$652 Cheap Flights from Chicago to Havana in 2025

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

Havana.$652 per passenger.Departing Thu, 8 May, returning Mon, 12 May.Return flight with Copa.Outbound indirect flight with Copa, departs from Chicago O'Hare International on Thu, 8 May, arriving in Havana.Inbound indirect flight with Copa, departs from Havana on Mon, 12 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From $652, select.

Havana.$720 per passenger.Departing Mon, 6 Oct, returning Sun, 12 Oct.Return flight with Copa.Outbound indirect flight with Copa, departs from Chicago O'Hare International on Mon, 6 Oct, arriving in Havana.Inbound indirect flight with Copa, departs from Havana on Sun, 12 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From $720, select.

Havana.$723 per passenger.Departing Wed, 4 Jun, returning Sat, 7 Jun.Return flight with Copa.Outbound indirect flight with Copa, departs from Chicago O'Hare International on Wed, 4 Jun, arriving in Havana.Inbound indirect flight with Copa, departs from Havana on Sat, 7 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From $723, select.

Havana.$723 per passenger.Departing Thu, 18 Sep, returning Mon, 22 Sep.Return flight with Copa.Outbound indirect flight with Copa, departs from Chicago O'Hare International on Thu, 18 Sep, arriving in Havana.Inbound indirect flight with Copa, departs from Havana on Mon, 22 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From $723, select.

Havana.$765 per passenger.Departing Wed, 30 Apr, returning Sat, 3 May.Return flight with Copa.Outbound indirect flight with Copa, departs from Chicago O'Hare International on Wed, 30 Apr, arriving in Havana.Inbound indirect flight with Copa, departs from Havana on Sat, 3 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From $765, select.

Havana.$776 per passenger.Departing Tue, 20 May, returning Sat, 7 Jun.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 20 May, arriving in Havana.Inbound indirect flight with Southwest Airlines, departs from Havana on Sat, 7 Jun, arriving in Chicago Midway.Price includes taxes and charges.From $776, select.

Havana.$796 per passenger.Departing Fri, 18 Apr, returning Mon, 21 Apr.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Fri, 18 Apr, arriving in Havana.Inbound indirect flight with United, departs from Havana on Mon, 21 Apr, arriving in Chicago O'Hare International.Price includes taxes and charges.From $796, select.

Havana.$796 per passenger.Departing Fri, 13 Jun, returning Fri, 18 Jul.Return flight with Copa.Outbound indirect flight with Copa, departs from Chicago O'Hare International on Fri, 13 Jun, arriving in Havana.Inbound indirect flight with Copa, departs from Havana on Fri, 18 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From $796, 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 May.

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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.

Chicago to Havana: Flight information

The things to know before you go.

Cheapest flight found	$652
Cheapest month to fly	May

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 $652. 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 $652.

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

As of March 2025, 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 March 2025.

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 Thursday, 8 May 2025.

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 Copa .

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

Start your travel planning by considering where you'll take off for your flight from Chicago to Jose Marti International Airport (HAV). O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) are the main airports in Chicago.
Havana is 1 hour ahead of Chicago. Jose Marti International Airport is located in Havana, which operates on the UTC-4 timezone.
Your flight from Chicago to HAV won't wait if you're running late, so show up at the airport on time. Arrive up to one hour in advance for domestic flights and two hours ahead when you're travelling internationally.
Hopping on a plane during a peak time like August? Busy periods (like summer, Thanksgiving, Christmas and spring break) can add another hour at check-in and security. Be extra cautious and arrive up to four hours ahead of an international flight and two hours before domestic departures.

Airports in Chicago

O'Hare International Airport (ORD)

Think about adding a stopover to potentially save on your flight from Chicago to HAV. Simply deselect 'Direct flights only' when searching for departures from O'Hare International Airport (ORD). Break up your trip (and maybe save some cash) by stopping at one of these airports:
- Cancun International Airport (CUN)
- Tampa International Airport (TPA)
- Miami International Airport (MIA)
ORD is about 40 kilometres from central Chicago. To work out how to get there, use Google Maps. This handy traveller tool will show you the best route and available public transport options.
Want a convenient hotel close to O'Hare International Airport? If you're boarding an early flight from Chicago to Jose Marti International Airport, these stays will have you sleeping moments from your departure gate:

Chicago Midway International Airport (MDW)

Split up your flight from Chicago to Jose Marti International Airport with a stop so you can stretch your legs or perhaps go somewhere you've never been before. Some great stopovers between Chicago Midway International Airport and HAV include:
- Tampa International Airport (TPA)
- Miami International Airport (MIA)
- Cancun International Airport (CUN)
MDW is around 19 kilometres from central Chicago. It takes 21 minutes or so to get to the airport in a car from the city centre. Public transport takes approximately 46 minutes.
It's your holiday, so why not enjoy another night away? Consider kicking back in one of these hotels near Chicago Midway International Airport the day before your flight from Chicago to HAV:

About Jose Marti International Airport (HAV)

If you have a late flight from Chicago to Jose Marti International Airport, nothing tops the convenience of staying close to the terminal. Collect your bags from the carousel and then be showered and relaxing not long after at one of these hotels near HAV:

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

From Jose Marti International Airport, Havana is approximately 16 kilometres away. It takes around 30 minutes to get to the centre driving.

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

The best price we've found for a one-way ticket from Chicago to Jose Marti International Airport is $357. The cheapest price for a return flight is $652. Keep in mind fares can change due to availability at the time of booking.
It's usually smart to book as early as possible if you want to find flight tickets from Chicago to HAV. That's because flight prices are based on demand, which tends to rise closer to the date of departure.
Use the 'Whole month' search function to compare the prices of tickets from Chicago to Jose Marti International Airport across each month. We've made the lowest fares green, so you can quickly pick a flight that fits your budget.
Create a Price Alert and track any changes on this route through email or push notifications. You'll know straight away when fares go down. It's all about timing when scoring flight tickets from Chicago to HAV.
Make the most of the filters to find your ideal trip. To see the 'Cheapest,' 'Best' or 'Fastest' flights from Chicago to Jose Marti International Airport, use the 'Sort by' function. You can also filter results by airline, arrival and departure times, and journey duration.

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

April is the quietest time of year to travel to Havana. Alternatively, join the crowds and get away in August. This is the busiest month for flights from Chicago to Jose Marti International Airport.
The warmest month in Havana is July, with the temperature ranging between 23ºC and 35ºC. Book your flights from Chicago to HAV in this month if this is the type of weather you enjoy.
January sees average temperatures of between 17ºC and 28ºC. Look for cheap flights from Chicago to Jose Marti International Airport around that time if you'd rather travel in cooler conditions.

More about Havana

Start your Havana trip right by choosing the ideal place to stay. After booking your flight from Chicago to Jose Marti International Airport, browse our selection of accommodation options including:
One of the best ways to experience Havana is to check out its leading attractions. Highlights include Old Havana, Malecon and Museo Nacional de Bellas Artes.

Complete your Havana trip with a car rental

Finding you a cheap flight from Chicago to Jose Marti International Airport isn't the only thing we're good at. Check out our car rentals in Havana and explore the city on your own terms. We find deals from trusted car rental companies and put them all in one place. Instantly compare rates and then book with no fees.