Flights from Chicago to Key West

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Chicago to Key West flight comparison made easy

Below you can see the best fares for your route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Chicago to Key West by changing tabs
Quickest
Cheapest
American Airlines
American Airlines
02 Nov
ORD
11:40 am
Chicago O'Hare Intl airport
5h 10m
1 Stop
5:50 pm
EYW
Key West airport
American Airlines
05 Nov
EYW
1:40 pm
Key West airport
5h 48m
1 Stop
6:28 pm
ORD
Chicago O'Hare Intl airport
274 USD
American Airlines
American Airlines
02 Nov
ORD
11:40 am
Chicago O'Hare Intl airport
5h 10m
1 Stop
5:50 pm
EYW
Key West airport
American Airlines
05 Nov
EYW
1:40 pm
Key West airport
5h 48m
1 Stop
6:28 pm
ORD
Chicago O'Hare Intl airport
274 USD
American Airlines
American Airlines
09 Dec
ORD
9:10 am
Chicago O'Hare Intl airport
6h 42m
1 Stop
4:52 pm
EYW
Key West airport
American Airlines
12 Dec
EYW
1:40 pm
Key West airport
5h 49m
1 Stop
6:29 pm
ORD
Chicago O'Hare Intl airport
274 USD
United Airlines
United Airlines
15 Jan
ORD
1:35 am
Chicago O'Hare Intl airport
3h 14m
5:49 am
EYW
Key West airport
United Airlines
22 Jan
EYW
2:05 pm
Key West airport
5h 52m
1 Stop
6:57 pm
ORD
Chicago O'Hare Intl airport
364 USD
United Airlines
United Airlines
15 Jan
ORD
1:35 am
Chicago O'Hare Intl airport
3h 14m
5:49 am
EYW
Key West airport
United Airlines
22 Jan
EYW
2:05 pm
Key West airport
5h 52m
1 Stop
6:57 pm
ORD
Chicago O'Hare Intl airport
364 USD
Delta
Delta
16 Sep
ORD
2:20 am
Chicago O'Hare Intl airport
4h 30m
1 Stop
7:50 am
EYW
Key West airport
Delta
25 Sep
EYW
3:00 am
Key West airport
5h 04m
1 Stop
7:04 am
ORD
Chicago O'Hare Intl airport
372 USD

How to get the cheapest flight from Chicago to Key West

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight for your trip
What is the cheapest month to fly to Key West?
September
The cheapest time of year to fly to Key West from Chicago is September. Most expensive is December
What is the cheapest day to fly to Key West?
Tuesday
The cheapest day of the week is typically Tuesday. The most expensive is typically Thursday
When is the cheapest time to fly to Key West?
in the evening
Chicago to Key West flights are approximately 31% more expensive in the morning than in the evening
What is the cheapest airline that flies to Key West?
JetBlue
JetBlue, American Airlines, and Major Airline are the most popular carriers operating from Chicago to Key West
What is the cheapest route?
Chicago O'Hare Intl - Key West
Fly from Chicago O'Hare Intl to Key West for the best Chicago - Key West flight prices
When is the cheapest time to book a flight to Key West?
60 days before
The cheapest time to buy a flight from Chicago to Key West is approximately 60 days to departure
60
Days before departure
0

Flight information for Chicago to Key West

Find info about flight duration, direct flights, and airports for your flight from Chicago to Key West
Fastest flight time 3h 24m The fastest flight from Chicago to Key West takes 3h 24m.
Direct flights Sa Direct flights go from Chicago to Key West on Saturday. Airline offering direct flights is American Airlines..
Airports in Key West 1 airport There is 1 airport near Key West: Key West (EYW)

Alternative routes for Chicago to Key West

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Chicago to Miami
Fastest flight time
3h 01m
Cheapest price
103 USD
Indianapolis to Miami
Fastest flight time
2h 46m
Cheapest price
180 USD
Indianapolis to Key West
Fastest flight time
4h 14m
Cheapest price
258 USD

Flights from Chicago to:

Flights to Key West from:

  • Chicago
  • Illinois
  • United States
  • North America