Flights from Chicago to Key West
North AmericaYear-round

Cheap Flights from Chicago to Key West

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

From
Chicago
ORD
To
Key West
EYW

Route Intelligence: Chicago → Key West

Flight Duration

3 hr 15 min (Direct)

Price Guidance

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

Peak Season

Nov-Mar

Top Airlines

American Airlines, United Airlines

Booking Tip

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

Track Chicago → 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.

Start Tracking — Free 7-Day Trial

Route Summary: Chicago → Key West

From
Chicago (ORD)
To
Key West (EYW)
Duration
3 hr 15 min (Direct)
Airlines
American Airlines, 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.

Get a Free Quote
Also available: BestBusinessClass.com

Other Routes to Key West

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

More Destinations in North America

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

Route Briefing: Chicago to Key West

Escaping Chicago for the laid-back warmth of the Florida Keys takes 3 hours and 15 minutes on a direct 1,254-mile flight. American and United operate direct flights into Key West International Airport (EYW), whisking travelers to America's southernmost paradise in one quick flight.

Key West operates on easygoing island time, where pastel Victorian conch houses and tropical breezes set a charming tone. Rent a cruiser bicycle to pedal through Old Town, visit Ernest Hemingway's historic home, and join the lively sunset celebration at Mallory Square with street acrobats and musicians. Feast on fresh pink shrimp, conch fritters, and a slice of tart key lime pie from Kermit's on Elizabeth Street.

Economy roundtrips under $180 are a great catch, with standard pricing typically landing between $280 and $420. High season runs from November through April when winter travelers escape the cold. Book 6 to 10 weeks out for the best economy seat availability.

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

Flight prices from Chicago (ORD) 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, 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 Chicago to Key West fares?

FlightKitten is an economy flight price monitoring platform that scans 220+ airlines twice every day for economy fares on the ORD 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: Chicago 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.