How to find cheap flights from Chicago to Cuba
R 7,566 is currently the cheapest price for a return flight from Chicago to Cuba.
You'll be travelling from Chicago into Havana in Havana with that fare.
A one-way ticket starts at R 3,657.
Need some ideas on where to fly to? Enter 'Cuba' in the 'To' field to compare fares to different cities.
There's no shortage of ways to arrive in Cuba, with roughly five airports to choose from.
To compare a wider range of prices, select 'Add nearby airports' to include all airports close to where you're departing from and heading to.
The earlier you book, the better. Fares are more likely to go up as your departure date gets closer, not fall.
Easily track fare changes by setting up a Price Alert. If you haven't already, download the Skyscanner app to get instant updates.
Best time to fly from Chicago to Cuba
November is usually the cheapest month to catch a flight from Chicago to Cuba.
Midweek travel can often be a smarter choice. Prices are generally cheaper on Tuesdays and Wednesdays than at the weekend.
February, March and August are the busiest months to travel to Cuba. February leads the way, making it a great time to visit if you want to see the place buzzing.
Alternatively, avoid the peak season surge by searching for flights in April, September and October. Out of these low season months, April is the quietest.
Popular places to visit in Cuba
Havana
A popular destination for Chicago to Cuba flights, this city in La Habana Province takes the top spot on the must-visit list. From Old Havana and Malecón de Habana to Malecón of Havana, the attractions just keep coming.
Havana Airport (HAV) is Havana's main airport.
When you're ready to find somewhere comfortable to stay, browse the selection of hotels in Havana.
Varadero
Big-name draws in this Matanzas Province city include Playa Varadero, Varadero and Varadero Beach, Cuba.
Varadero Airport (VRA) is the city's main airport.
With your airfare locked in, you can focus on finding the right stay among the hotels in Varadero.
Holguin
Drop by popular sights like Hill of the Cross (Loma de la Cruz), Bahia de Naranjo Nature Park and Natural History Museum (Museo de Historia Natural) while you're in this corner of Holguín Province.
Holguin Airport (HOG) is the main airport for flights into the city.
Find a deal on where you'll stay by exploring the list of hotels in Holguin.
Visiting Cuba for the first time? Here's what you need to know
Entry rules can vary, so check whether you'll need a visa or any other type of documentation before you travel. Your travel agent, airline or the local embassy or consulate will have the most up-to-date information.
The main currency is the Cuban peso (CUP).
Cuba has a population of roughly 9.7 million. The capital city is Havana.
The same time is used throughout this destination, with only one standard time zone operating on UTC-5.
Pick the season that matches how you like to travel, whether that's cooler, hotter or somewhere in between. August is one of the warmest months in Cuba.
Plan your trip for sometime around January if you prefer cooler conditions.
Rain is more frequent in September, while January is typically drier.
Want to time your Chicago to Cuba flight with a big occasion? Popular events to build your trip around include Santiago de Cuba Carnival, the Havana International Jazz Festival and Remedios Parrandas Festival.
Complete your trip with hotels and a car rental
With your cheap flight from Chicago to Cuba locked in, it's time to plan the rest of your travels. Discover competitive prices and places to suit every budget across hotels in Cuba. You can also browse car rental options in Cuba and compare deals from trusted companies in seconds.
