United Airlines
Star Alliance
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United States
Key West International Airport
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United States
O'Hare International Airport
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Scan through all non-stop flights from Key West to Chicago. The full flight schedule below gives an overview of all non-stop flights from EYW to ORD, which includes the daily timetable of every operating airline for the upcoming 12 months.
Note: for airline-specific flight schedules, please scroll further down.
Known for its continental climate, Chicago features hot, humid summers with temperatures above 30°C (86°F) and cold, snowy winters that often drop below 0°C (32°F). This striking seasonal contrast offers travelers a variety of activities, from summer hiking to winter sports, ensuring year-round appeal.
The best time to visit Chicago is from March to November, covering spring, summer, and fall. While summer can be hot, it also sees slightly more rainfall than other seasons.
In total there are 2 airlines operating nonstop flights from Key West EYW to Chicago ORD. This section gives an overview of the flight schedules and timetables of every airline with direct flights for this route.
Click an airline below to view their EYW ORD flight schedule.
Flights from EYW to ORD are operated 19 times a week, with an average of 3 flights per day. Departure times vary between 07:00 - 18:49. The earliest flight departs at 07:00, the last flight departs at 18:49. However, this depends on the date you are flying so please check with the full flight schedule above to see which departure times are available on your preferred date(s) of travel.
You can fly in Economy and Business Class. Premium Economy and First Class are not available on this route (at least not as a non-stop flight).
The fastest direct flight from Key West to Chicago takes 3 hours and 33 minutes. The flight distance between Key West and Chicago is 1,253 miles (or 2,017 km).
There are 2 airports in Chicago: O'Hare International Airport (ORD) and Midway International Airport (MDW).
There are 19 flights per week flying from Key West to Chicago (as of April 2026).
3 hours and 33 minutes is the average flight time from Key West to Chicago.
The distance from Key West to Chicago is 1,253 miles (2,017 kilometers).
American Airlines and United Airlines are flying nonstop from Key West to Chicago.
Oneworld and Star Alliance are flying nonstop from Key West to Chicago.
You can fly non-stop in Economy and Business Class.
Aircraft types that fly from Key West to Chicago:
The earliest flight departs at 07:00 from Key West and arrives at 09:25 at Chicago.
The latest flight departs at 18:49 from Key West and arrives at 21:38 at Chicago.
1,253 miles (2,017 km) · 3h 33m
12:05
15:00
United Airlines
Star Alliance
UA 3578
United Airlines
Embraer 175
Y
W
J
F
13:08
15:55
American Airlines
Oneworld
AA 3582
American Airlines
Embraer 170
Y
W
J
F
13:08
15:55
American Airlines
Oneworld
AA 3582
American Airlines
Embraer 170
Y
W
J
F
15:52
18:36
United Airlines
Star Alliance
UA 2304
United Airlines
Boeing 737-700
Y
W
J
F
15:52
18:36
United Airlines
Star Alliance
UA 2304
United Airlines
Boeing 737-700
Y
W
J
F
16:05
19:00
United Airlines
Star Alliance
UA 3532
United Airlines
Embraer 175
Y
W
J
F
18:46
21:35
American Airlines
Oneworld
AA 3960
American Airlines
Embraer 170
Y
W
J
F
18:49
21:38
American Airlines
Oneworld
AA 3960
American Airlines
Embraer 170
Y
W
J
F
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