August is by far the best month, wherein you can get cheapest flights for Chicago to Key West. Meanwhile, is perceived as the expensive month due to the varying factors. That’s why it’s highly advised to make advanced online flight booking to save huge amounts of money.
Disclaimer - All the above-mentioned fares were found within last 48 hrs. The displayed fares are based on historical data and are subject to change. The fares cannot be guaranteed at the time of booking.
ORD
14:03
Chicago
Chicago O Hare International Airport
Fri , 21 Nov 2025
EYW
21:47
Key West
Key West International Airport
Fri, 21 Nov 2025
ORD
08:30
Chicago
Chicago O Hare International Airport
Fri , 21 Nov 2025
EYW
12:51
Key West
Key West International Airport
Fri, 21 Nov 2025
ORD
11:00
Chicago
Chicago O Hare International Airport
Fri , 21 Nov 2025
EYW
15:19
Key West
Key West International Airport
Fri, 21 Nov 2025
ORD
11:19
Chicago
Chicago O Hare International Airport
Fri , 21 Nov 2025
EYW
17:12
Key West
Key West International Airport
Fri, 21 Nov 2025
ORD
10:55
Chicago
Chicago O Hare International Airport
Thu , 14 May 2026
EYW
15:06
Key West
Key West International Airport
Thu, 14 May 2026
ORD
12:07
Chicago
Chicago O Hare International Airport
Thu , 14 May 2026
EYW
18:23
Key West
Key West International Airport
Thu, 14 May 2026
ORD
08:00
Chicago
Chicago O Hare International Airport
Thu , 14 May 2026
EYW
12:16
Key West
Key West International Airport
Thu, 14 May 2026
ORD
13:15
Chicago
Chicago O Hare International Airport
Thu , 14 May 2026
EYW
19:44
Key West
Key West International Airport
Thu, 14 May 2026
Flying from Chicago to Key West has never been easier. Whether you’re planning a short business trip, a weekend getaway, or reconnecting with family and friends, Easemytrip brings you the best deals, seamless booking, and flexible options for this popular flight route. Our platform is built to help travellers like you compare flight prices, explore direct and connecting options, and find the perfect departure time — all within a few clicks.
The air route between Chicago to Key West is one of the most frequently travelled, offering reliable services from top airlines and excellent connectivity between Chicago O Hare International Airport (ORD) and Key West International Airport (EYW). You can expect a flight distance of approximately 2018 km, and most direct services cover it in around 05:25.
Let’s take a closer look at everything you need to know before booking your flight from Chicago to Key West.
Flight Details | Information |
---|---|
Route Distance | 2018 km |
Average Flight Time | 05:25 hrs |
Departure Airport | Chicago O Hare International Airport (ORD) |
Arrival Airport | Key West International Airport (EYW) |
Cabin Classes Available | Economy Class, Premium Economy, Business Class, First Class |
Direct Flights | YES |
Common Airlines | American Airlines, United Airlines, Delta Airlines |
The route is serviced regularly by both full-service and budget airlines, catering to all types of travellers — from those looking for no-frills budget options to those preferring business and first-class comfort. If you're flying for business, early morning weekday flights are a great choice, while leisure travellers often opt for weekend and evening departures.