Cheap Flights from Chicago to Havana

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Find the cheapest month or even day of the year to fly to Havana

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Flight deals from Chicago to Havana Airport

Looking for a cheap last-minute deal or the best return flight from Chicago to Havana Airport? If you want to travel next month, return fares start from R 8,200. 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 June.

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.

Chicago to Havana: Flight information

The things to know before you go.
Cheapest flight foundR 2,792
Cheapest month to flyJune

Finding cheap flights from Chicago to Havana: Frequently asked questions

The best price we found for a return flight from Chicago to Havana is R 4,630. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Chicago to Havana. But we found flights with one stop from R 4,630.
As of March 2026, there are no flights flying from Chicago to Havana.
The cheapest month to fly from Chicago to Havana is usually May.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Havana Airport on Saturday, 30 May 2026.
No airlines currently offer direct flights between Chicago and Havana Airport. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Havana but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Havana is around 40 days in advance, so don’t leave your flight to the last minute.
The cheapest airline that flies to Havana is Viva .

Travelling from Chicago to Havana Jose Marti International Airport (HAV): What you need to know

  • Havana is one hour ahead of Chicago. Havana Jose Marti International Airport is located in Havana, which is in the UTC-5 timezone.

  • Give yourself plenty of time to get on your flight from Chicago to HAV. It's generally best to arrive at least two hours before international departures and an hour ahead for domestic flights.

  • With more travellers during peak months like July, get to the terminal earlier than usual. Two hours for domestic flights and up to four for international journeys will allow extra time for delays. Remember things also get busy during major holidays like July Fourth.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • Think about adding a stopover to find cheap flights from Chicago to HAV. Just deselect 'Direct flights only' when searching for departures from Chicago O'Hare International Airport (ORD). Break up the journey at one of these popular options:

    • Houston George Bush Intercontinental Airport (IAH)

    • Miami International Airport (MIA)

    • Cancun International Airport (CUN)

  • ORD is around 27 kilometres from central Chicago. If you're catching a taxi, ride-sharing or driving from the centre, it'll take 30 minutes or so to get there, depending on traffic. If you're taking public transport, expect the travel time to be around 45 minutes.

  • In search of a comfortable hotel close to Chicago O'Hare International Airport? If you're catching an early flight from Chicago to Havana Jose Marti International Airport, these accommodation options will put you conveniently close to check-in:

  • When it comes to the on-time performance of Chicago O'Hare International Airport, data shows 75% of flights complete their journey on time.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Add a little extra to your holiday with a stopover on your flight from Chicago to Havana Jose Marti International Airport. Check out these connections between Chicago Midway International Airport and HAV:

    • Miami International Airport (MIA)

    • Cancun International Airport (CUN)

    • Tampa International Airport (TPA)

  • On public transport, you can travel from central Chicago to MDW in around 30 minutes. The terminal is roughly 16 kilometres away, and making the trip by car takes approximately 25 minutes.

  • Get your holiday started early with an extra night away from home. Before your Chicago to HAV flight, stay in one of these hotels close to Chicago Midway International Airport:

  • When it comes to flights staying on schedule, Chicago Midway International Airport has an on-time arrival performance of 77%.

  • MDW is located at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • RFD is roughly 145 kilometres from central Chicago. The drive from the city centre to the terminal takes about 1 hour 40 minutes. If you're considering public transport, you can expect a journey of around 2 hours.

  • Set yourself up for a smooth departure — stay close to Chicago Rockford International Airport and know you'll make it to your boarding gate with time to spare. Get settled at one of these hotels the day before if you're catching an early Chicago to Havana Jose Marti International Airport flight:

  • Flights departing from RFD touch down at their destination within the expected time frame 76% of the time.

  • Chicago Rockford International Airport is located at 2 Airport Cir.

About Havana Jose Marti International Airport (HAV)

  • Consider checking in to Apartamento Familia Campa Daniela - Old Havana after touching down from your flight from Chicago to Havana Jose Marti International Airport. It's a quick drive from HAV and a good option if you'd like to relax as soon as possible.

Getting from Havana Jose Marti International Airport (HAV) to central Havana

  • From Havana Jose Marti International Airport, central Havana is around 16 kilometres away. It takes about 25 minutes to reach the city centre by car.

  • If you're using public transport, expect a journey time of roughly 1 hour.

How to find the cheapest flights from Chicago to Havana Jose Marti International Airport (HAV)

  • R 2,792 is the best price for a one-way ticket from Chicago to Havana Jose Marti International Airport. A return flight starts from R 4,630. These fares may change based on demand.

  • Booking early is often the key to finding a cheap flight from Chicago to HAV. Prices tend to rise as demand increases, so the closer you get to departure, the more you'll likely pay.

  • Affordable Chicago to Havana Jose Marti International Airport tickets are easier to find when you have flexibility in your schedule. Use the 'Whole month' tool to compare fares across each month and then fly out on the cheapest day.

  • You don't need to check every day to find out if prices have dropped when you create a Price Alert. We'll notify you as soon as there's a better deal on plane tickets from Chicago to HAV.

  • Nail down a great price on a flight from Chicago to Havana Jose Marti International Airport with the help of the filters. Pick your preferred arrival and departure times, airlines and number of stops. You can also sort your results by 'Best,' 'Fastest' or 'Cheapest.'

The best time to fly from Chicago to Havana Jose Marti International Airport (HAV)

  • Think about the kind of experience you want when deciding when to fly. September is the quietest month to go to Havana. March is when most people book flights from Chicago to Havana Jose Marti International Airport (HAV), which may be ideal if you're chasing more excitement.

  • Lock in a Chicago to HAV plane ticket departing in July if you want to experience the city during its warmest month. Expect temperatures in Havana to range from 23ºC (73ºF) to 35ºC (95ºF).

  • January has temperatures of between 17ºC (63ºF) and 28ºC (82ºF). Search for cheap tickets from Chicago to Havana Jose Marti International Airport around that time if you want to travel in cooler conditions.

More about Havana

  • Once you've booked your flight from Chicago to Havana Jose Marti International Airport, choose a hotel that puts you where you want to be. Make one of these options your base for exploring Havana:

  • Paseo del Malecón and Old Havana are just a couple of the top-rated attractions to put on your Havana must-do list. Keep the sightseeing going at La habana.

Explore more of Cuba

  • Santa Clara is just one of the many places in Cuba waiting to be discovered once you've taken in the sights of Havana. Around 257 kilometres away to the east, popular attractions include Che Guevara Mausoleum, Plaza de La Revolución Ernesto Che Guevara, Santa Clara Cuba and Abbey Road Park (The Beatles park).

  • Around 145 kilometres southwest of Havana, Pinar del Río is another essential stop in Cuba. Experience major highlights starting with Parque Nacional Peninsula de Gunanahacabibes, Martí Park and Independencia Park.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.