Cheap Flights from Chicago to Havana
Compare Chicago to Havana flight deals
Find the cheapest month or even day of the year to fly to Havana
Book the best Havana fare with no extra fees
Flight deals from Chicago to Havana
Looking for a cheap last-minute deal or the best return flight from Chicago to Havana? Find the lowest prices on one-way and return tickets right here.Find the cheapest month to fly from Chicago to Havana
We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Havana flights are currently cheapest in January.Oct
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Chicago to Havana: Alternative routes
Compare routes from Chicago to Havana below. You may find an airport to fly into that's cheaper, faster, or easier than Havana.Finding cheap flights from Chicago to Havana: Frequently asked questions
How to find cheap flights to Havana from Chicago
Looking for cheap tickets from Chicago to Havana? Here are a few tips on how to secure the best flight price and make your journey as smooth as possible.
- Simply hit 'search'. From British Airways to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets from Chicago to Havana. And with us there are no hidden fees - what you see is what you pay.
- Compare flight deals to Havana from Chicago from over 1,000 providers. Then choose the cheapest or fastest plane tickets.
- Flex your dates to find the best Chicago-Havana ticket prices. If you are flexible when it comes to your travel dates, use Skyscanner's 'Whole month' tool to find the cheapest month, and even day to fly to Havana from Chicago.
- Set up a Price Alert. You can easily track the fare of your cheap Chicago-Havana flights by creating an alert. Whenever prices go down or up, you'll get an email or push notification to help make sure you get the best possible flight deal.
- Fly without stops. Only interested in direct flights between Chicago and Havana? Make sure to tick 'Direct flights only' when performing a search. If there are direct flights available on the route, these will appear in the results.
- Find the cheapest Business class flights from Chicago and Havana. We scour the internet for the best Business, Premium Economy and First Class flight fares to Havana, too. Check the difference in price as you search – you might just chance upon a last-minute low fare. Note that not all cabin classes are available for every destination or airline.
- Include nearby airports in your search. Widen your search for Chicago to Havana flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save next time you travel.
Combine your flight to Havana from Chicago with hotels and car hire
Once you've secured your cheap flight ticket from Chicago to Havana, discover the best prices and exclusive rates for hotels in Havana or nearby. You can also compare hundreds of car hire companies in one go so that you get the best car hire price for your trip.
Plan the rest of your trip from Chicago to Havana
Prices shown on this page are estimated lowest prices only. Found in the last 45 days.