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 Havana to Chicago?
United States
Midway International Airport
Switch direction
Cuba
José Martí International Airport
At present, there are no direct flights from Chicago to Havana.
However, there are several flights from MDW to HAV with a stopover.
Select a stopover airport from the list below to see which airlines operate flights from MDW to HAV, and to see what flight schedules are available.
Currently, there is only one airline that covers the full route (with 1 stopover) from Chicago MDW to Havana HAV, which is Southwest Airlines.
All other flights from Chicago to Havana are operated by a combination of multiple carriers, which are listed below:
Unfortunately, there are no alliances that cover the full route (with 1 stopover) from Chicago MDW to Havana HAV at this moment.
You can fly the full journey from MDW to HAV in First Class only.
For the first part of this route, flights in Economy are available only.
Again depending on your stopover airport, available classes for the second part of this route are Economy, Premium Economy and Business Class.
Currently, there is only one aircraft type that covers the full route (with 1 stopover) from Chicago to Havana, which is the Boeing 737 MAX 8.
All other flights from Chicago to Havana are operated by a combination of multiple aircraft types.
The distance between Chicago and Havana is 1,336 miles (2,151 kilometers).
However, because there are no direct flights between MDW and HAV, the distance of the full journey varies between 1,342 and 1,851 miles (or 2,160 and 2,979 kilometers), depending on your stopover airport.
Flights from Chicago to Havana take from 4 hours and 7 minutes up to 5 hours and 23 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 is 1 airport in Havana: José Martí International Airport (HAV).
From 4 hours and 7 minutes up to 5 hours and 23 minutes, depending on your stopover airport.
Note that this excludes the layover time in between connecting flights.
Because there are no direct flights between MDW and HAV, the total distance of the full journey varies between 1,342 and 1,851 miles (or 2,160 and 2,979 kilometers), depending on your stopover airport.
Southwest Airlines is the only airline flying the full route from Chicago to Havana.
Frontier Airlines, Delta, American Airlines, VivaAerobus, Neos, Euroairlines and United Airlines operate several connecting flights, but only partly.
There are no alliances flying from Chicago to Havana at this moment.
You can fly the full route (with 1 stopover) in Economy only.
Aircraft types that fly the full route from Chicago to Havana (with 1 stopover):
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 ↓