Airports with direct flights to 30+ destinations
Airports with direct flights to 7 to 30 destinations
Airports with direct flights to less then 7 destinations
Show flights within a certain date range
Show flights within a certain price range
Show flights operated by a specific alliance
Show flights operated by a specific airline
Show flights in a specific flight class
Show flights operated by a specific aircraft
Show direct flights, or flights with 1 or 2 stopovers
Show connecting flights with the same airline only
Where would you like to fly from?
Where would you like to fly to?
Did you mean flights from Chicago to Key West?
United States
Key West International Airport
Switch direction
United States
Midway International Airport
At present, there are no direct flights from Key West to Chicago.
However, there are several flights from EYW to MDW with a stopover.
Select a stopover airport from the list below to see which airlines operate flights from EYW to MDW, and to see what flight schedules are available.
In total there are 2 airlines that cover the full route from Key West EYW to Chicago MDW. These airlines are:
All other flights from Key West to Chicago are operated by a combination of multiple carriers, which are listed below:
SkyTeam is the only alliance that covers the full route (with 1 stopover) from Key West EYW to Chicago MDW.
You can fly the full journey from EYW to MDW in either Economy or Business Class. Premium Economy and First Class are not available on this route, at least not on the full route with just 1 stopover.
At this moment, it is not possible to cover the full route from Key West to Chicago (with 1 stopover) with one specific type of aircraft. All flights from Key West to Chicago are operated by a combination of multiple aircraft types.
The distance between Key West and Chicago is 1,240 miles (1,996 kilometers).
However, because there are no direct flights between EYW and MDW, the distance of the full journey varies between 1,264 and 2,232 miles (or 2,034 and 3,592 kilometers), depending on your stopover airport.
Flights from Key West to Chicago take from 3 hours and 48 minutes up to 6 hours and 4 minutes, depending on your stopover airport.
Please note that these times refer to the actual flight times, excluding the stopover time in between connecting flights, as this depends on your stopover airport as well as your date(s) of travel.
There are 2 airports in Chicago: Midway International Airport (MDW) and O'Hare International Airport (formerly Orchard Depot Fi (ORD).
From 3 hours and 48 minutes up to 6 hours and 4 minutes, depending on your stopover airport.
Note that this excludes the layover time in between connecting flights.
Because there are no direct flights between EYW and MDW, the total distance of the full journey varies between 1,264 and 2,232 miles (or 2,034 and 3,592 kilometers), depending on your stopover airport.
Allegiant and Delta are flying the full route from Key West to Chicago.
Southwest Airlines, Frontier Airlines, Silver Airways, American Airlines and JetBlue operate several connecting flights, but only partly.
SkyTeam is currently the only alliance flying from Key West to Chicago.
You can fly the full route from Key West to Chicago (with 1 stopover) in Economy and Business Class.
There is no specific aircraft type that covers the full route (with 1 stopover) from Key West to Chicago at this moment.
This website is made possible by displaying online advertisements to our visitors.
Please support us by disabling your ad blocker. Or choose one of our plans.
Stay informed ↓