268 € Chicago (CHIA) to Havana (HAV) Cheap Flights

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Flight deals from Chicago to Havana

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 438 €. Find the lowest prices on one-way and return tickets right here.

Havana.268 € per passenger.Departing Sat, 15 Aug, returning Sat, 29 Aug.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Sat, 15 Aug, arriving in Havana.Inbound indirect flight with Viva, departs from Havana on Sat, 29 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From 268 €, select.

Havana.279 € per passenger.Departing Fri, 28 Aug, returning Sat, 5 Sep.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Fri, 28 Aug, arriving in Havana.Inbound indirect flight with Viva, departs from Havana on Sat, 5 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From 279 €, select.

Havana.412 € per passenger.Departing Mon, 29 Jun, returning Tue, 7 Jul.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 29 Jun, arriving in Havana.Inbound indirect flight with Southwest Airlines, departs from Havana on Tue, 7 Jul, arriving in Chicago Midway.Price includes taxes and charges.From 412 €, select.

Havana.438 € per passenger.Departing Mon, 6 Jul, returning Tue, 14 Jul.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 6 Jul, arriving in Havana.Inbound indirect flight with Southwest Airlines, departs from Havana on Tue, 14 Jul, arriving in Chicago Midway.Price includes taxes and charges.From 438 €, select.

Havana.448 € per passenger.Departing Sat, 25 Jul, returning Sat, 1 Aug.Return flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Sat, 25 Jul, arriving in Havana.Inbound indirect flight with Viva, departs from Havana on Sat, 1 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From 448 €, select.

Havana.455 € per passenger.Departing Thu, 5 Nov, returning Tue, 10 Nov.Return flight with Copa.Outbound indirect flight with Copa, departs from Chicago O'Hare International on Thu, 5 Nov, arriving in Havana.Inbound indirect flight with Copa, departs from Havana on Tue, 10 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From 455 €, select.

Havana.455 € per passenger.Departing Wed, 9 Sep, returning Sun, 27 Sep.Return flight with Copa.Outbound indirect flight with Copa, departs from Chicago O'Hare International on Wed, 9 Sep, arriving in Havana.Inbound indirect flight with Copa, departs from Havana on Sun, 27 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From 455 €, select.

Havana.476 € per passenger.Departing Tue, 23 Jun, returning Tue, 30 Jun.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 23 Jun, arriving in Havana.Inbound indirect flight with Southwest Airlines, departs from Havana on Tue, 30 Jun, arriving in Chicago Midway.Price includes taxes and charges.From 476 €, select.

Havana.933 € per passenger.Departing Sun, 13 Dec, returning Sat, 2 Jan.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 13 Dec, arriving in Havana.Inbound indirect flight with Southwest Airlines, departs from Havana on Sat, 2 Jan, arriving in Chicago Midway.Price includes taxes and charges.From 933 €, select.

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 August.

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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.

Havana

18km from central Havana

ClosestCheapest

from 268 €

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Playa Baracoa

26km from central Havana

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Chicago to Havana: Flight information

The things to know before you go.

Cheapest flight found	268 €
Cheapest month to fly	August

Finding cheap flights from Chicago to Havana: Frequently asked questions

How much are return flights from Chicago to Havana?

The best price we found for a return flight from Chicago to Havana is 268 €. 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.

Which airlines fly direct from Chicago to Havana?

Currently, there are no airlines that fly direct from Chicago to Havana. But we found flights with one stop from 268 €.

How many flights are there a week from Chicago to Havana?

As of June 2026, there are no flights flying from Chicago to Havana.

When is the cheapest time to fly from Chicago to Havana?

The cheapest month to fly from Chicago to Havana is usually August.

Which upcoming date is cheapest to fly from Chicago to Havana Airport on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Havana Airport on Saturday, 15 August 2026.

Can I get a direct flight from Chicago to Havana Airport?

No airlines currently offer direct flights between Chicago and Havana Airport. Most routes have one or more stops.

How can I find the best flight deal to Havana?

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.

When is the best time to book flights to Havana?

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.

Which is the cheapest airline to fly from Chicago to Havana with?

The cheapest airline that flies to Havana is Viva .

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

The timezone in Havana is UTC-5, which is one hour ahead of Chicago. Havana Jose Marti International Airport is located in Havana.
For hassle-free travel, turn up at the airport two hours ahead of international flights and one hour before domestic departures. This ensures you have enough time to board your flight from Chicago to HAV.
July is a busy time to fly out. If you're heading away then or around a major holiday like Thanksgiving, Memorial Day or Christmas, get there even earlier. Aim for at least two hours ahead for domestic flights and up to four hours for international journeys.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

We make it a breeze to find cheap flights from Chicago to HAV that include a stopover. To explore all your options leaving from Chicago O'Hare International Airport (ORD), uncheck 'Direct flights only.' Then, simply choose a flight with a stop long enough to tour the city of your choice. Some popular stopovers between ORD and HAV include:
- Houston George Bush Intercontinental Airport (IAH)
- Miami International Airport (MIA)
- Cancun International Airport (CUN)
The journey from central Chicago to ORD takes around 45 minutes on public transport. If you ride-share, drive or grab a taxi, you'll cover the 27 kilometres in 30 minutes or so, depending on traffic.
Booked an early flight from Chicago to Havana Jose Marti International Airport? Avoid rushing to the terminal (and get some bonus sleep) by picking one of these stays close to Chicago O'Hare International Airport:
70% of flights that leave from Chicago O'Hare International Airport touch down at their destination on schedule.
The address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

Knock a new city off your list or just take a moment to recharge with a stopover. If you'd like to split up your flight from Chicago to Havana Jose Marti International Airport, check out these options when taking off from Chicago Midway International Airport:
- Miami International Airport (MIA)
- Cancun International Airport (CUN)
- Tampa International Airport (TPA)
With public transport, you can travel from central Chicago to MDW in around 30 minutes. The airport is roughly 16 kilometres away, and getting there by car takes approximately 25 minutes.
Want to enjoy an extra night away before your Chicago to HAV flight? Unwind in a hotel near Chicago Midway International Airport before your holiday officially begins. These stays have a room with your name on it:
Chicago Midway International Airport has an on-time performance rate of 76%. This figure reflects how frequently flights that leave from this airport arrive on time.
You'll find MDW at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

The trip to RFD from the centre of Chicago is around 2 hours on public transport. If you're planning to travel by car, it'll take you roughly 1 hour 40 minutes to cover the 145 kilometres or so.
Set yourself up for a smooth departure — stay close to Chicago Rockford International Airport and know you'll get to your boarding gate with time to spare. Check in to one of these hotels the day before if you've booked an early Chicago to Havana Jose Marti International Airport flight:
Airports have an on-time performance rating that monitors how often flights get to their destinations when they should. At RFD, that rate is 71%.
You'll find Chicago Rockford International Airport at 2 Airport Cir.

About Havana Jose Marti International Airport (HAV)

Consider checking in to Apartamento Familia Campa Daniela - Old Havana after your flight from Chicago to Havana Jose Marti International Airport. It's a quick drive from HAV and a great option if you want to get some rest right away.

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

Central Havana is around 16 kilometres from Havana Jose Marti International Airport and takes about 25 minutes to reach by car. Look into how to get from the airport to the city, whether that's with a taxi, car hire or ride-share.
It typically takes 1 hour if you're travelling on public transport.

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

The lowest price we've found for a one-way ticket from Chicago to Havana Jose Marti International Airport is 164 €. For a return flight on this route, the best price is 268 €. Depending on the availability and when you book, these fares can change.
Booking ahead of time is often the key to scoring a cheap flight from Chicago to HAV. Airlines adjust prices based on demand, so the closer your departure date, the more expensive your ticket may be.
The 'Whole month' search tool will show you the cheapest Chicago to Havana Jose Marti International Airport tickets across the entire month. It's a good way to snap up a bargain if your travel plans aren't set in stone.
Locking in a cheap plane ticket from Chicago to HAV couldn't be easier with Price Alerts. All you need to do is set up one of these automatic alerts and we'll get in touch as soon as prices go down.
Filters make it easier to find a bargain for your flight from Chicago to Havana Jose Marti International Airport. Choose the departure times, carriers and stops that look good to you. Then sort the results by 'Cheapest' to find the most affordable option fast.

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

July is the busiest month for flights from Chicago to Havana Jose Marti International Airport (HAV). Visit Havana in November if you'd rather be there when it's quieter.
Book a Chicago to HAV plane ticket departing in July if you're eager to explore the city during its warmest month. Expect temperatures in Havana to range from 23ºC (73ºF) to 35ºC (95ºF).
January sees 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 like cooler conditions.

More about Havana

Start your Havana trip right by choosing the perfect place to stay. After booking your flight from Chicago to Havana Jose Marti International Airport, explore our selection of accommodation options including:
There are loads of awesome things to do in Havana when you're in the mood to sightsee. Start exploring at Paseo del Malecón followed by Old Havana and La habana.

Explore more of Cuba

Santa Clara is just one of the many places in Cuba waiting to be explored once you've seen 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).
Pinar del Río is another sought-after destination in Cuba and is around 145 kilometres southwest of Havana. No trip is complete without visiting Parque Nacional Peninsula de Gunanahacabibes, Provincial Museum Of Pinar Del Rio and PALACIO DE GUASCH.