Cheap flights from Chicago, IL to Key West, FL

One search, all the flights

We find you the best flight deals and travel hacks so that you can choose how to book.

Rise above all travel anxieties

With the Kiwi.com Guarantee we have your back with whatever happens.

Trusted by millions

Join over 10 million yearly travellers booking with ease.

Key info about flying to Key West

Depart from
O Hare International
Arrive to
Key West International
Average flights per week
49
Flight distance
2020 km

Weekly direct flights

Discover the top airlines offering direct flights from Chicago to Key West in the next month. You’ll find the number of daily direct flights per airline in the chart.

AirlineSun 15.12Mon 16.12Tue 17.12Wed 18.12Thu 19.12Fri 20.12Sat 21.12
---------1---1---
---------------------
Weekly flights: 2 totalDaily flights: 0.29 averageMost flights: Wednesday 1 flights
AirlineSun 22.12Mon 23.12Tue 24.12Wed 25.12Thu 26.12Fri 27.12Sat 28.12
1122---22
---------------11
Weekly flights: 12 totalDaily flights: 1.71 averageMost flights: Tuesday 2 flights
AirlineSun 29.12Mon 30.12Tue 31.12Wed 01.01Thu 02.01Fri 03.01Sat 04.01
2222222
------1------1---
Weekly flights: 16 totalDaily flights: 2.29 averageMost flights: Sunday 2 flights
AirlineSun 05.01Mon 06.01Tue 07.01Wed 08.01Thu 09.01Fri 10.01Sat 11.01
1111111
------111------
Weekly flights: 10 totalDaily flights: 1.43 averageMost flights: Sunday 1 flights

Check-in for a flight from Chicago to Key West

NameCarrier codeIATA CodePassport needed during booking
American AirlinesAALAANo
United AirlinesUALUAYes

Weather in Key West

Average Weather

MonthAverage monthly max temperatureAverage monthly min temperature
January22°C20°C
February23°C21°C
March23°C22°C
April25°C24°C
May26°C25°C
June28°C27°C
July29°C28°C
August29°C28°C
September29°C28°C
October27°C26°C
November25°C24°C
December24°C22°C
Hottest Month
29°C
August
Coldest month
20°C
January
Sunny days
294
days per year

14 day forecast

Monday
16 Dec
23°C21°C
23 Dec
73%
22°C21°C
Tuesday
17 Dec
25°C22°C
24 Dec
88%
22°C22°C
Wednesday
18 Dec
23°C23°C
25 Dec
22°C21°C
Thursday
19 Dec
22°C22°C
26 Dec
87%
23°C22°C
Friday
20 Dec
22°C20°C
27 Dec
23°C23°C
Saturday
21 Dec
19°C17°C
28 Dec
82%
23°C22°C
Sunday
22 Dec
20°C19°C
29 Dec
89%
23°C22°C

Travel tips & how to get from Chicago to Key West

The cheapest price of a one-way ticket from Chicago to Key West is $145. Round trip fares cost between $345 at the lowest and $1,359 at most.
Travelers usually depart from O Hare International, Chicago Midway International, or Chicago Rockford International when they travel from Chicago to Key West. The distance between Chicago and Key West is 2020 km. The most popular airlines for this route are American Airlines, and United Airlines. Chicago and Key West have 49 direct flights per week.

Frequently asked questions

How long does it take to travel from Chicago to Key West?
What is the flight distance between Chicago and Key West?
What airlines offer nonstop (direct) flights between Chicago and Key West?
What are the most popular routes to and from Chicago?
What are the most popular routes to and from Key West?
What airports are near Key West?
Which airlines fly between Chicago and Key West?
When's the best time to travel between Chicago and Key West?
What flights operate between Chicago and Key West?
How many airports are there near Key West?
What time do nonstop (direct) flights between Chicago and Key West depart?
What time do nonstop (direct) flights between Chicago and Key West arrive?
What time do flights between Chicago and Key West depart?
What time do flights between Chicago and Key West arrive?

Explore alternative trips

Flights from Chicago

Flights to Key West

Popular routes

The nearest countries with flights to Key West

Here is a list of countries people are flying from

Other destination countries from Chicago

Here is a list of countries people are flying to
Find the best connection from Chicago to Key West
Search flights

Get more out of Kiwi.com with our mobile application

Download boarding passes

One-click booking

Get exclusive offers and prices

Mobile trip notifications

We hack the system,
you fly for less