starting at $249
Compare airlines, prices, and flight durations for your trip
A non-stop flight is the most convenient and comfortable way to fly from Havana to Chicago, despite the fact that sometimes flights with transfers can cost significantly less.
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Havana to Chicago:
•
•
•
•
•
•
We keep tight track on airlines' pre-holidays sales and other special offers occurences all the time to let you save maximum amount of funds while traveling to your family or just going out on vacation.
Looking for cheap flights from Havana, Cuba to Chicago, United States? Look no further! Our air ticket search website is here to help you find the best deals and save money on your travel expenses. With our user-friendly interface, you can easily compare prices from various airlines and choose the most affordable option that suits your budget. Whether you're planning a vacation or a business trip, we've got you covered. Discover the vibrant city of Chicago, renowned for its iconic architecture, world-class museums, and vibrant food scene. Don't miss out on exploring the Magnificent Mile, Millennium Park, and Navy Pier. Start your journey today by booking your flights from Havana to Chicago with us and enjoy a seamless travel experience without breaking the bank.
The route Havana — Chicago is served by a single airline — Southwest Airlines. This means that when planning your trip, you won’t need to spend time choosing between dozens of carriers: all flights are operated by one provider, which simplifies the booking process. Despite the limited choice, passengers can still plan ahead, select optimal departure dates, and buy tickets at the lowest price — from $249. Using our service, you can quickly compare available Southwest Airlines flights and book a seat in advance at a favorable rate.
starting at $249
There appear to be no non-stop flights from Havana to Chicago at this time.... Well, or something went wrong on our side and we couldn't find anything
Unable to find information about the schedule of direct flights from
The cheapest one-way flight from Havana to Chicago departs on 05/06/2026, is operated by Southwest Airlines and costs $249
There is no information about the cheapest roundtrip flight from Havana to Chicago
Fastest flight from Havana to Chicago takes 7h 50m
There are no direct flights on this route.
The distance between Havana and Chicago is 2154km (1335 miles). The time difference between Havana and Chicago is 1h
We couldn't find any special offers for flights from Havana to Chicago
The cheapest flight ticket from Havana to Chicago according to data for the last 48 hours costs $249
Often the best time to buy tickets from Havana to Chicago is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Havana to Chicago can be found flying in these months: May.
The fastest flights from Havana to Chicago start from 7 hours 50 minutes in the air.
The following airlines operate direct flights on the route Havana — Chicago:
We carefully collect statistics on the search and pricing of airlines and, based on these data, we make an assumption about future prices. Thus, you can better understand which season is the cheapest to fly from Havana to Chicago