Cheap Flights from Chicago, IL to Key West, FL from $104
On Cheapflightsplus.com you will find 241 connecting flights from Chicago to Key West. You can compare airfare deals from 4 airlines and multiple travel sites from $104, book and save on cheap plane tickets and last minute offers. Also check out CHI-EYW flight schedule to find best flight time, convenient departure and arrival airports.
Flight Information
Below we will explain in detail what the flights cost on the destination from Chicago to Key West depends on and how to choose the most interesting flight option for you.
Distance between Chicago and Key West is 2001 miles. Time difference between the cities is 1h. Airplanes depart 05:05 to 21:45 from 7 Chicago airports and arrive 05:05 to 21:45 to 2 Key West airports. Average flight time is 22h 27m.
- The fastest flight 5h 30m
- Average flight time 22h 27m
- The earliest flight 05:05
- The latest flight 21:45
- Distance 1244 ml
Best Flights from Chicago to Key West Today
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $104 | 19:39 Chicago O'Hare International | 14:10+1 день Key West Key West Int. | 17h 31m layover 13h 28m - Sanford | Spirit Airlines | NK507 G41340 |
| from $129 | 16:38 Chicago O'Hare International | 14:43+1 день Key West Key West Int. | 21h 5m layover 17h 13m - Clearwater | Spirit Airlines | NK529 G41034 |
| from $140 | 15:29 Chicago O'Hare International | 14:10+1 день Key West Key West Int. | 21h 41m layover 2h 9m - Miami 14h 0m - Sanford | Spirit Airlines | NK867 NK676 G41340 |
| from $148 | 20:36 Chicago Midway | 15:03+1 день Key West Key West Int. | 17h 27m layover 6h 47m - Fletcher 6h 23m - Clearwater | Allegiant Air | G4248 G4247 G41071 |
The cheapest months to travel to Key West are august (from 104 $), june (from 140 $), july (from 150 $).
The most expensive months are november (from 530 $), january (from 399 $), december (from 351 $).
What is the lowest airfare Chicago to Key West?
The cheapest plane ticket found by our users is $104. This airfare is for economy class on one-way NK507 flight by Spirit Airlines for August 16, 2025 which leaves O'Hare International in Chicago at 19:39 am and arrives at Key West Key West Int. at 14:10.
Flight Schedule Chicago (Illinois) to Key West (Florida)
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Popular Airlines on the Route
The flight Chicago — Key West is served by 4 regular airlines and 3 low-cost airlines. Most of the flights on this route are operated by Sun Country Airlines - 7 departures per week at the price of from $ 205 . And the most expensive tickets are offered by United Airlines airline - from $ 1245.
Direct flights
There’re no direct flights on this route. Try flights with stops.
Connecting Flights
There are 241 flights with layovers on the route. The fastest connecting flight is UA2326 by United Airlines takes 5h 30m and the cheapest is NK507 by Spirit Airlines for $104.
- SY - Sun Country Airlinesfrom $205Find
- UA - United Airlinesfrom $195Find
- NK - Spirit Airlinesfrom $104Find
- G4 - Allegiant Airfrom $148Find
Airports
You can fly from Chicago to Key West from 7 airports (O'Hare International, Midway, Dupage County, Chicago FSS, Merrill C Meigs (closed), Pal-Waukee, Chicago NAS).
Chicago airports
- O'Hare International-ORDfrom $104Find
- Midway-MDWfrom $148Find
- Dupage County-DPAFind
- Chicago FSS-CHIFind
- Merrill C Meigs (closed)-CGXFind
- Pal-Waukee-PWKFind
- Chicago NAS-NOHFind
Key West airports
- NAS-NQXFind
- Key West Int.-EYWFind
Airplanes
There are flights to Key West from Chicago by 4 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.
Top Domestic Destinations from Chicago
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Top International Destinations from Chicago
Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.
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How to book a plane ticket yourself?
- Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
- Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
- Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
- Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
- That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.
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