How to find cheap flights from Chicago Midway Airport (MDW) to Cuba
Book a return flight from Chicago Midway Airport (MDW) to Cuba starting at Rs129,771, the cheapest price currently available.
That fare will get you from MDW into Havana in Havana.
Rs76,441 is the lowest price we've found for a one-way ticket.
Want to let the lowest fares decide your next stop? Select 'Cuba' in the 'To' field to find the cheapest deals by city.
Cuba has around five international airports, so you'll have no shortage of arrival options.
Select 'Add nearby airports' to broaden your search and compare prices across all airports close to both your origin and destination cities.
Aim to book around one month before your departure date to find a lower fare. You might want to book even earlier if you're flying when it's busy.
Know as soon as fares change. Download the Skyscanner app, set up a Price Alert, and we'll send you updates when prices go up or down.
Best time to fly from Chicago Midway Airport (MDW) to Cuba
Hop on a flight from Chicago Midway Airport (MDW) to Cuba in December and you'll be travelling at one of the cheapest times of the year. Prices start at Rs129,771.
In general, a midweek flight is a simple way to save. Tuesdays and Wednesdays often mean lower prices.
The busiest months to fly to Cuba are January, February and March. March is the most popular month, which can bring higher fares.
July, August and September are the least popular months to fly. The quietest month is September. Fewer people are booking seats, so airlines tend to drop prices to help fill flights.
Popular places to visit in Cuba
Once you've secured your Chicago to Cuba flights, it's time to plan your trip.
Havana
Located in La Habana Province, this city is one of the most popular destinations for flights departing Chicago Midway Airport and heading to Cuba. Start your sightseeing at main attractions like Old Havana, Malecón of Havana and Faro Castillo del Morro.
Havana Jose Marti International Airport (HAV) manages most international flights into Havana.
Check out the lineup of hotels in Havana and pair your trip with a stay you'll love.
Varadero
Playa Varadero, Varadero and Varadero Beach, Cuba offer a solid introduction to the highlights in this Matanzas Province city.
Varadero Juan Gualberto Gomez Intl Airport (VRA) is the city's main airport.
After your plane ticket is locked in, you can focus on finding the right stay among the hotels in Varadero.
Santiago
Swing by major sights like Bacardi Rum Factory, Moncada Barracks and Sierra Maestra while you're in this corner of Santiago de Cuba Province.
Santiago de Cuba Antonio Maceo Intl Airport (SCU) is the city's main airport, with routes linking it to popular destinations across the region and beyond.
Whether you prefer fuss-free comfort or something fancier, hotels in Santiago offer options for every kind of trip.
Visiting Cuba for the first time? Here's what you need to know
Entry rules can vary, so it's worth checking whether you'll need a visa or other documents before you travel. Your airline, travel agent or the local consulate or embassy will have the most up-to-date information.
You'll be using Cuban peso (CUP) for all your purchases.
Cuba has a population of about 9.7 million. The capital city is Havana.
You won't need to adjust your watch while travelling through this destination, with only one standard time zone of UTC-5 inches place.
The weather can shape everything from what you wear to what you see, so travel when the forecast suits your plans. August is Cuba's warmest month, with average daytime highs reaching 32ºC.
Temperatures are often coolest around January, when average low temperatures drop to 20ºC. Check the weather before travelling.
March tends to be the driest month, while May is the wettest.
Headline events on the local calendar include Santiago de Cuba Carnival, the Havana International Jazz Festival and Remedios Parrandas Festival. Time your getaway around occasions like these to experience something beyond the everyday.
Complete your trip with hotels and a car rental
With your cheap flight from Chicago Midway Airport (MDW) to Cuba locked in, it's now time to plan the rest of your travels. Find competitive prices and exclusive rates for hotels in Cuba. You can also browse the car rental options and compare deals from leading suppliers in seconds.
