West's airport?
Key West International (EYW), a small single-terminal airport at the southern end of the Keys with nonstop flights from around 20 US cities — most connections from Europe route through Miami first.
How much does a flight to Key West usually cost?
SniperAir has only just started tracking this route and doesn't yet have enough history for a reliable price range. Create an alert to be notified as soon as a price is detected.
Is it better to fly directly into Key West or drive from Miami?
Both work: flying into EYW is faster but often pricier for the last leg, while driving the Overseas Highway from Miami takes about 4 hours over roughly 160 miles and is considered one of the most scenic road trips in the US.
Why is Key West called the southernmost point of the continental US?
A striped concrete marker near Whitehead and South Street has stated this since 1983, 90 miles from Cuba. The technical southernmost spot on the island sits on nearby restricted land, but the buoy remains the point everyone visits.
What is the Sunset Celebration at Mallory Square?
A free, nightly street-performance tradition dating to the 1960s: musicians, acrobats and vendors gather roughly two hours before sunset, building toward the moment the sun sets over the Gulf of Mexico.
What should I prioritize in Key West with just one day?
Duval Street and the Hemingway House in the morning or afternoon, then Mallory Square for the Sunset Celebration in the early evening.
How do I get alerted when a flight to Key West drops below my budget?
Create an alert profile with your departure airport, Key West as the destination, and your maximum budget. You'll be notified automatically as soon as a matching price is detected.
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