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Flight tickets from Chicago to Havana

Your route at a glance

Cheapest deal₹ 29,363
Cheapest monthJanuary
Most popular airlineAmerican Airlines

Compare Chicago to Havana flight deals

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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.₹ 17,067 per passenger.Departing Sat, 24 Jan.One-way flight with Viva.Outbound indirect flight with Viva, departs from Chicago O'Hare International on Sat, 24 Jan, arriving in Havana.Price includes taxes and charges.From ₹ 17,067, select.
Havana.₹ 19,892 per passenger.Departing Wed, 13 May.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 13 May, arriving in Havana.Price includes taxes and charges.From ₹ 19,892, select.
Havana.₹ 21,213 per passenger.Departing Tue, 10 Mar.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 10 Mar, arriving in Havana.Price includes taxes and charges.From ₹ 21,213, select.
Havana.₹ 27,940 per passenger.Departing Mon, 1 Dec.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Mon, 1 Dec, arriving in Havana.Price includes taxes and charges.From ₹ 27,940, select.
Havana.₹ 27,978 per passenger.Departing Sat, 29 Nov.One-way flight with American Airlines.Outbound indirect flight with American Airlines, departs from Chicago O'Hare International on Sat, 29 Nov, arriving in Havana.Price includes taxes and charges.From ₹ 27,978, 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 January.
Nov
from ₹ 27,978
Dec
from ₹ 27,940
Jan
from ₹ 17,067
Feb
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Mar
from ₹ 21,213
Apr
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May
from ₹ 19,892
Jun
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Jul
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Aug
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Sep
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Oct
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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.

Finding cheap flights from Chicago to Havana: Frequently asked questions

The best price we found for a return flight from Chicago to Havana is ₹ 29,363. 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 ₹ 29,363.
As of November 2025, there are no flights flying from Chicago to Havana.
The cheapest month to fly from Chicago to Havana is usually January.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Havana Airport on Saturday, 24 January 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 .

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

  • There are a couple of airports you can start your journey from in Chicago. Explore your options leaving from O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW) when planning your flight from Chicago to Jose Marti International Airport (HAV).

  • Havana is one hour ahead of Chicago. Jose Marti International Airport is located in Havana, which is in the UTC-4 timezone.

  • To ensure you get on your flight from Chicago to HAV, leave plenty of time for things like baggage drop and finding your gate. Arriving two hours before international departures and an hour before domestic flights is the general travel rule.

  • Heading away during a peak time like school or public holidays? Expect longer queues at check-in and security. Give yourself extra leeway and arrive up to four hours before international flights and two hours before domestic departures.

Airports in Chicago

O'Hare International Airport (ORD)

  • We make it simple to book cheap flights from Chicago to HAV that include a stopover. To explore your options departing from O'Hare International Airport (ORD), uncheck 'Direct flights only.' Next, choose a flight that has a stop long enough to tour your chosen city. Major stopovers between ORD and HAV include:

    • George Bush Intercontinental Airport (IAH)

    • Miami International Airport (MIA)

    • Cancun International Airport (CUN)

  • ORD is about 40 kilometres from central Chicago. If you're catching a cab, driving or ride-sharing from the centre, it'll take you 35 minutes or so to get there, depending on the traffic. If you're taking public transport, expect the travel time to be around 55 minutes.

  • Planning to catch an early flight from Chicago to Jose Marti International Airport? Avoid the last-minute rush to the terminal (and enjoy a little extra shut-eye) by choosing one of these hotels near O'Hare International Airport:

  • Of all flights departing from O'Hare International Airport, 74.85% land on schedule at their destination.

  • ORD's address is 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 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)

  • MDW is about 19 kilometres from central Chicago. It takes 20 minutes or so to get to the airport in a car from the city centre. Public transport takes roughly 45 minutes.

  • Kick off your holiday early with an extra night away from home. Before your Chicago to HAV flight, unwind in one of these hotels near Chicago Midway International Airport:

  • 77.88% of all departures from Chicago Midway International Airport stick to their scheduled arrival time.

  • You'll find MDW at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • RFD is around 137 kilometres from central Chicago. Driving from the city centre to the terminal takes about 1 hour 25 minutes. If you're planning to use public transport, you can expect a journey of around 4 hours 15 minutes.

  • Relax in bed for a little longer and still make your Chicago to Jose Marti International Airport flight without having to rush. These accommodation options near Chicago Rockford International Airport make departure day a breeze if you're setting off early:

  • Airports have an on-time performance rating that measures how often flights touch down without delays. At RFD, that figure is 76.19%.

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

About Jose Marti International Airport (HAV)

  • If you're coming in on a late flight from Chicago to Jose Marti International Airport, nothing beats 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 options near HAV:

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

  • ₹ 17,067 is the lowest price for a one-way ticket from Chicago to Jose Marti International Airport. A return flight starts at ₹ 29,363. These prices may change depending on availability and demand.

  • Don't wait until the last moment. You're more likely to walk away with cheap flights from Chicago to HAV if you book ahead. Airlines often offer some fantastic early bird discounts.

  • If you're flexible with your trip dates, try using the 'Whole month' search tool. It'll give you the cheapest price in every month when searching for your Chicago to Jose Marti International Airport ticket.

  • You don't need to search every day to find out if prices have dropped when you create a Price Alert. We'll notify you when a better deal is available on flight tickets from Chicago to HAV.

  • Filters make it easier to dig up a deal for your flight from Chicago to Jose Marti International Airport. Choose the airlines, flight times and number of stops that line up with your plans. Then sort the results by 'Cheapest' to zero in on the cheapest fare fast.

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

  • It's time to decide your travel dates for your flight from Chicago to Jose Marti International Airport (HAV). August is the busiest month to travel to Havana. If crowds aren't your thing, go in April.

  • The warmest month in Havana is July, with temperatures ranging between 23ºC and 35ºC. Book your Chicago to HAV flight ticket then if that's your idea of comfortable weather.

  • January sees temperatures of between 17ºC and 28ºC. Search for cheap tickets from Chicago to Jose Marti International Airport around that time if you want to travel when it's cooler.

More about Havana

  • When it comes to searching for somewhere to lay your head, you'll find the top stays in Havana right here. Check out these hotels as soon as you've booked your flight from Chicago to Jose Marti International Airport:

  • Paseo del Malecón and Old Havana are just two of the top attractions to put on your Havana must-do list. Keep the momentum going by heading to La habana.

Explore more of Cuba

  • Havana is easy to fall in love with, but there are so many other corners of Cuba waiting to be explored. Around 257 kilometres east of Havana, a visit to Santa Clara will keep you on the move. Start with popular sights like 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 south-west of Havana. No trip is complete without visiting Parque Nacional Peninsula de Gunanahacabibes, Martí Park and Independencia Park.

Plan the rest of your trip from Chicago to Havana

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